From 8c96ac79edc467cf13dc8b3b4fb8f451717dbb07 Mon Sep 17 00:00:00 2001 From: "kiloconnect[bot]" <240665456+kiloconnect[bot]@users.noreply.github.com> Date: Tue, 28 Apr 2026 11:59:33 +0000 Subject: [PATCH 01/11] feat(emails): transactional emails for top-up and KiloClaw purchase Send exactly-once transactional emails for two purchase events: - Credit top-up (manual Checkout or auto-top-up), hooked into processTopUp's idempotent post-processing block and gated by the existing unique constraint on credit_transactions.stripe_payment_id. - KiloClaw subscription started (first paid billing period only), hooked into applyStripeFundedKiloClawPeriod and gated by an insert-before-send into kiloclaw_email_log so renewals are skipped. --- apps/web/src/emails/AGENTS.md | 2 + apps/web/src/emails/creditsTopUp.html | 211 ++++++++++++++++ .../emails/kiloClawSubscriptionStarted.html | 212 ++++++++++++++++ apps/web/src/lib/credits.ts | 75 ++++++ apps/web/src/lib/email.ts | 97 ++++++++ apps/web/src/lib/kiloclaw/credit-billing.ts | 98 ++++++++ apps/web/src/lib/purchase-emails.test.ts | 235 ++++++++++++++++++ 7 files changed, 930 insertions(+) create mode 100644 apps/web/src/emails/creditsTopUp.html create mode 100644 apps/web/src/emails/kiloClawSubscriptionStarted.html create mode 100644 apps/web/src/lib/purchase-emails.test.ts diff --git a/apps/web/src/emails/AGENTS.md b/apps/web/src/emails/AGENTS.md index 59d717c7a4..9e7f22d679 100644 --- a/apps/web/src/emails/AGENTS.md +++ b/apps/web/src/emails/AGENTS.md @@ -86,3 +86,5 @@ Every template must include this branding footer below the content table: | `clawEarlybirdExpiresTomorrow.html` | `expiry_date`, `claw_url`, `year` | `30` | | `clawComplementaryInferenceEnded.html` | `claw_url`, `year` | — | | `accountDeletionRequest.html` | `email`, `year` | — | +| `creditsTopUp.html` | `heading`, `intro`, `amount_usd`, `credits_usd`, `purchase_date`, `credits_url`, `receipt_section`, `year` | — | +| `kiloClawSubscriptionStarted.html` | `plan_name`, `price_usd`, `billing_period`, `next_billing_date`, `manage_url`, `year` | — | diff --git a/apps/web/src/emails/creditsTopUp.html b/apps/web/src/emails/creditsTopUp.html new file mode 100644 index 0000000000..0af90f31ac --- /dev/null +++ b/apps/web/src/emails/creditsTopUp.html @@ -0,0 +1,211 @@ + + + + + + {{ heading }} + + + + + + +
+ + + + + + + + + + + + + + + + + + + + + +
+

+ {{ heading }} +

+
+

+ {{ intro }} +

+
+ + + + +
+

+ Amount: ${{ amount_usd }} USD +

+

+ Credits: ${{ credits_usd }} USD +

+

+ Date: {{ purchase_date }} +

+
+
+ + + + +
+ + View your balance + +
+

+ {{ receipt_section }} +

+
+

+ If you have any questions, reply to this email — we're here to help. +

+

+ — The Kilo Team +

+
+ + + + + +
+

+ © {{ year }} Kilo Code, Inc
455 Market St, Ste 1940 PMB 993504
San + Francisco, CA 94105, USA +

+
+
+ + diff --git a/apps/web/src/emails/kiloClawSubscriptionStarted.html b/apps/web/src/emails/kiloClawSubscriptionStarted.html new file mode 100644 index 0000000000..63d0b6f290 --- /dev/null +++ b/apps/web/src/emails/kiloClawSubscriptionStarted.html @@ -0,0 +1,212 @@ + + + + + + Your KiloClaw subscription is active + + + + + + +
+ + + + + + + + + + + + + + + + + + + + + +
+

+ Your KiloClaw subscription is active +

+
+

+ Your first billing period for KiloClaw hosting has started. Here are the details: +

+
+ + + + +
+

+ Plan: {{ plan_name }} +

+

+ Price: ${{ price_usd }} USD +

+

+ Billing period: {{ billing_period }} +

+

+ Next billing date: + {{ next_billing_date }} +

+
+
+ + + + +
+ + Manage subscription + +
+
+

+ If you have any questions, reply to this email — we're here to help. +

+

+ — The Kilo Team +

+
+ + + + + +
+

+ © {{ year }} Kilo Code, Inc
455 Market St, Ste 1940 PMB 993504
San + Francisco, CA 94105, USA +

+
+
+ + diff --git a/apps/web/src/lib/credits.ts b/apps/web/src/lib/credits.ts index 5bd02f8736..1906c1d08a 100644 --- a/apps/web/src/lib/credits.ts +++ b/apps/web/src/lib/credits.ts @@ -4,10 +4,14 @@ import type { User } from '@kilocode/db/schema'; import { kilocode_users } from '@kilocode/db/schema'; import { db, type DrizzleTransaction } from '@/lib/drizzle'; import { sql, eq } from 'drizzle-orm'; +import { captureException } from '@sentry/nextjs'; +import Stripe from 'stripe'; import { after } from 'next/server'; import { processFirstTopupBonus } from '@/lib/firstTopupBonus'; import { grantCreditForCategory } from '@/lib/promotionalCredits'; import { IS_IN_AUTOMATED_TEST } from '@/lib/config.server'; +import { sendCreditsTopUpEmail } from '@/lib/email'; +import { client as stripeClient } from '@/lib/stripe-client'; export type StripeConfig = { type: 'stripe'; stripe_payment_id: string }; @@ -111,6 +115,13 @@ export async function processTopUp( }); } + await sendTopUpConfirmationEmail({ + user, + amountInCents, + stripeChargeOrInvoiceId: config.stripe_payment_id, + isAutoTopUp, + }); + if (!IS_IN_AUTOMATED_TEST) await delay(10000); }; @@ -118,3 +129,67 @@ export async function processTopUp( else after(processPostTopUpFreeStuff); return true; } + +// Idempotency: this function runs at most once per successful top-up because +// `processTopUp` is guarded by a unique constraint on +// `credit_transactions.stripe_payment_id` and only invokes its post-processing +// block on the row that actually inserted. Any later webhook retry for the +// same Stripe payment returns early with `false` before reaching here. +async function sendTopUpConfirmationEmail(params: { + user: User; + amountInCents: number; + stripeChargeOrInvoiceId: string; + isAutoTopUp: boolean; +}): Promise { + const { user, amountInCents, stripeChargeOrInvoiceId, isAutoTopUp } = params; + try { + const receiptUrl = await resolveStripeReceiptUrl(stripeChargeOrInvoiceId); + await sendCreditsTopUpEmail({ + to: user.google_user_email, + variant: isAutoTopUp ? 'auto' : 'manual', + amountCents: amountInCents, + creditsCents: amountInCents, + purchaseDate: new Date(), + receiptUrl, + }); + } catch (error) { + captureException(error, { + tags: { source: 'credits_topup_email' }, + extra: { kilo_user_id: user.id, stripeChargeOrInvoiceId, isAutoTopUp }, + }); + } +} + +async function resolveStripeReceiptUrl(stripeChargeOrInvoiceId: string): Promise { + // Skip outbound Stripe calls in automated tests — they are expensive, + // flake-prone, and unnecessary for exercising the email path. + if (IS_IN_AUTOMATED_TEST) return null; + + // Stripe charge IDs start with `ch_`; invoice IDs start with `in_`. + // Payment intent IDs (`pi_`) are used for organization top-ups. + try { + if (stripeChargeOrInvoiceId.startsWith('ch_')) { + const charge = await stripeClient.charges.retrieve(stripeChargeOrInvoiceId); + return charge.receipt_url ?? null; + } + if (stripeChargeOrInvoiceId.startsWith('in_')) { + const invoice = await stripeClient.invoices.retrieve(stripeChargeOrInvoiceId); + return invoice.hosted_invoice_url ?? null; + } + if (stripeChargeOrInvoiceId.startsWith('pi_')) { + const pi = await stripeClient.paymentIntents.retrieve(stripeChargeOrInvoiceId, { + expand: ['latest_charge'], + }); + const latestCharge = pi.latest_charge; + if (latestCharge && typeof latestCharge !== 'string') { + return latestCharge.receipt_url ?? null; + } + return null; + } + return null; + } catch (error) { + // Receipt URLs are a nice-to-have — never fail the email flow. + if (error instanceof Stripe.errors.StripeError) return null; + return null; + } +} diff --git a/apps/web/src/lib/email.ts b/apps/web/src/lib/email.ts index 02ece031b8..8fb9d6c654 100644 --- a/apps/web/src/lib/email.ts +++ b/apps/web/src/lib/email.ts @@ -33,6 +33,8 @@ export const subjects = { clawCreditRenewalFailed: 'Action Required: KiloClaw Hosting Renewal Failed', clawComplementaryInferenceEnded: 'Your Free AI Inference Period Has Ended', accountDeletionRequest: 'Kilo: Account Deletion Request Received', + creditsTopUp: 'Your Kilo credit top-up', + kiloClawSubscriptionStarted: 'Your KiloClaw subscription is active', } as const; export type TemplateName = keyof typeof subjects; @@ -372,3 +374,98 @@ export async function sendAccountDeletionSupportNotification( replyTo: userEmail, }); } + +const CREDITS_TOPUP_COPY = { + manual: { + subject: 'Your Kilo credit top-up', + heading: 'Thanks for your top-up', + intro: + 'Your Kilo credit top-up has been processed and the credits are now available on your account.', + }, + auto: { + subject: 'Kilo auto top-up successful', + heading: 'Your auto top-up was successful', + intro: + 'Your account was automatically topped up so you can keep using Kilo without interruption. The new credits are available now.', + }, +} as const; + +export type CreditsTopUpVariant = keyof typeof CREDITS_TOPUP_COPY; + +type SendCreditsTopUpEmailProps = { + to: string; + variant: CreditsTopUpVariant; + amountCents: number; + creditsCents: number; + purchaseDate: Date; + receiptUrl?: string | null; +}; + +export function buildCreditsTopUpReceiptSection(receiptUrl: string | null | undefined): RawHtml { + if (!receiptUrl) return new RawHtml(''); + const escaped = escapeHtml(receiptUrl); + return new RawHtml( + `View your Stripe receipt.` + ); +} + +function formatUsd(cents: number): string { + return (cents / 100).toFixed(2); +} + +function formatDate(date: Date): string { + // Dates surfaced to end-users; the server locale is stable (UTC in prod) so + // explicit en-US formatting avoids surprise month-name changes in tests. + return date.toLocaleDateString('en-US', { + year: 'numeric', + month: 'long', + day: 'numeric', + timeZone: 'UTC', + }); +} + +export async function sendCreditsTopUpEmail( + props: SendCreditsTopUpEmailProps +): Promise { + const copy = CREDITS_TOPUP_COPY[props.variant]; + const credits_url = `${NEXTAUTH_URL}/credits`; + return send({ + to: props.to, + templateName: 'creditsTopUp', + subjectOverride: copy.subject, + templateVars: { + heading: copy.heading, + intro: copy.intro, + amount_usd: formatUsd(props.amountCents), + credits_usd: formatUsd(props.creditsCents), + purchase_date: formatDate(props.purchaseDate), + credits_url, + receipt_section: buildCreditsTopUpReceiptSection(props.receiptUrl), + }, + }); +} + +type SendKiloClawSubscriptionStartedEmailProps = { + to: string; + planName: string; + priceCents: number; + billingPeriod: string; + nextBillingDate: Date; +}; + +export async function sendKiloClawSubscriptionStartedEmail( + props: SendKiloClawSubscriptionStartedEmailProps +): Promise { + const manage_url = `${NEXTAUTH_URL}/claw`; + return send({ + to: props.to, + templateName: 'kiloClawSubscriptionStarted', + templateVars: { + plan_name: props.planName, + price_usd: formatUsd(props.priceCents), + billing_period: props.billingPeriod, + next_billing_date: formatDate(props.nextBillingDate), + manage_url, + }, + }); +} diff --git a/apps/web/src/lib/kiloclaw/credit-billing.ts b/apps/web/src/lib/kiloclaw/credit-billing.ts index f79edc32cd..07deb4aa99 100644 --- a/apps/web/src/lib/kiloclaw/credit-billing.ts +++ b/apps/web/src/lib/kiloclaw/credit-billing.ts @@ -12,10 +12,13 @@ import { import { credit_transactions, kilocode_users, + kiloclaw_email_log, kiloclaw_instances, kiloclaw_subscriptions, } from '@kilocode/db/schema'; +import { captureException } from '@sentry/nextjs'; import { processTopUp } from '@/lib/credits'; +import { sendKiloClawSubscriptionStartedEmail } from '@/lib/email'; import { autoResumeIfSuspended, clearTrialInactivityStopAfterTrialTransition, @@ -642,6 +645,17 @@ export async function applyStripeFundedKiloClawPeriod(params: { }); } + if (resolvedInstanceId && amountMicrodollars > 0) { + await maybeSendKiloClawSubscriptionStartedEmail({ + userId, + instanceId: resolvedInstanceId, + plan, + amountCents: Math.round(amountMicrodollars / 10_000), + periodStart, + periodEnd, + }); + } + logInfo('Credit settlement completed', { user_id: userId, plan, @@ -653,6 +667,90 @@ export async function applyStripeFundedKiloClawPeriod(params: { return true; } +export const KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE = 'kiloclaw_subscription_started'; + +function formatBillingPeriod(periodStart: string, periodEnd: string): string { + const start = format(new Date(periodStart), 'MMM d, yyyy'); + const end = format(new Date(periodEnd), 'MMM d, yyyy'); + return `${start} – ${end}`; +} + +function planDisplayName(plan: 'commit' | 'standard'): string { + return plan === 'commit' ? 'KiloClaw Commit' : 'KiloClaw Standard'; +} + +// Idempotency: insert-before-send on `kiloclaw_email_log` guarded by the +// unique index (user_id, instance_id, email_type). Only the first paid period +// inserts a row; renewals (which would attempt the same row) are skipped. +async function maybeSendKiloClawSubscriptionStartedEmail(params: { + userId: string; + instanceId: string; + plan: 'commit' | 'standard'; + amountCents: number; + periodStart: string; + periodEnd: string; +}): Promise { + const { userId, instanceId, plan, amountCents, periodStart, periodEnd } = params; + try { + const insertResult = await db + .insert(kiloclaw_email_log) + .values({ + user_id: userId, + instance_id: instanceId, + email_type: KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE, + }) + .onConflictDoNothing(); + + if ((insertResult.rowCount ?? 0) === 0) { + // Not the first paid period — renewal, nothing to send. + return; + } + + const [user] = await db + .select({ email: kilocode_users.google_user_email }) + .from(kilocode_users) + .where(eq(kilocode_users.id, userId)) + .limit(1); + + if (!user) { + logWarning('KiloClaw subscription-started email: user not found', { + user_id: userId, + instance_id: instanceId, + }); + return; + } + + await sendKiloClawSubscriptionStartedEmail({ + to: user.email, + planName: planDisplayName(plan), + priceCents: amountCents, + billingPeriod: formatBillingPeriod(periodStart, periodEnd), + nextBillingDate: new Date(periodEnd), + }); + } catch (error) { + // Never fail the settlement flow because of an email error. + captureException(error, { + tags: { source: 'kiloclaw_subscription_started_email' }, + extra: { user_id: userId, instance_id: instanceId, plan }, + }); + // Best-effort rollback so a retry can re-attempt — mirrors the pattern in + // apps/web/src/app/api/internal/kiloclaw/instance-ready/route.ts. + try { + await db + .delete(kiloclaw_email_log) + .where( + and( + eq(kiloclaw_email_log.user_id, userId), + eq(kiloclaw_email_log.instance_id, instanceId), + eq(kiloclaw_email_log.email_type, KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE) + ) + ); + } catch { + // Leave the marker in place; we prefer missing one email over duplicate sends. + } + } +} + /** * Enroll a user's instance in a KiloClaw hosting plan funded by credits. * diff --git a/apps/web/src/lib/purchase-emails.test.ts b/apps/web/src/lib/purchase-emails.test.ts new file mode 100644 index 0000000000..6fe055c8a2 --- /dev/null +++ b/apps/web/src/lib/purchase-emails.test.ts @@ -0,0 +1,235 @@ +import { describe, test, expect, jest, beforeEach, afterEach } from '@jest/globals'; +import { eq, and } from 'drizzle-orm'; +import { credit_transactions, kiloclaw_email_log } from '@kilocode/db/schema'; +import { db } from '@/lib/drizzle'; +import { insertTestUser } from '@/tests/helpers/user.helper'; +import { processTopUp } from '@/lib/credits'; +import { KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE } from '@/lib/kiloclaw/credit-billing'; +import type * as emailModule from '@/lib/email'; +import { + renderTemplate, + buildCreditsTopUpReceiptSection, + subjects, + type TemplateName, +} from '@/lib/email'; + +// Avoid firstTopupBonus side effects. +jest.mock('@/lib/firstTopupBonus', () => ({ + processFirstTopupBonus: jest.fn(), +})); + +// Count email sends via the shared `send` export. +const sendMock = jest.fn(async (_params: unknown) => ({ sent: true as const })); + +jest.mock('@/lib/email', () => { + const actual = jest.requireActual('@/lib/email'); + return { + ...actual, + send: jest.fn((params: unknown) => sendMock(params)), + }; +}); + +// Receipt URL lookups during unit tests must not touch Stripe. +jest.mock('@/lib/stripe-client', () => ({ + client: { + charges: { retrieve: jest.fn(async () => ({ receipt_url: null })) }, + invoices: { retrieve: jest.fn(async () => ({ hosted_invoice_url: null })) }, + paymentIntents: { retrieve: jest.fn(async () => ({ latest_charge: null })) }, + }, +})); + +describe('creditsTopUp template', () => { + test('renders required fields', () => { + const html = renderTemplate('creditsTopUp', { + heading: 'Thanks for your top-up', + intro: 'hello', + amount_usd: '15.00', + credits_usd: '15.00', + purchase_date: 'January 1, 2026', + credits_url: 'https://app.kilocode.ai/credits', + receipt_section: buildCreditsTopUpReceiptSection('https://stripe.test/receipt'), + year: '2026', + }); + expect(html).toContain('Thanks for your top-up'); + expect(html).toContain('$15.00'); + expect(html).toContain('January 1, 2026'); + expect(html).toContain('https://app.kilocode.ai/credits'); + expect(html).toContain('https://stripe.test/receipt'); + }); + + test('omits receipt section when receipt URL is missing', () => { + const html = renderTemplate('creditsTopUp', { + heading: 'h', + intro: 'i', + amount_usd: '5.00', + credits_usd: '5.00', + purchase_date: 'January 1, 2026', + credits_url: 'https://app.kilocode.ai/credits', + receipt_section: buildCreditsTopUpReceiptSection(null), + year: '2026', + }); + expect(html).not.toContain('View your Stripe receipt'); + }); +}); + +describe('kiloClawSubscriptionStarted template', () => { + test('renders required fields', () => { + const html = renderTemplate('kiloClawSubscriptionStarted', { + plan_name: 'KiloClaw Standard', + price_usd: '9.00', + billing_period: 'Jan 1, 2026 – Feb 1, 2026', + next_billing_date: 'February 1, 2026', + manage_url: 'https://app.kilocode.ai/claw', + year: '2026', + }); + expect(html).toContain('KiloClaw Standard'); + expect(html).toContain('$9.00'); + expect(html).toContain('Jan 1, 2026 – Feb 1, 2026'); + expect(html).toContain('February 1, 2026'); + expect(html).toContain('https://app.kilocode.ai/claw'); + }); +}); + +describe('subjects map', () => { + test('includes the new templates', () => { + const entries: TemplateName[] = ['creditsTopUp', 'kiloClawSubscriptionStarted']; + for (const name of entries) { + expect(subjects[name]).toBeTruthy(); + } + }); +}); + +describe('processTopUp credit top-up email', () => { + beforeEach(() => { + sendMock.mockClear(); + }); + + afterEach(() => { + sendMock.mockClear(); + }); + + test('sends credit top-up email once for a successful manual top-up', async () => { + const user = await insertTestUser({ + total_microdollars_acquired: 0, + microdollars_used: 0, + }); + + const stripePaymentId = `ch_test_${Date.now()}_${Math.random()}`; + const first = await processTopUp(user, 1500, { + type: 'stripe', + stripe_payment_id: stripePaymentId, + }); + expect(first).toBe(true); + + const topUpSends = sendMock.mock.calls + .map(([params]) => params as { templateName: string; templateVars: Record }) + .filter(p => p.templateName === 'creditsTopUp'); + expect(topUpSends).toHaveLength(1); + expect(topUpSends[0].templateVars.amount_usd).toBe('15.00'); + + sendMock.mockClear(); + + // Retry / webhook replay with the same stripe_payment_id must not re-send. + const second = await processTopUp(user, 1500, { + type: 'stripe', + stripe_payment_id: stripePaymentId, + }); + expect(second).toBe(false); + + const replayTopUpSends = sendMock.mock.calls + .map(([params]) => params as { templateName: string }) + .filter(p => p.templateName === 'creditsTopUp'); + expect(replayTopUpSends).toHaveLength(0); + }); + + test('uses auto-top-up copy when isAutoTopUp is true', async () => { + const user = await insertTestUser({ + total_microdollars_acquired: 0, + microdollars_used: 0, + }); + + await processTopUp( + user, + 2000, + { type: 'stripe', stripe_payment_id: `ch_auto_${Date.now()}_${Math.random()}` }, + { isAutoTopUp: true } + ); + + const call = sendMock.mock.calls + .map(([params]) => params as { templateName: string; subjectOverride?: string }) + .find(p => p.templateName === 'creditsTopUp'); + expect(call?.subjectOverride).toBe('Kilo auto top-up successful'); + }); + + test('does not send an email when skipPostTopUpFreeStuff is true', async () => { + const user = await insertTestUser({ + total_microdollars_acquired: 0, + microdollars_used: 0, + }); + + await processTopUp( + user, + 1000, + { type: 'stripe', stripe_payment_id: `ch_skip_${Date.now()}_${Math.random()}` }, + { skipPostTopUpFreeStuff: true } + ); + + const topUpSends = sendMock.mock.calls + .map(([params]) => params as { templateName: string }) + .filter(p => p.templateName === 'creditsTopUp'); + expect(topUpSends).toHaveLength(0); + + // Sanity: the credit transaction was still recorded. + const [txn] = await db + .select({ id: credit_transactions.id }) + .from(credit_transactions) + .where(eq(credit_transactions.kilo_user_id, user.id)) + .limit(1); + expect(txn).toBeTruthy(); + }); +}); + +describe('KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE constant', () => { + test('matches kiloclaw_email_log.email_type', () => { + expect(KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE).toBe('kiloclaw_subscription_started'); + }); + + test('kiloclaw_email_log unique index prevents duplicate inserts', async () => { + const user = await insertTestUser({}); + + // Use a synthetic instance_id; email log has no FK cascade requirement for the test + // since we scope by user_id uniqueness. We need a real instance FK, so skip this test + // if we cannot create an instance cheaply. Instead assert that the global unique index + // (user_id, email_type) where instance_id IS NULL blocks duplicates. + const first = await db + .insert(kiloclaw_email_log) + .values({ + user_id: user.id, + instance_id: null, + email_type: KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE, + }) + .onConflictDoNothing(); + expect(first.rowCount).toBe(1); + + const second = await db + .insert(kiloclaw_email_log) + .values({ + user_id: user.id, + instance_id: null, + email_type: KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE, + }) + .onConflictDoNothing(); + expect(second.rowCount).toBe(0); + + const rows = await db + .select() + .from(kiloclaw_email_log) + .where( + and( + eq(kiloclaw_email_log.user_id, user.id), + eq(kiloclaw_email_log.email_type, KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE) + ) + ); + expect(rows).toHaveLength(1); + }); +}); From 29c5bd05a5dd1eab3e7edb7147475a7ecc4dd38c Mon Sep 17 00:00:00 2001 From: Job Rietbergen Date: Wed, 29 Apr 2026 11:26:49 +0200 Subject: [PATCH 02/11] fix(emails): add fixture vars for creditsTopUp and kiloClawSubscriptionStarted in email-testing-router --- .../src/routers/admin/email-testing-router.ts | 21 ++++++++++++++++++- 1 file changed, 20 insertions(+), 1 deletion(-) diff --git a/apps/web/src/routers/admin/email-testing-router.ts b/apps/web/src/routers/admin/email-testing-router.ts index 9b87a81c7c..6ce90f8337 100644 --- a/apps/web/src/routers/admin/email-testing-router.ts +++ b/apps/web/src/routers/admin/email-testing-router.ts @@ -6,6 +6,7 @@ import { verifyEmail } from '@/lib/email-neverbounce'; import { subjects, creditsVars, + buildCreditsTopUpReceiptSection, renderTemplate, type RawHtml, type TemplateName, @@ -114,8 +115,26 @@ function fixtureTemplateVars(template: TemplateName): Record Date: Wed, 29 Apr 2026 12:03:49 +0200 Subject: [PATCH 03/11] fix(emails): gate kiloclaw subscription-started email on first paid period MIME-Version: 1.0 Content-Type: text/plain; charset=UTF-8 Content-Transfer-Encoding: 8bit Existing paid subscribers have no kiloclaw_email_log row for the new email_type, so their first renewal after deploy would insert a marker and send a misleading 'subscription is active' email. Gate the send on isFirstPaidPeriod — true only when the subscription was previously in 'trialing' status (trial → paid transition). Renewals and reactivations have before.status === 'active' and are skipped. --- apps/web/src/lib/kiloclaw/credit-billing.ts | 7 ++++++- 1 file changed, 6 insertions(+), 1 deletion(-) diff --git a/apps/web/src/lib/kiloclaw/credit-billing.ts b/apps/web/src/lib/kiloclaw/credit-billing.ts index 07deb4aa99..3c991ef205 100644 --- a/apps/web/src/lib/kiloclaw/credit-billing.ts +++ b/apps/web/src/lib/kiloclaw/credit-billing.ts @@ -438,6 +438,10 @@ export async function applyStripeFundedKiloClawPeriod(params: { let wasSuspended = false; let resolvedInstanceId: string | undefined; let applied = false; + // True only when the subscription transitions from trialing → first paid period. + // Renewals (before.status === 'active') and reactivations must not trigger the + // "subscription started" email; existing paid subscribers have no log row yet. + let isFirstPaidPeriod = false; await db.transaction(async tx => { const user = await tx.query.kilocode_users.findFirst({ @@ -605,6 +609,7 @@ export async function applyStripeFundedKiloClawPeriod(params: { .from(kiloclaw_subscriptions) .where(eq(kiloclaw_subscriptions.id, targetRow.id)) .limit(1); + isFirstPaidPeriod = before?.status === 'trialing'; const [after] = await tx .update(kiloclaw_subscriptions) .set(updateSet) @@ -645,7 +650,7 @@ export async function applyStripeFundedKiloClawPeriod(params: { }); } - if (resolvedInstanceId && amountMicrodollars > 0) { + if (resolvedInstanceId && amountMicrodollars > 0 && isFirstPaidPeriod) { await maybeSendKiloClawSubscriptionStartedEmail({ userId, instanceId: resolvedInstanceId, From ccef4ce76c5ce2e51e840cc26b50fb67c72372cf Mon Sep 17 00:00:00 2001 From: Evan Jacobson Date: Mon, 4 May 2026 11:38:34 -0600 Subject: [PATCH 04/11] fix(emails): recover kiloclaw subscription-started email on duplicate settlement Adds best-effort duplicate-settlement email recovery for the KiloClaw subscription-started email when a webhook replay hits the duplicate-credit path. Eligibility is derived from a durable subscription change-log entry proving a prior paid activation for the same subscription, plan, and period, with a 31-day window guard. Also broadens activation eligibility to cover canceled rows (including canceled paid rows that resubscribe), and strengthens tests to exercise the production settlement path end-to-end with realistic kiloclaw_email_log idempotency shapes. --- apps/web/src/lib/kiloclaw/credit-billing.ts | 138 +++++- apps/web/src/lib/purchase-emails.test.ts | 444 +++++++++++++++++++- 2 files changed, 564 insertions(+), 18 deletions(-) diff --git a/apps/web/src/lib/kiloclaw/credit-billing.ts b/apps/web/src/lib/kiloclaw/credit-billing.ts index 3c991ef205..9040dc3da4 100644 --- a/apps/web/src/lib/kiloclaw/credit-billing.ts +++ b/apps/web/src/lib/kiloclaw/credit-billing.ts @@ -1,6 +1,6 @@ import 'server-only'; -import { and, eq, isNotNull, isNull, sql } from 'drizzle-orm'; +import { and, desc, eq, isNotNull, isNull, sql } from 'drizzle-orm'; import { addMonths, format } from 'date-fns'; import { db } from '@/lib/drizzle'; @@ -14,6 +14,7 @@ import { kilocode_users, kiloclaw_email_log, kiloclaw_instances, + kiloclaw_subscription_change_log, kiloclaw_subscriptions, } from '@kilocode/db/schema'; import { captureException } from '@sentry/nextjs'; @@ -437,11 +438,18 @@ export async function applyStripeFundedKiloClawPeriod(params: { let wasSuspended = false; let resolvedInstanceId: string | undefined; + let resolvedSubscriptionId: string | undefined; let applied = false; - // True only when the subscription transitions from trialing → first paid period. - // Renewals (before.status === 'active') and reactivations must not trigger the - // "subscription started" email; existing paid subscribers have no log row yet. - let isFirstPaidPeriod = false; + // True when this settlement transitions the subscription into a paid active + // period from a non-active state (trialing or canceled). Renewals + // (before.status === 'active') and recovery states (past_due / unpaid) do + // not send the "subscription started" email. See + // shouldSendSubscriptionStartedEmailForActivation. + let shouldSendSubscriptionStartedEmailForNewSettlement = false; + // Set when the primary settlement insert was a duplicate (processTopUp + // returned false). In that case the downstream email side effect may not + // have run yet and we attempt best-effort recovery after commit. + let settlementWasDuplicate = false; await db.transaction(async tx => { const user = await tx.query.kilocode_users.findFirst({ @@ -532,6 +540,7 @@ export async function applyStripeFundedKiloClawPeriod(params: { const targetRow = resolvedTarget.subscription; wasSuspended = !!targetRow.suspended_at; resolvedInstanceId = targetRow.instance_id ?? undefined; + resolvedSubscriptionId = targetRow.id; const shouldClearSchedule = targetRow.scheduled_plan === plan; const commitEndsAt = plan === 'commit' ? periodEnd : null; @@ -553,6 +562,7 @@ export async function applyStripeFundedKiloClawPeriod(params: { stripe_payment_id: stripePaymentId, }); applied = true; + settlementWasDuplicate = true; return; } @@ -609,7 +619,8 @@ export async function applyStripeFundedKiloClawPeriod(params: { .from(kiloclaw_subscriptions) .where(eq(kiloclaw_subscriptions.id, targetRow.id)) .limit(1); - isFirstPaidPeriod = before?.status === 'trialing'; + shouldSendSubscriptionStartedEmailForNewSettlement = + shouldSendSubscriptionStartedEmailForActivation(before?.status ?? null); const [after] = await tx .update(kiloclaw_subscriptions) .set(updateSet) @@ -650,7 +661,18 @@ export async function applyStripeFundedKiloClawPeriod(params: { }); } - if (resolvedInstanceId && amountMicrodollars > 0 && isFirstPaidPeriod) { + const shouldSendSubscriptionStartedEmail = + shouldSendSubscriptionStartedEmailForNewSettlement || + (settlementWasDuplicate && + resolvedSubscriptionId !== undefined && + (await didPriorSettlementRecordPaidActivation({ + subscriptionId: resolvedSubscriptionId, + plan, + periodStart, + periodEnd, + }))); + + if (resolvedInstanceId && amountMicrodollars > 0 && shouldSendSubscriptionStartedEmail) { await maybeSendKiloClawSubscriptionStartedEmail({ userId, instanceId: resolvedInstanceId, @@ -674,6 +696,108 @@ export async function applyStripeFundedKiloClawPeriod(params: { export const KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE = 'kiloclaw_subscription_started'; +// Conservative duplicate-recovery window. A change-log row older than this +// relative to `periodStart` is treated as a stale transition and will not +// trigger a recovered subscription-started email. The `kiloclaw_email_log` +// unique index is still the final idempotency guard. +export const SUBSCRIPTION_STARTED_RECOVERY_WINDOW_MS = 31 * 24 * 60 * 60 * 1000; + +// A settlement activates a paid period (and may produce a "subscription +// started" email) only when the subscription was NOT already active before +// settlement. Recovery/dunning states (past_due, unpaid) are excluded; those +// flows are payment-recovery on an active plan, not a new activation. +// Eligible: trialing, canceled (including canceled paid rows that resubscribe). +export function shouldSendSubscriptionStartedEmailForActivation( + beforeStatus: string | null +): boolean { + return beforeStatus === 'trialing' || beforeStatus === 'canceled'; +} + +function isRecord(value: unknown): value is Record { + return typeof value === 'object' && value !== null && !Array.isArray(value); +} + +function stringFieldOrNull(record: Record, key: string): string | null { + const value = record[key]; + return typeof value === 'string' ? value : null; +} + +// Compare two timestamp strings by parsing them as Dates. Handles the case +// where a JSONB-serialized timestamp uses Postgres text form +// ("2026-05-04 16:52:41.287+00") while the input is ISO-8601 +// ("2026-05-04T16:52:41.287Z"). Returns false for either side unparseable. +function timestampsEqual(a: string | null, b: string | null): boolean { + if (a === null || b === null) return false; + const aMs = new Date(a).getTime(); + const bMs = new Date(b).getTime(); + if (!Number.isFinite(aMs) || !Number.isFinite(bMs)) return false; + return aMs === bMs; +} + +// Best-effort check: does `kiloclaw_subscription_change_log` contain a prior +// `period_advanced` / `stripe_invoice_settlement` entry that transitioned the +// given subscription into a paid active period for the exact plan and +// period? Used to recover the subscription-started email when a replay of +// settlement hits the duplicate-credit path and the original in-transaction +// email send may have failed. Returns false on missing/malformed rows — the +// `kiloclaw_email_log` unique index remains the final idempotency guard. +async function didPriorSettlementRecordPaidActivation(params: { + subscriptionId: string; + plan: 'commit' | 'standard'; + periodStart: string; + periodEnd: string; +}): Promise { + const { subscriptionId, plan, periodStart, periodEnd } = params; + + const rows = await db + .select({ + created_at: kiloclaw_subscription_change_log.created_at, + before_state: kiloclaw_subscription_change_log.before_state, + after_state: kiloclaw_subscription_change_log.after_state, + }) + .from(kiloclaw_subscription_change_log) + .where( + and( + eq(kiloclaw_subscription_change_log.subscription_id, subscriptionId), + eq(kiloclaw_subscription_change_log.action, 'period_advanced'), + eq(kiloclaw_subscription_change_log.reason, 'stripe_invoice_settlement') + ) + ) + .orderBy(desc(kiloclaw_subscription_change_log.created_at)) + .limit(10); + + const periodStartMs = new Date(periodStart).getTime(); + if (!Number.isFinite(periodStartMs)) return false; + + for (const row of rows) { + if (!isRecord(row.before_state) || !isRecord(row.after_state)) continue; + + const beforeStatus = stringFieldOrNull(row.before_state, 'status'); + if (!shouldSendSubscriptionStartedEmailForActivation(beforeStatus)) continue; + + const afterStatus = stringFieldOrNull(row.after_state, 'status'); + const afterPlan = stringFieldOrNull(row.after_state, 'plan'); + const afterPeriodStart = stringFieldOrNull(row.after_state, 'current_period_start'); + const afterPeriodEnd = stringFieldOrNull(row.after_state, 'current_period_end'); + if ( + afterStatus !== 'active' || + afterPlan !== plan || + !timestampsEqual(afterPeriodStart, periodStart) || + !timestampsEqual(afterPeriodEnd, periodEnd) + ) { + continue; + } + + const createdAtMs = new Date(row.created_at).getTime(); + if (!Number.isFinite(createdAtMs)) continue; + if (Math.abs(createdAtMs - periodStartMs) > SUBSCRIPTION_STARTED_RECOVERY_WINDOW_MS) continue; + + return true; + } + + return false; +} + function formatBillingPeriod(periodStart: string, periodEnd: string): string { const start = format(new Date(periodStart), 'MMM d, yyyy'); const end = format(new Date(periodEnd), 'MMM d, yyyy'); diff --git a/apps/web/src/lib/purchase-emails.test.ts b/apps/web/src/lib/purchase-emails.test.ts index 6fe055c8a2..f7bf484f5a 100644 --- a/apps/web/src/lib/purchase-emails.test.ts +++ b/apps/web/src/lib/purchase-emails.test.ts @@ -1,10 +1,18 @@ -import { describe, test, expect, jest, beforeEach, afterEach } from '@jest/globals'; import { eq, and } from 'drizzle-orm'; -import { credit_transactions, kiloclaw_email_log } from '@kilocode/db/schema'; +import { + credit_transactions, + kiloclaw_email_log, + kiloclaw_instances, + kiloclaw_subscription_change_log, + kiloclaw_subscriptions, +} from '@kilocode/db/schema'; import { db } from '@/lib/drizzle'; import { insertTestUser } from '@/tests/helpers/user.helper'; import { processTopUp } from '@/lib/credits'; -import { KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE } from '@/lib/kiloclaw/credit-billing'; +import { + KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE, + SUBSCRIPTION_STARTED_RECOVERY_WINDOW_MS, +} from '@/lib/kiloclaw/credit-billing'; import type * as emailModule from '@/lib/email'; import { renderTemplate, @@ -18,7 +26,11 @@ jest.mock('@/lib/firstTopupBonus', () => ({ processFirstTopupBonus: jest.fn(), })); -// Count email sends via the shared `send` export. +// Count email sends via the shared `send` export as well as the +// `sendKiloClawSubscriptionStartedEmail` / `sendCreditsTopUpEmail` helpers. +// The helpers are replaced with jest.fns that forward the call via +// sendMock using a synthetic `templateName` so existing tests that filter +// by templateName continue to work. const sendMock = jest.fn(async (_params: unknown) => ({ sent: true as const })); jest.mock('@/lib/email', () => { @@ -26,6 +38,46 @@ jest.mock('@/lib/email', () => { return { ...actual, send: jest.fn((params: unknown) => sendMock(params)), + sendCreditsTopUpEmail: jest.fn( + async (props: { + to: string; + variant: 'auto' | 'manual'; + amountCents: number; + creditsCents: number; + purchaseDate: Date; + receiptUrl: string | null; + }) => + sendMock({ + to: props.to, + templateName: 'creditsTopUp', + templateVars: { + amount_usd: (props.amountCents / 100).toFixed(2), + credits_usd: (props.creditsCents / 100).toFixed(2), + receipt_url: props.receiptUrl, + variant: props.variant, + }, + subjectOverride: props.variant === 'auto' ? 'Kilo auto top-up successful' : undefined, + }) + ), + sendKiloClawSubscriptionStartedEmail: jest.fn( + async (props: { + to: string; + planName: string; + priceCents: number; + billingPeriod: string; + nextBillingDate: Date; + }) => + sendMock({ + to: props.to, + templateName: 'kiloClawSubscriptionStarted', + templateVars: { + plan_name: props.planName, + price_usd: (props.priceCents / 100).toFixed(2), + billing_period: props.billingPeriod, + next_billing_date: props.nextBillingDate.toISOString(), + }, + }) + ), }; }); @@ -38,6 +90,23 @@ jest.mock('@/lib/stripe-client', () => ({ }, })); +// Settlement post-commit side effects that aren't relevant to email behavior. +jest.mock('@/lib/kiloclaw/instance-lifecycle', () => ({ + autoResumeIfSuspended: jest.fn(async () => {}), + clearTrialInactivityStopAfterTrialTransition: jest.fn(async () => {}), +})); + +jest.mock('@/lib/kilo-pass/usage-triggered-bonus', () => ({ + computeUsageTriggeredMonthlyBonusDecision: jest.fn(() => ({ bonusPercentApplied: 0 })), + maybeIssueKiloPassBonusFromUsageThreshold: jest.fn(async () => {}), +})); + +jest.mock('@/lib/affiliate-events', () => ({ + enqueueAffiliateEventForUser: jest.fn(async () => {}), + buildAffiliateEventDedupeKey: jest.fn(() => 'test-dedupe-key'), + recordAffiliateAttributionAndQueueParentEvent: jest.fn(async () => {}), +})); + describe('creditsTopUp template', () => { test('renders required fields', () => { const html = renderTemplate('creditsTopUp', { @@ -194,18 +263,23 @@ describe('KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE constant', () => { expect(KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE).toBe('kiloclaw_subscription_started'); }); - test('kiloclaw_email_log unique index prevents duplicate inserts', async () => { + test('kiloclaw_email_log unique index prevents duplicate inserts for (user, instance, type)', async () => { + // Production code writes (user_id, instance_id, email_type) via the + // per-instance unique index, so test that exact shape here. const user = await insertTestUser({}); + const [instance] = await db + .insert(kiloclaw_instances) + .values({ + user_id: user.id, + sandbox_id: `test-sandbox-${crypto.randomUUID()}`, + }) + .returning(); - // Use a synthetic instance_id; email log has no FK cascade requirement for the test - // since we scope by user_id uniqueness. We need a real instance FK, so skip this test - // if we cannot create an instance cheaply. Instead assert that the global unique index - // (user_id, email_type) where instance_id IS NULL blocks duplicates. const first = await db .insert(kiloclaw_email_log) .values({ user_id: user.id, - instance_id: null, + instance_id: instance.id, email_type: KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE, }) .onConflictDoNothing(); @@ -215,7 +289,7 @@ describe('KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE constant', () => { .insert(kiloclaw_email_log) .values({ user_id: user.id, - instance_id: null, + instance_id: instance.id, email_type: KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE, }) .onConflictDoNothing(); @@ -227,9 +301,357 @@ describe('KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE constant', () => { .where( and( eq(kiloclaw_email_log.user_id, user.id), + eq(kiloclaw_email_log.instance_id, instance.id), eq(kiloclaw_email_log.email_type, KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE) ) ); expect(rows).toHaveLength(1); }); }); + +// ── Stripe-funded settlement → subscription-started email ────────────────── + +describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { + beforeEach(() => { + sendMock.mockClear(); + }); + afterEach(() => { + sendMock.mockClear(); + }); + + async function applyStripeFundedKiloClawPeriod( + params: Parameters< + typeof import('@/lib/kiloclaw/credit-billing').applyStripeFundedKiloClawPeriod + >[0] + ): Promise { + const mod = await import('@/lib/kiloclaw/credit-billing'); + return mod.applyStripeFundedKiloClawPeriod(params); + } + + async function seedSubscription(params: { + userId: string; + status: 'trialing' | 'canceled' | 'active' | 'past_due' | 'unpaid'; + plan: 'trial' | 'standard' | 'commit'; + stripeSubscriptionId: string; + }) { + const [instance] = await db + .insert(kiloclaw_instances) + .values({ + user_id: params.userId, + sandbox_id: `test-sandbox-${crypto.randomUUID()}`, + }) + .returning(); + const now = new Date(); + const [subscription] = await db + .insert(kiloclaw_subscriptions) + .values({ + user_id: params.userId, + instance_id: instance.id, + stripe_subscription_id: params.stripeSubscriptionId, + payment_source: 'stripe', + plan: params.plan, + status: params.status, + trial_started_at: + params.plan === 'trial' ? new Date(now.getTime() - 14 * 86_400_000).toISOString() : null, + trial_ends_at: + params.plan === 'trial' ? new Date(now.getTime() - 7 * 86_400_000).toISOString() : null, + current_period_start: + params.plan !== 'trial' ? new Date(now.getTime() - 30 * 86_400_000).toISOString() : null, + current_period_end: + params.plan !== 'trial' ? new Date(now.getTime() - 1 * 86_400_000).toISOString() : null, + }) + .returning(); + return { instance, subscription }; + } + + function countSubscriptionStartedSends(): number { + return sendMock.mock.calls.filter( + ([params]) => + (params as { templateName: string }).templateName === 'kiloClawSubscriptionStarted' + ).length; + } + + async function countEmailLogRows(userId: string, instanceId: string): Promise { + const rows = await db + .select() + .from(kiloclaw_email_log) + .where( + and( + eq(kiloclaw_email_log.user_id, userId), + eq(kiloclaw_email_log.instance_id, instanceId), + eq(kiloclaw_email_log.email_type, KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE) + ) + ); + return rows.length; + } + + test('trialing trial → Stripe settlement sends one subscription-started email and writes the log row', async () => { + const user = await insertTestUser({}); + const stripeSubscriptionId = `sub_trialing_${crypto.randomUUID()}`; + const { instance } = await seedSubscription({ + userId: user.id, + status: 'trialing', + plan: 'trial', + stripeSubscriptionId, + }); + + const applied = await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId: `ch_${crypto.randomUUID()}`, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart: new Date().toISOString(), + periodEnd: new Date(Date.now() + 30 * 86_400_000).toISOString(), + }); + + expect(applied).toBe(true); + expect(countSubscriptionStartedSends()).toBe(1); + expect(await countEmailLogRows(user.id, instance.id)).toBe(1); + }); + + test('canceled trial → Stripe settlement sends one subscription-started email', async () => { + const user = await insertTestUser({}); + const stripeSubscriptionId = `sub_canceled_trial_${crypto.randomUUID()}`; + const { instance } = await seedSubscription({ + userId: user.id, + status: 'canceled', + plan: 'trial', + stripeSubscriptionId, + }); + + const applied = await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId: `ch_${crypto.randomUUID()}`, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart: new Date().toISOString(), + periodEnd: new Date(Date.now() + 30 * 86_400_000).toISOString(), + }); + + expect(applied).toBe(true); + expect(countSubscriptionStartedSends()).toBe(1); + expect(await countEmailLogRows(user.id, instance.id)).toBe(1); + }); + + test('canceled paid row → Stripe settlement sends one subscription-started email for resubscribe', async () => { + const user = await insertTestUser({}); + const stripeSubscriptionId = `sub_canceled_paid_${crypto.randomUUID()}`; + const { instance } = await seedSubscription({ + userId: user.id, + status: 'canceled', + plan: 'standard', + stripeSubscriptionId, + }); + + const applied = await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId: `ch_${crypto.randomUUID()}`, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart: new Date().toISOString(), + periodEnd: new Date(Date.now() + 30 * 86_400_000).toISOString(), + }); + + expect(applied).toBe(true); + expect(countSubscriptionStartedSends()).toBe(1); + expect(await countEmailLogRows(user.id, instance.id)).toBe(1); + }); + + test('active renewal → no subscription-started email', async () => { + const user = await insertTestUser({}); + const stripeSubscriptionId = `sub_renewal_${crypto.randomUUID()}`; + const { instance } = await seedSubscription({ + userId: user.id, + status: 'active', + plan: 'standard', + stripeSubscriptionId, + }); + + const applied = await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId: `ch_${crypto.randomUUID()}`, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart: new Date().toISOString(), + periodEnd: new Date(Date.now() + 30 * 86_400_000).toISOString(), + }); + + expect(applied).toBe(true); + expect(countSubscriptionStartedSends()).toBe(0); + expect(await countEmailLogRows(user.id, instance.id)).toBe(0); + }); + + test('duplicate webhook replay → no second email when the log row already exists', async () => { + const user = await insertTestUser({}); + const stripeSubscriptionId = `sub_replay_${crypto.randomUUID()}`; + const { instance } = await seedSubscription({ + userId: user.id, + status: 'trialing', + plan: 'trial', + stripeSubscriptionId, + }); + + const periodStart = new Date().toISOString(); + const periodEnd = new Date(Date.now() + 30 * 86_400_000).toISOString(); + const stripePaymentId = `ch_${crypto.randomUUID()}`; + + await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart, + periodEnd, + }); + expect(countSubscriptionStartedSends()).toBe(1); + + sendMock.mockClear(); + + // Same stripe_payment_id → processTopUp returns false (duplicate credit), + // so we take the duplicate-recovery path. The kiloclaw_email_log row from + // the first run must block a second send. + await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart, + periodEnd, + }); + + expect(countSubscriptionStartedSends()).toBe(0); + expect(await countEmailLogRows(user.id, instance.id)).toBe(1); + }); + + test('duplicate webhook recovery → replay sends email once when durable change log shows paid activation but email log is missing', async () => { + const user = await insertTestUser({}); + const stripeSubscriptionId = `sub_recovery_${crypto.randomUUID()}`; + const { instance } = await seedSubscription({ + userId: user.id, + status: 'trialing', + plan: 'trial', + stripeSubscriptionId, + }); + + const periodStart = new Date().toISOString(); + const periodEnd = new Date(Date.now() + 30 * 86_400_000).toISOString(); + const stripePaymentId = `ch_${crypto.randomUUID()}`; + + await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart, + periodEnd, + }); + expect(countSubscriptionStartedSends()).toBe(1); + + // Simulate the first run failing to send the email (marker not persisted): + // delete the email-log row, then replay with same stripe_payment_id. + await db + .delete(kiloclaw_email_log) + .where( + and( + eq(kiloclaw_email_log.user_id, user.id), + eq(kiloclaw_email_log.instance_id, instance.id), + eq(kiloclaw_email_log.email_type, KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE) + ) + ); + sendMock.mockClear(); + + await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart, + periodEnd, + }); + + expect(countSubscriptionStartedSends()).toBe(1); + expect(await countEmailLogRows(user.id, instance.id)).toBe(1); + }); + + test('stale duplicate recovery guard → old change-log row outside the window does not trigger a recovered email', async () => { + const user = await insertTestUser({}); + const stripeSubscriptionId = `sub_stale_${crypto.randomUUID()}`; + const { instance } = await seedSubscription({ + userId: user.id, + status: 'trialing', + plan: 'trial', + stripeSubscriptionId, + }); + + const periodStart = new Date().toISOString(); + const periodEnd = new Date(Date.now() + 30 * 86_400_000).toISOString(); + const stripePaymentId = `ch_${crypto.randomUUID()}`; + + await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart, + periodEnd, + }); + expect(countSubscriptionStartedSends()).toBe(1); + + // Backdate the change-log row well outside the recovery window relative + // to periodStart, and clear the email-log row. A replay must NOT send. + const backdated = new Date( + new Date(periodStart).getTime() - SUBSCRIPTION_STARTED_RECOVERY_WINDOW_MS - 86_400_000 + ).toISOString(); + await db + .update(kiloclaw_subscription_change_log) + .set({ created_at: backdated }) + .where( + and( + eq(kiloclaw_subscription_change_log.action, 'period_advanced'), + eq(kiloclaw_subscription_change_log.reason, 'stripe_invoice_settlement') + ) + ); + await db + .delete(kiloclaw_email_log) + .where( + and( + eq(kiloclaw_email_log.user_id, user.id), + eq(kiloclaw_email_log.instance_id, instance.id), + eq(kiloclaw_email_log.email_type, KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE) + ) + ); + sendMock.mockClear(); + + await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart, + periodEnd, + }); + + expect(countSubscriptionStartedSends()).toBe(0); + expect(await countEmailLogRows(user.id, instance.id)).toBe(0); + }); +}); From 0e720907de8f0280a99f03cf66b0573382d0a0cf Mon Sep 17 00:00:00 2001 From: Evan Jacobson Date: Mon, 4 May 2026 13:22:30 -0600 Subject: [PATCH 05/11] fix(emails): match kiloclaw subscription-created activation on period identity Replaces the created_at ordering used in didStripeSubscriptionCreatedRecordEligibleActivation with a direct plan + period_start + period_end identity match against the stripe_subscription_created row's after_state. created_at defaults to now() (transaction-start), which under concurrent webhook transactions can reorder relative to commit chronology and let a stale activation log re-fire the email on a later renewal when the email-log marker is absent (e.g. after the intentional rollback in maybeSendKiloClawSubscriptionStartedEmail error path). The handler in stripe-handlers.ts already stamps the Stripe-derived plan and period boundaries onto both the subscription row and the change-log after_state, so an activation log can only match the specific period it activated. A later renewal covers a different period and cannot match. Mirrors the existing identity-match approach in didPriorSettlementRecordPaidActivation. Tests updated to stamp period boundaries when simulating handleKiloClawSubscriptionCreated and to seed the prior-activation renewal case with a different period than the current settlement. --- apps/web/src/lib/kiloclaw/credit-billing.ts | 83 +++++++++++++- apps/web/src/lib/purchase-emails.test.ts | 113 ++++++++++++++++++++ 2 files changed, 195 insertions(+), 1 deletion(-) diff --git a/apps/web/src/lib/kiloclaw/credit-billing.ts b/apps/web/src/lib/kiloclaw/credit-billing.ts index 9040dc3da4..70c6d259fd 100644 --- a/apps/web/src/lib/kiloclaw/credit-billing.ts +++ b/apps/web/src/lib/kiloclaw/credit-billing.ts @@ -619,8 +619,22 @@ export async function applyStripeFundedKiloClawPeriod(params: { .from(kiloclaw_subscriptions) .where(eq(kiloclaw_subscriptions.id, targetRow.id)) .limit(1); + // Prefer the in-memory `before.status`. When Stripe's + // customer.subscription.created handler ran before invoice.paid, it + // already transitioned a non-hybrid row to 'active', hiding the + // pre-activation state from this snapshot. Fall back to the durable + // `kiloclaw_subscription_change_log` entry written by that handler, + // which preserves the pre-Stripe `before_state.status` and records the + // Stripe-derived plan/period in `after_state`. shouldSendSubscriptionStartedEmailForNewSettlement = - shouldSendSubscriptionStartedEmailForActivation(before?.status ?? null); + shouldSendSubscriptionStartedEmailForActivation(before?.status ?? null) || + (await didStripeSubscriptionCreatedRecordEligibleActivation({ + tx, + subscriptionId: targetRow.id, + plan, + periodStart, + periodEnd, + })); const [after] = await tx .update(kiloclaw_subscriptions) .set(updateSet) @@ -798,6 +812,73 @@ async function didPriorSettlementRecordPaidActivation(params: { return false; } +// Durable pre-settlement activation signal. +// +// handleKiloClawSubscriptionCreated can run before invoice.paid and will +// transition a non-hybrid row to status='active', masking the pre-Stripe +// status from the in-transaction snapshot used to decide whether this +// settlement is a first paid activation. The handler writes a +// `stripe_subscription_created` change-log row that preserves +// `before_state.status` and records the Stripe-derived plan/period in +// `after_state`, which is the durable evidence we need. +// +// Returns true when a `stripe_subscription_created` entry for this +// subscription has: +// - `before_state.status` that `shouldSendSubscriptionStartedEmailForActivation` +// accepts (trialing or canceled), AND +// - `after_state.plan` / `after_state.current_period_start` / +// `after_state.current_period_end` matching the current settlement. +// +// Matching on identity (plan + period boundaries) instead of audit-log +// ordering avoids relying on `created_at`, which is `now()` and therefore +// transaction-start scoped rather than a reliable commit/insert chronology +// under concurrent webhook transactions. A later renewal settlement has a +// different period than the original activation, so an old +// `stripe_subscription_created` row from the initial activation cannot match +// and cannot re-fire the email. The `kiloclaw_email_log` unique index +// remains the final idempotency guard. +async function didStripeSubscriptionCreatedRecordEligibleActivation(params: { + tx: CreditBillingTx; + subscriptionId: string; + plan: 'commit' | 'standard'; + periodStart: string; + periodEnd: string; +}): Promise { + const { tx, subscriptionId, plan, periodStart, periodEnd } = params; + const rows = await tx + .select({ + before_state: kiloclaw_subscription_change_log.before_state, + after_state: kiloclaw_subscription_change_log.after_state, + }) + .from(kiloclaw_subscription_change_log) + .where( + and( + eq(kiloclaw_subscription_change_log.subscription_id, subscriptionId), + eq(kiloclaw_subscription_change_log.reason, 'stripe_subscription_created') + ) + ) + .orderBy(desc(kiloclaw_subscription_change_log.created_at)) + .limit(20); + + for (const row of rows) { + if (!isRecord(row.before_state) || !isRecord(row.after_state)) continue; + const beforeStatus = stringFieldOrNull(row.before_state, 'status'); + if (!shouldSendSubscriptionStartedEmailForActivation(beforeStatus)) continue; + const afterPlan = stringFieldOrNull(row.after_state, 'plan'); + const afterPeriodStart = stringFieldOrNull(row.after_state, 'current_period_start'); + const afterPeriodEnd = stringFieldOrNull(row.after_state, 'current_period_end'); + if ( + afterPlan === plan && + timestampsEqual(afterPeriodStart, periodStart) && + timestampsEqual(afterPeriodEnd, periodEnd) + ) { + return true; + } + } + + return false; +} + function formatBillingPeriod(periodStart: string, periodEnd: string): string { const start = format(new Date(periodStart), 'MMM d, yyyy'); const end = format(new Date(periodEnd), 'MMM d, yyyy'); diff --git a/apps/web/src/lib/purchase-emails.test.ts b/apps/web/src/lib/purchase-emails.test.ts index f7bf484f5a..0759db623b 100644 --- a/apps/web/src/lib/purchase-emails.test.ts +++ b/apps/web/src/lib/purchase-emails.test.ts @@ -6,6 +6,7 @@ import { kiloclaw_subscription_change_log, kiloclaw_subscriptions, } from '@kilocode/db/schema'; +import { insertKiloClawSubscriptionChangeLog } from '@kilocode/db'; import { db } from '@/lib/drizzle'; import { insertTestUser } from '@/tests/helpers/user.helper'; import { processTopUp } from '@/lib/credits'; @@ -463,6 +464,65 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { expect(await countEmailLogRows(user.id, instance.id)).toBe(1); }); + test('subscription.created before invoice.paid → settlement still sends one subscription-started email', async () => { + // Realistic Stripe ordering: customer.subscription.created is processed + // before invoice.paid. handleKiloClawSubscriptionCreated flips a non-hybrid + // row to status='active', stamps the Stripe-derived period boundaries onto + // the row, and writes a durable `stripe_subscription_created` change-log + // row preserving the pre-Stripe status. The subsequent settlement's + // in-memory `before.status` is already 'active', so the email decision + // must fall back to the durable log. + const user = await insertTestUser({}); + const stripeSubscriptionId = `sub_created_before_paid_${crypto.randomUUID()}`; + const { instance, subscription } = await seedSubscription({ + userId: user.id, + status: 'trialing', + plan: 'trial', + stripeSubscriptionId, + }); + + const periodStart = new Date().toISOString(); + const periodEnd = new Date(Date.now() + 30 * 86_400_000).toISOString(); + + const trialingSnapshot = subscription; + // Simulate handleKiloClawSubscriptionCreated running before invoice.paid + // (see apps/web/src/lib/kiloclaw/stripe-handlers.ts): for non-hybrid rows + // it stamps the Stripe-derived plan, status, and period boundaries. + const [activatedSubscription] = await db + .update(kiloclaw_subscriptions) + .set({ + status: 'active', + plan: 'standard', + current_period_start: periodStart, + current_period_end: periodEnd, + }) + .where(eq(kiloclaw_subscriptions.id, subscription.id)) + .returning(); + await insertKiloClawSubscriptionChangeLog(db, { + subscriptionId: subscription.id, + actor: { actorType: 'system', actorId: 'stripe-webhook' }, + action: 'status_changed', + reason: 'stripe_subscription_created', + before: trialingSnapshot, + after: activatedSubscription, + }); + + const applied = await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId: `ch_${crypto.randomUUID()}`, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart, + periodEnd, + }); + + expect(applied).toBe(true); + expect(countSubscriptionStartedSends()).toBe(1); + expect(await countEmailLogRows(user.id, instance.id)).toBe(1); + }); + test('active renewal → no subscription-started email', async () => { const user = await insertTestUser({}); const stripeSubscriptionId = `sub_renewal_${crypto.randomUUID()}`; @@ -489,6 +549,59 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { expect(await countEmailLogRows(user.id, instance.id)).toBe(0); }); + test('active renewal after a prior activation → eligible subscription.created log for a different period does NOT trigger a second email', async () => { + // Defence-in-depth for the durable-signal fallback: the helper matches on + // plan + period boundaries of the `stripe_subscription_created.after_state` + // against the current settlement period, so an activation log recorded for + // the original (earlier) period cannot re-fire the email on subsequent + // renewal settlements that cover a different period. + const user = await insertTestUser({}); + const stripeSubscriptionId = `sub_renewal_after_prior_${crypto.randomUUID()}`; + const { instance, subscription } = await seedSubscription({ + userId: user.id, + status: 'active', + plan: 'standard', + stripeSubscriptionId, + }); + + // Original stripe_subscription_created (trialing → active) from activation. + // `subscription.current_period_start/end` are seeded to the prior period + // (30 days ago → 1 day ago), which is deliberately different from the + // renewal settlement period used below. + await insertKiloClawSubscriptionChangeLog(db, { + subscriptionId: subscription.id, + actor: { actorType: 'system', actorId: 'stripe-webhook' }, + action: 'status_changed', + reason: 'stripe_subscription_created', + before: { ...subscription, status: 'trialing' }, + after: subscription, + }); + // Prior settlement that already handled the activation email. + await insertKiloClawSubscriptionChangeLog(db, { + subscriptionId: subscription.id, + actor: { actorType: 'system', actorId: 'kiloclaw-credit-billing' }, + action: 'period_advanced', + reason: 'stripe_invoice_settlement', + before: { ...subscription, status: 'trialing' }, + after: subscription, + }); + + const applied = await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId: `ch_${crypto.randomUUID()}`, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart: new Date().toISOString(), + periodEnd: new Date(Date.now() + 30 * 86_400_000).toISOString(), + }); + + expect(applied).toBe(true); + expect(countSubscriptionStartedSends()).toBe(0); + expect(await countEmailLogRows(user.id, instance.id)).toBe(0); + }); + test('duplicate webhook replay → no second email when the log row already exists', async () => { const user = await insertTestUser({}); const stripeSubscriptionId = `sub_replay_${crypto.randomUUID()}`; From ef66051b644e4268e74e1e465ef06cacaa480b7a Mon Sep 17 00:00:00 2001 From: Evan Jacobson Date: Mon, 4 May 2026 13:23:11 -0600 Subject: [PATCH 06/11] test(emails): scope stale-recovery subscription_change_log update by subscription_id The 'stale duplicate recovery guard' test backdated every matching period_advanced / stripe_invoice_settlement row without scoping to the test's subscription, mutating shared DB state from earlier tests in the file and potentially corrupting later assertions. seedSubscription already returns the subscription row; destructure it and add eq(kiloclaw_subscription_change_log.subscription_id, subscription.id) to the WHERE clause alongside the existing action / reason predicates. --- apps/web/src/lib/purchase-emails.test.ts | 3 ++- 1 file changed, 2 insertions(+), 1 deletion(-) diff --git a/apps/web/src/lib/purchase-emails.test.ts b/apps/web/src/lib/purchase-emails.test.ts index 0759db623b..966f36ed64 100644 --- a/apps/web/src/lib/purchase-emails.test.ts +++ b/apps/web/src/lib/purchase-emails.test.ts @@ -705,7 +705,7 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { test('stale duplicate recovery guard → old change-log row outside the window does not trigger a recovered email', async () => { const user = await insertTestUser({}); const stripeSubscriptionId = `sub_stale_${crypto.randomUUID()}`; - const { instance } = await seedSubscription({ + const { instance, subscription } = await seedSubscription({ userId: user.id, status: 'trialing', plan: 'trial', @@ -738,6 +738,7 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { .set({ created_at: backdated }) .where( and( + eq(kiloclaw_subscription_change_log.subscription_id, subscription.id), eq(kiloclaw_subscription_change_log.action, 'period_advanced'), eq(kiloclaw_subscription_change_log.reason, 'stripe_invoice_settlement') ) From e66a6acd0d1cd009ac42e3a1851990e71583bf38 Mon Sep 17 00:00:00 2001 From: Evan Jacobson Date: Mon, 4 May 2026 13:53:22 -0600 Subject: [PATCH 07/11] fix(emails): dedupe kiloclaw subscription-started email by activation period MIME-Version: 1.0 Content-Type: text/plain; charset=UTF-8 Content-Transfer-Encoding: 8bit ## What changed Replaces the per-instance-lifetime idempotency key on `kiloclaw_email_log` with a per-activation key so that users who cancel and resubscribe on the same KiloClaw instance actually receive a second subscription-started email. - `packages/db/src/schema.ts` + migration `0106_noisy_pete_wisdom.sql`: add `period_start timestamptz NOT NULL DEFAULT 'epoch'` to `kiloclaw_email_log`; drop `UQ_kiloclaw_email_log_user_instance_type`; add `UQ_kiloclaw_email_log_user_instance_type_period` on `(user_id, instance_id, email_type, period_start)` WHERE `instance_id IS NOT NULL`. - `apps/web/src/lib/kiloclaw/credit-billing.ts`: the insert-before-send in `maybeSendKiloClawSubscriptionStartedEmail` now writes `period_start`, and the delete-on-error branch now scopes by `period_start` so a failed send only clears its own marker. - `apps/web/src/lib/purchase-emails.test.ts`: rewrote the unique-index unit test for the new shape, added a sibling test proving the index admits a second row for a new period, and added an end-to-end regression test that activates, cancels, and resubscribes on the same instance and asserts two sends and two log rows. ## Why this matters The KiloClaw transactional email work introduced a subscription-started email gated on `kiloclaw_email_log` as the durable idempotency surface. The existing unique index on `(user_id, instance_id, email_type)` was designed for one-per-instance-lifetime emails (e.g. `claw_instance_ready`) and is wrong for activation-event emails: after the first activation wrote a row, every future resubscribe on the same instance would conflict on the index, `onConflictDoNothing` would return `rowCount=0`, and the function would exit early without sending. Users who cancel and rejoin — a normal lifecycle — silently lost their activation email. The adversarial review captured this as cloud-ib7 with the explicit instruction to pick one of two product semantics and make the code consistent with the test expectation. We picked "one email per activation event" because (a) the existing test at purchase-emails.test.ts:440 already asserts a canceled-paid resubscribe should send, and (b) removing canceled-paid rows from eligibility would deprive returning customers of a confirmation they reasonably expect. ## Decisions **Why a `period_start` column and not a `subscription_id` column.** Resubscribe (both Stripe checkout and credit enrollment) UPDATEs the existing `kiloclaw_subscriptions` row in place rather than inserting a new one — Stripe path at `stripe-handlers.ts:870+` (allowed when `existingRow.status === 'canceled'`), credit path at `credit-billing.ts:1147` via `onConflictDoUpdate` on `instance_id`. Our internal `kiloclaw_subscriptions.id` is therefore stable across every activation on the instance and adds no discriminative power as a dedupe key. `stripe_subscription_id` is NULL for pure-credit subscriptions (`enrollWithCredits` explicitly writes `stripe_subscription_id: null`), so it cannot serve as the key either without special-casing. What actually differs across activations on both paths is the period boundary: Stripe stamps fresh `current_period_start` from the invoice line item; credits stamp `nowIso` on every enrollment. One column handles both paths. **Why `NOT NULL DEFAULT 'epoch'` instead of nullable.** Postgres treats `NULL` as distinct in unique indexes by default, which would let any other email type that omits `period_start` insert multiple rows and break the existing one-per-instance-lifetime contract for `claw_instance_ready`, `claw_suspended_*`, and friends. Drizzle's `nullsNotDistinct()` is only available on `unique()` constraints, which do not support partial `WHERE`. Defaulting to `'epoch'` lets every existing writer keep working unchanged — they all collapse onto the same `(user, instance, type, 'epoch')` index row — while only the subscription-started email path opts in to per-activation keying by explicitly writing `periodStart`. **Why not a synthetic `dedupe_key text`.** A natural timestamp column is queryable, self-documenting, and makes admin tooling easier ("show me all activation emails for period X"). A synthetic string key forces every reader to parse it. **Why the delete-on-error also got tightened.** The previous delete cleared every row for `(user, instance, type)`, which was fine when only one row could exist. With per-activation keying it would be a foot-gun: a failed send on activation N could erase activation N-1's durable marker. The new scope is `(user, instance, type, periodStart)` so a failure only touches its own insert. ## Impact and side effects **Other writers of `kiloclaw_email_log` are unaffected.** The kiloclaw billing worker (`services/kiloclaw-billing/src/lifecycle.ts`), the KiloClaw router instance-destroy cleanup, the admin trial-reset flow, and the admin instance-reset flow all write and delete rows without referencing `period_start`. The `DEFAULT 'epoch'` fills in a stable value so their inserts still collapse one-per-(user, instance, type) and their deletes (filtered by `email_type IN (...)`) still match every relevant row regardless of `period_start`. **Existing production rows get `period_start='epoch'` on backfill.** For `kiloclaw_subscription_started` rows written before the migration, this means the first post-deploy activation on the same instance will write a row with a real `periodStart` and succeed. For renewals that is correctly suppressed upstream by `shouldSendSubscriptionStartedEmailForActivation` (before we ever reach the email helper), so existing active subscribers do not get duplicate emails. For resubscribes — the exact cohort this fix exists for — a second email correctly fires. **Coordinates with adjacent beads.** - cloud-4lb (enrollWithCredits does not send subscription-started on credit activation) becomes trivial to land: pass the new period start to `maybeSendKiloClawSubscriptionStartedEmail` and per-activation dedupe already works for the credit path. - cloud-j1o (template copy hard-codes "first billing period") was previously moot because resubscribes never received the email. It is now a real product bug and should be addressed. **Does not touch.** Email rendering or templates, credit accounting, Stripe webhook parsing, subscription lifecycle state machine, top-up email flow (cloud-0zq), `softDeleteUser`/GDPR retention (the new column is a billing-period boundary, not PII; the retention test at `user.test.ts:1536` still passes). ## Verification Manually verified: - `pnpm --filter web typecheck` passes - `pnpm --filter kiloclaw-billing typecheck` passes - `pnpm --filter web test -- purchase-emails` — 20/20 pass, including the new per-period admit-second-row test and the end-to-end activate→cancel→resubscribe test - `pnpm --filter web test -- user.test` — 59/59 pass, including the GDPR retention test - `pnpm --filter kiloclaw-billing test` — 60/60 pass - `pnpm format` clean Closes cloud-ib7. --- apps/web/src/lib/kiloclaw/credit-billing.ts | 19 +- apps/web/src/lib/purchase-emails.test.ts | 119 +- .../src/migrations/0106_noisy_pete_wisdom.sql | 3 + .../db/src/migrations/meta/0106_snapshot.json | 17976 ++++++++++++++++ packages/db/src/migrations/meta/_journal.json | 7 + packages/db/src/schema.ts | 15 +- 6 files changed, 18129 insertions(+), 10 deletions(-) create mode 100644 packages/db/src/migrations/0106_noisy_pete_wisdom.sql create mode 100644 packages/db/src/migrations/meta/0106_snapshot.json diff --git a/apps/web/src/lib/kiloclaw/credit-billing.ts b/apps/web/src/lib/kiloclaw/credit-billing.ts index 70c6d259fd..5daa403da7 100644 --- a/apps/web/src/lib/kiloclaw/credit-billing.ts +++ b/apps/web/src/lib/kiloclaw/credit-billing.ts @@ -890,8 +890,13 @@ function planDisplayName(plan: 'commit' | 'standard'): string { } // Idempotency: insert-before-send on `kiloclaw_email_log` guarded by the -// unique index (user_id, instance_id, email_type). Only the first paid period -// inserts a row; renewals (which would attempt the same row) are skipped. +// unique index (user_id, instance_id, email_type, period_start). Each +// activation event (fresh `periodStart`) gets exactly one row; webhook +// replays of the same event collide on the index and return early. Because +// the KiloClaw subscription row is reused across cancel+resubscribe (both +// Stripe and credit paths UPDATE in place), period_start is what actually +// distinguishes a resubscribe's activation from the original — hence one +// email per activation, not one per instance lifetime. async function maybeSendKiloClawSubscriptionStartedEmail(params: { userId: string; instanceId: string; @@ -908,11 +913,12 @@ async function maybeSendKiloClawSubscriptionStartedEmail(params: { user_id: userId, instance_id: instanceId, email_type: KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE, + period_start: periodStart, }) .onConflictDoNothing(); if ((insertResult.rowCount ?? 0) === 0) { - // Not the first paid period — renewal, nothing to send. + // This activation was already processed — webhook replay, nothing to send. return; } @@ -944,7 +950,9 @@ async function maybeSendKiloClawSubscriptionStartedEmail(params: { extra: { user_id: userId, instance_id: instanceId, plan }, }); // Best-effort rollback so a retry can re-attempt — mirrors the pattern in - // apps/web/src/app/api/internal/kiloclaw/instance-ready/route.ts. + // apps/web/src/app/api/internal/kiloclaw/instance-ready/route.ts. Scope + // the delete to this activation's period so we only clear the marker we + // just inserted. try { await db .delete(kiloclaw_email_log) @@ -952,7 +960,8 @@ async function maybeSendKiloClawSubscriptionStartedEmail(params: { and( eq(kiloclaw_email_log.user_id, userId), eq(kiloclaw_email_log.instance_id, instanceId), - eq(kiloclaw_email_log.email_type, KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE) + eq(kiloclaw_email_log.email_type, KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE), + eq(kiloclaw_email_log.period_start, periodStart) ) ); } catch { diff --git a/apps/web/src/lib/purchase-emails.test.ts b/apps/web/src/lib/purchase-emails.test.ts index 966f36ed64..eb940e5edc 100644 --- a/apps/web/src/lib/purchase-emails.test.ts +++ b/apps/web/src/lib/purchase-emails.test.ts @@ -264,9 +264,10 @@ describe('KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE constant', () => { expect(KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE).toBe('kiloclaw_subscription_started'); }); - test('kiloclaw_email_log unique index prevents duplicate inserts for (user, instance, type)', async () => { - // Production code writes (user_id, instance_id, email_type) via the - // per-instance unique index, so test that exact shape here. + test('kiloclaw_email_log unique index dedupes webhook replays of the same activation', async () => { + // Production code writes (user_id, instance_id, email_type, period_start) + // via the per-instance/period unique index. A second insert with the same + // period_start collides (webhook replay). const user = await insertTestUser({}); const [instance] = await db .insert(kiloclaw_instances) @@ -276,12 +277,14 @@ describe('KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE constant', () => { }) .returning(); + const periodStart = new Date().toISOString(); const first = await db .insert(kiloclaw_email_log) .values({ user_id: user.id, instance_id: instance.id, email_type: KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE, + period_start: periodStart, }) .onConflictDoNothing(); expect(first.rowCount).toBe(1); @@ -292,6 +295,7 @@ describe('KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE constant', () => { user_id: user.id, instance_id: instance.id, email_type: KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE, + period_start: periodStart, }) .onConflictDoNothing(); expect(second.rowCount).toBe(0); @@ -308,6 +312,57 @@ describe('KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE constant', () => { ); expect(rows).toHaveLength(1); }); + + test('kiloclaw_email_log unique index allows a second row for a new activation period', async () => { + // Cancel+resubscribe reuses the same kiloclaw_subscriptions row but + // stamps a fresh current_period_start, so the per-activation unique + // index admits a second row and a second email goes out. + const user = await insertTestUser({}); + const [instance] = await db + .insert(kiloclaw_instances) + .values({ + user_id: user.id, + sandbox_id: `test-sandbox-${crypto.randomUUID()}`, + }) + .returning(); + + const firstPeriodStart = new Date(Date.now() - 30 * 86_400_000).toISOString(); + const secondPeriodStart = new Date().toISOString(); + + const first = await db + .insert(kiloclaw_email_log) + .values({ + user_id: user.id, + instance_id: instance.id, + email_type: KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE, + period_start: firstPeriodStart, + }) + .onConflictDoNothing(); + expect(first.rowCount).toBe(1); + + const second = await db + .insert(kiloclaw_email_log) + .values({ + user_id: user.id, + instance_id: instance.id, + email_type: KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE, + period_start: secondPeriodStart, + }) + .onConflictDoNothing(); + expect(second.rowCount).toBe(1); + + const rows = await db + .select() + .from(kiloclaw_email_log) + .where( + and( + eq(kiloclaw_email_log.user_id, user.id), + eq(kiloclaw_email_log.instance_id, instance.id), + eq(kiloclaw_email_log.email_type, KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE) + ) + ); + expect(rows).toHaveLength(2); + }); }); // ── Stripe-funded settlement → subscription-started email ────────────────── @@ -464,6 +519,64 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { expect(await countEmailLogRows(user.id, instance.id)).toBe(1); }); + test('activate → cancel → resubscribe on same instance sends a second subscription-started email', async () => { + // Real-world flow: user activates, receives the email, cancels, then + // resubscribes later. Both paid activations on the same instance should + // each send a subscription-started email because each activation covers + // a different period. The per-instance lifetime dedupe (pre-fix) would + // suppress the second email. + const user = await insertTestUser({}); + const stripeSubscriptionId = `sub_resubscribe_${crypto.randomUUID()}`; + const { instance, subscription } = await seedSubscription({ + userId: user.id, + status: 'trialing', + plan: 'trial', + stripeSubscriptionId, + }); + + // First activation: trial → paid. + const firstPeriodStart = new Date(Date.now() - 60 * 86_400_000).toISOString(); + const firstPeriodEnd = new Date(Date.now() - 30 * 86_400_000).toISOString(); + await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId: `ch_first_${crypto.randomUUID()}`, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart: firstPeriodStart, + periodEnd: firstPeriodEnd, + }); + expect(countSubscriptionStartedSends()).toBe(1); + expect(await countEmailLogRows(user.id, instance.id)).toBe(1); + + sendMock.mockClear(); + + // Simulate cancellation: status=canceled on the same row. + await db + .update(kiloclaw_subscriptions) + .set({ status: 'canceled' }) + .where(eq(kiloclaw_subscriptions.id, subscription.id)); + + // Second activation (resubscribe): same row, fresh period boundaries. + const secondPeriodStart = new Date().toISOString(); + const secondPeriodEnd = new Date(Date.now() + 30 * 86_400_000).toISOString(); + const applied = await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId: `ch_second_${crypto.randomUUID()}`, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart: secondPeriodStart, + periodEnd: secondPeriodEnd, + }); + + expect(applied).toBe(true); + expect(countSubscriptionStartedSends()).toBe(1); + expect(await countEmailLogRows(user.id, instance.id)).toBe(2); + }); + test('subscription.created before invoice.paid → settlement still sends one subscription-started email', async () => { // Realistic Stripe ordering: customer.subscription.created is processed // before invoice.paid. handleKiloClawSubscriptionCreated flips a non-hybrid diff --git a/packages/db/src/migrations/0106_noisy_pete_wisdom.sql b/packages/db/src/migrations/0106_noisy_pete_wisdom.sql new file mode 100644 index 0000000000..726432c56b --- /dev/null +++ b/packages/db/src/migrations/0106_noisy_pete_wisdom.sql @@ -0,0 +1,3 @@ +DROP INDEX "UQ_kiloclaw_email_log_user_instance_type";--> statement-breakpoint +ALTER TABLE "kiloclaw_email_log" ADD COLUMN "period_start" timestamp with time zone DEFAULT 'epoch' NOT NULL;--> statement-breakpoint +CREATE UNIQUE INDEX "UQ_kiloclaw_email_log_user_instance_type_period" ON "kiloclaw_email_log" USING btree ("user_id","instance_id","email_type","period_start") WHERE "kiloclaw_email_log"."instance_id" is not null; \ No newline at end of file diff --git a/packages/db/src/migrations/meta/0106_snapshot.json b/packages/db/src/migrations/meta/0106_snapshot.json new file mode 100644 index 0000000000..a49b558ead --- /dev/null +++ b/packages/db/src/migrations/meta/0106_snapshot.json @@ -0,0 +1,17976 @@ +{ + "id": "9544515c-0b8d-48e4-a18d-39a81d76fbbd", + "prevId": "f9fd2e78-846d-49b9-923e-90da6e9c6d63", + "version": "7", + "dialect": "postgresql", + "tables": { + "public.agent_configs": { + "name": "agent_configs", + "schema": "", + "columns": { + "id": { + "name": "id", + "type": "uuid", + "primaryKey": true, + "notNull": true, + "default": "pg_catalog.gen_random_uuid()" + }, + "owned_by_organization_id": { + "name": "owned_by_organization_id", + "type": "uuid", + "primaryKey": false, + "notNull": false + }, + "owned_by_user_id": { + "name": "owned_by_user_id", + "type": "text", + "primaryKey": false, + "notNull": false + }, + "agent_type": { + "name": "agent_type", + "type": "text", + "primaryKey": false, + "notNull": true + }, + "platform": { + "name": "platform", + "type": "text", + "primaryKey": false, + "notNull": true + }, + "config": { + "name": "config", + "type": "jsonb", + "primaryKey": false, + "notNull": true, + "default": "'{}'::jsonb" + }, + "is_enabled": { + "name": "is_enabled", + "type": "boolean", + "primaryKey": false, + "notNull": true, + "default": true + }, + "runtime_state": { + "name": "runtime_state", + "type": "jsonb", + "primaryKey": false, + "notNull": false, + "default": "'{}'::jsonb" + }, + "created_by": { + "name": "created_by", + "type": "text", + "primaryKey": false, + "notNull": true + }, + "created_at": { + "name": "created_at", + "type": "timestamp with time zone", + "primaryKey": false, + "notNull": true, + "default": "now()" + }, + "updated_at": { + "name": "updated_at", + "type": "timestamp with time zone", + "primaryKey": false, + "notNull": true, + "default": "now()" + } + }, + "indexes": { + "IDX_agent_configs_org_id": { + "name": "IDX_agent_configs_org_id", + "columns": [ + { + "expression": "owned_by_organization_id", + "isExpression": false, + "asc": true, + "nulls": "last" + } + ], + "isUnique": false, + "concurrently": false, + "method": "btree", + "with": {} + }, + "IDX_agent_configs_owned_by_user_id": { + "name": "IDX_agent_configs_owned_by_user_id", + "columns": [ + { + "expression": "owned_by_user_id", + "isExpression": false, + "asc": true, + "nulls": "last" + } + ], + "isUnique": false, + "concurrently": false, + "method": "btree", + "with": {} + }, + "IDX_agent_configs_agent_type": { + "name": "IDX_agent_configs_agent_type", + "columns": [ + { + "expression": "agent_type", + "isExpression": false, + "asc": true, + "nulls": "last" + } + ], + "isUnique": false, + "concurrently": false, + "method": "btree", + "with": {} + }, + "IDX_agent_configs_platform": { + "name": "IDX_agent_configs_platform", + "columns": [ + { + "expression": "platform", + "isExpression": false, + "asc": true, + "nulls": "last" + } + ], + "isUnique": false, + "concurrently": false, + "method": "btree", + "with": {} + } + }, + "foreignKeys": { + "agent_configs_owned_by_organization_id_organizations_id_fk": { + "name": "agent_configs_owned_by_organization_id_organizations_id_fk", + "tableFrom": "agent_configs", + "tableTo": "organizations", + "columnsFrom": [ + "owned_by_organization_id" + ], + "columnsTo": [ + "id" + ], + "onDelete": "cascade", + "onUpdate": "no action" + }, + "agent_configs_owned_by_user_id_kilocode_users_id_fk": { + "name": "agent_configs_owned_by_user_id_kilocode_users_id_fk", + "tableFrom": "agent_configs", + "tableTo": "kilocode_users", + "columnsFrom": [ + "owned_by_user_id" + ], + "columnsTo": [ + "id" + ], + "onDelete": "cascade", + "onUpdate": "no action" + } + }, + "compositePrimaryKeys": {}, + "uniqueConstraints": { + "UQ_agent_configs_org_agent_platform": { + "name": "UQ_agent_configs_org_agent_platform", + "nullsNotDistinct": false, + "columns": [ + "owned_by_organization_id", + "agent_type", + "platform" + ] + }, + "UQ_agent_configs_user_agent_platform": { + "name": "UQ_agent_configs_user_agent_platform", + "nullsNotDistinct": false, + "columns": [ + "owned_by_user_id", + "agent_type", + "platform" + ] + } + }, + "policies": {}, + "checkConstraints": { + "agent_configs_owner_check": { + "name": "agent_configs_owner_check", + "value": "(\n (\"agent_configs\".\"owned_by_user_id\" IS NOT NULL AND \"agent_configs\".\"owned_by_organization_id\" IS NULL) OR\n (\"agent_configs\".\"owned_by_user_id\" IS NULL AND \"agent_configs\".\"owned_by_organization_id\" IS NOT NULL)\n )" + }, + "agent_configs_agent_type_check": { + "name": "agent_configs_agent_type_check", + "value": "\"agent_configs\".\"agent_type\" IN ('code_review', 'auto_triage', 'auto_fix', 'security_scan')" + } + }, + "isRLSEnabled": false + }, + "public.agent_environment_profile_commands": { + "name": "agent_environment_profile_commands", + "schema": "", + "columns": { + "id": { + "name": "id", + "type": "uuid", + "primaryKey": true, + "notNull": true, + "default": "pg_catalog.gen_random_uuid()" + }, + "profile_id": { + "name": "profile_id", + "type": "uuid", + "primaryKey": false, + "notNull": true + }, + "sequence": { + "name": "sequence", + "type": "integer", + "primaryKey": false, + "notNull": true + }, + "command": { + "name": "command", + "type": "text", + "primaryKey": false, + "notNull": true + }, + "created_at": { + "name": "created_at", + "type": "timestamp with time zone", + "primaryKey": false, + "notNull": true, + "default": "now()" + } + }, + "indexes": { + "IDX_agent_env_profile_commands_profile_id": { + "name": "IDX_agent_env_profile_commands_profile_id", + "columns": [ + { + "expression": "profile_id", + "isExpression": false, + "asc": true, + "nulls": "last" + } + ], + "isUnique": false, + "concurrently": false, + "method": "btree", + "with": {} + } + }, + "foreignKeys": { + "agent_environment_profile_commands_profile_id_agent_environment_profiles_id_fk": { + "name": "agent_environment_profile_commands_profile_id_agent_environment_profiles_id_fk", + "tableFrom": "agent_environment_profile_commands", + "tableTo": "agent_environment_profiles", + "columnsFrom": [ + "profile_id" + ], + "columnsTo": [ + "id" + ], + "onDelete": "cascade", + "onUpdate": "no action" + } + }, + "compositePrimaryKeys": {}, + "uniqueConstraints": { + "UQ_agent_env_profile_commands_profile_sequence": { + "name": "UQ_agent_env_profile_commands_profile_sequence", + "nullsNotDistinct": false, + "columns": [ + "profile_id", + "sequence" + ] + } + }, + "policies": {}, + "checkConstraints": {}, + "isRLSEnabled": false + }, + "public.agent_environment_profile_repo_bindings": { + "name": "agent_environment_profile_repo_bindings", + "schema": "", + "columns": { + "id": { + "name": "id", + "type": "uuid", + "primaryKey": true, + "notNull": true, + "default": "pg_catalog.gen_random_uuid()" + }, + "repo_full_name": { + "name": "repo_full_name", + "type": "text", + "primaryKey": false, + "notNull": true + }, + "platform": { + "name": "platform", + "type": "text", + "primaryKey": false, + "notNull": true, + "default": "'github'" + }, + "profile_id": { + "name": "profile_id", + "type": "uuid", + "primaryKey": false, + "notNull": true + }, + "owned_by_organization_id": { + "name": "owned_by_organization_id", + "type": "uuid", + "primaryKey": false, + "notNull": false + }, + "owned_by_user_id": { + "name": "owned_by_user_id", + "type": "text", + "primaryKey": false, + "notNull": false + }, + "created_at": { + "name": "created_at", + "type": "timestamp with time zone", + "primaryKey": false, + "notNull": true, + "default": "now()" + } + }, + "indexes": { + "UQ_agent_env_profile_repo_bindings_user": { + "name": "UQ_agent_env_profile_repo_bindings_user", + "columns": [ + { + "expression": "repo_full_name", + "isExpression": false, + "asc": true, + "nulls": "last" + }, + { + "expression": "platform", + "isExpression": false, + "asc": true, + "nulls": "last" + }, + { + "expression": "owned_by_user_id", + "isExpression": false, + "asc": true, + "nulls": "last" + } + ], + "isUnique": true, + "where": "\"agent_environment_profile_repo_bindings\".\"owned_by_user_id\" is not null", + "concurrently": false, + "method": "btree", + "with": {} + }, + "UQ_agent_env_profile_repo_bindings_org": { + "name": "UQ_agent_env_profile_repo_bindings_org", + "columns": [ + { + "expression": "repo_full_name", + "isExpression": false, + "asc": true, + "nulls": "last" + }, + { + "expression": "platform", + "isExpression": false, + "asc": true, + "nulls": "last" + }, + { + "expression": "owned_by_organization_id", + "isExpression": false, + "asc": true, + "nulls": "last" + } + ], + "isUnique": true, + "where": "\"agent_environment_profile_repo_bindings\".\"owned_by_organization_id\" is not null", + "concurrently": false, + "method": "btree", + "with": {} + } + }, + "foreignKeys": { + "agent_environment_profile_repo_bindings_profile_id_agent_environment_profiles_id_fk": { + "name": "agent_environment_profile_repo_bindings_profile_id_agent_environment_profiles_id_fk", + "tableFrom": "agent_environment_profile_repo_bindings", + "tableTo": "agent_environment_profiles", + "columnsFrom": [ + "profile_id" + ], + "columnsTo": [ + "id" + ], + "onDelete": "cascade", + "onUpdate": "no action" + }, + "agent_environment_profile_repo_bindings_owned_by_organization_id_organizations_id_fk": { + "name": "agent_environment_profile_repo_bindings_owned_by_organization_id_organizations_id_fk", + "tableFrom": "agent_environment_profile_repo_bindings", + "tableTo": "organizations", + "columnsFrom": [ + "owned_by_organization_id" + ], + "columnsTo": [ + "id" + ], + "onDelete": "cascade", + "onUpdate": "no action" + }, + "agent_environment_profile_repo_bindings_owned_by_user_id_kilocode_users_id_fk": { + "name": "agent_environment_profile_repo_bindings_owned_by_user_id_kilocode_users_id_fk", + "tableFrom": "agent_environment_profile_repo_bindings", + "tableTo": "kilocode_users", + "columnsFrom": [ + "owned_by_user_id" + ], + "columnsTo": [ + "id" + ], + "onDelete": "cascade", + "onUpdate": "no action" + } + }, + "compositePrimaryKeys": {}, + "uniqueConstraints": {}, + "policies": {}, + "checkConstraints": { + "agent_env_profile_repo_bindings_owner_check": { + "name": "agent_env_profile_repo_bindings_owner_check", + "value": "(\n (\"agent_environment_profile_repo_bindings\".\"owned_by_user_id\" IS NOT NULL AND \"agent_environment_profile_repo_bindings\".\"owned_by_organization_id\" IS NULL) OR\n (\"agent_environment_profile_repo_bindings\".\"owned_by_user_id\" IS NULL AND \"agent_environment_profile_repo_bindings\".\"owned_by_organization_id\" IS NOT NULL)\n )" + } + }, + "isRLSEnabled": false + }, + "public.agent_environment_profile_vars": { + "name": "agent_environment_profile_vars", + "schema": "", + "columns": { + "id": { + "name": "id", + "type": "uuid", + "primaryKey": true, + "notNull": true, + "default": "pg_catalog.gen_random_uuid()" + }, + 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false + }, + "finish_reason": { + "name": "finish_reason", + "type": "text", + "primaryKey": false, + "notNull": false + }, + "latency": { + "name": "latency", + "type": "real", + "primaryKey": false, + "notNull": false + }, + "moderation_latency": { + "name": "moderation_latency", + "type": "real", + "primaryKey": false, + "notNull": false + }, + "generation_time": { + "name": "generation_time", + "type": "real", + "primaryKey": false, + "notNull": false + }, + "is_byok": { + "name": "is_byok", + "type": "boolean", + "primaryKey": false, + "notNull": false + }, + "is_user_byok": { + "name": "is_user_byok", + "type": "boolean", + "primaryKey": false, + "notNull": false + }, + "streamed": { + "name": "streamed", + "type": "boolean", + "primaryKey": false, + "notNull": false + }, + "cancelled": { + "name": "cancelled", + "type": "boolean", + "primaryKey": false, + "notNull": false + }, + "editor_name": { + "name": "editor_name", + "type": "text", + "primaryKey": false, + "notNull": false + }, + "api_kind": { + "name": "api_kind", + "type": "text", + "primaryKey": false, + "notNull": false + }, + "has_tools": { + "name": "has_tools", + "type": "boolean", + "primaryKey": false, + "notNull": false + }, + "machine_id": { + "name": "machine_id", + "type": "text", + "primaryKey": false, + "notNull": false + }, + "feature": { + "name": "feature", + "type": "text", + "primaryKey": false, + "notNull": false + }, + "session_id": { + "name": "session_id", + "type": "text", + "primaryKey": false, + "notNull": false + }, + "mode": { + "name": "mode", + "type": "text", + "primaryKey": false, + "notNull": false + }, + "auto_model": { + "name": "auto_model", + "type": "text", + "primaryKey": false, + "notNull": false + }, + "market_cost": { + "name": "market_cost", + "type": "bigint", + "primaryKey": false, + "notNull": false + }, + "is_free": { + "name": "is_free", + "type": "boolean", + "primaryKey": false, + "notNull": false + } + }, + "definition": "\n SELECT\n mu.id,\n mu.kilo_user_id,\n meta.message_id,\n mu.cost,\n mu.input_tokens,\n mu.output_tokens,\n mu.cache_write_tokens,\n mu.cache_hit_tokens,\n mu.created_at,\n ip.http_ip AS http_x_forwarded_for,\n city.vercel_ip_city AS http_x_vercel_ip_city,\n country.vercel_ip_country AS http_x_vercel_ip_country,\n meta.vercel_ip_latitude AS http_x_vercel_ip_latitude,\n meta.vercel_ip_longitude AS http_x_vercel_ip_longitude,\n ja4.ja4_digest AS http_x_vercel_ja4_digest,\n mu.provider,\n mu.model,\n mu.requested_model,\n meta.user_prompt_prefix,\n spp.system_prompt_prefix,\n meta.system_prompt_length,\n ua.http_user_agent,\n mu.cache_discount,\n meta.max_tokens,\n meta.has_middle_out_transform,\n mu.has_error,\n mu.abuse_classification,\n mu.organization_id,\n mu.inference_provider,\n mu.project_id,\n meta.status_code,\n meta.upstream_id,\n frfr.finish_reason,\n meta.latency,\n meta.moderation_latency,\n meta.generation_time,\n meta.is_byok,\n meta.is_user_byok,\n meta.streamed,\n meta.cancelled,\n edit.editor_name,\n ak.api_kind,\n meta.has_tools,\n meta.machine_id,\n feat.feature,\n meta.session_id,\n md.mode,\n am.auto_model,\n meta.market_cost,\n meta.is_free\n FROM \"microdollar_usage\" mu\n LEFT JOIN \"microdollar_usage_metadata\" meta ON mu.id = meta.id\n LEFT JOIN \"http_ip\" ip ON meta.http_ip_id = ip.http_ip_id\n LEFT JOIN \"vercel_ip_city\" city ON meta.vercel_ip_city_id = city.vercel_ip_city_id\n LEFT JOIN \"vercel_ip_country\" country ON meta.vercel_ip_country_id = country.vercel_ip_country_id\n LEFT JOIN \"ja4_digest\" ja4 ON meta.ja4_digest_id = ja4.ja4_digest_id\n LEFT JOIN \"system_prompt_prefix\" spp ON meta.system_prompt_prefix_id = spp.system_prompt_prefix_id\n LEFT JOIN \"http_user_agent\" ua ON meta.http_user_agent_id = ua.http_user_agent_id\n LEFT JOIN \"finish_reason\" frfr ON meta.finish_reason_id = frfr.finish_reason_id\n LEFT JOIN \"editor_name\" edit ON meta.editor_name_id = edit.editor_name_id\n LEFT JOIN \"api_kind\" ak ON meta.api_kind_id = ak.api_kind_id\n LEFT JOIN \"feature\" feat ON meta.feature_id = feat.feature_id\n LEFT JOIN \"mode\" md ON meta.mode_id = md.mode_id\n LEFT JOIN \"auto_model\" am ON meta.auto_model_id = am.auto_model_id\n", + "name": "microdollar_usage_view", + "schema": "public", + "isExisting": false, + "materialized": false + } + }, + "_meta": { + "columns": {}, + "schemas": {}, + "tables": {} + } +} \ No newline at end of file diff --git a/packages/db/src/migrations/meta/_journal.json b/packages/db/src/migrations/meta/_journal.json index 028e34998d..8ff0332d18 100644 --- a/packages/db/src/migrations/meta/_journal.json +++ b/packages/db/src/migrations/meta/_journal.json @@ -743,6 +743,13 @@ "when": 1777032309451, "tag": "0105_married_harry_osborn", "breakpoints": true + }, + { + "idx": 106, + "version": "7", + "when": 1777923511998, + "tag": "0106_noisy_pete_wisdom", + "breakpoints": true } ] } \ No newline at end of file diff --git a/packages/db/src/schema.ts b/packages/db/src/schema.ts index 914aecb68b..a025e6f514 100644 --- a/packages/db/src/schema.ts +++ b/packages/db/src/schema.ts @@ -4155,6 +4155,14 @@ export const kiloclaw_subscription_change_log = pgTable( export type KiloClawSubscriptionChangeLog = typeof kiloclaw_subscription_change_log.$inferSelect; export type NewKiloClawSubscriptionChangeLog = typeof kiloclaw_subscription_change_log.$inferInsert; +// Per-activation dedupe for instance-scoped emails (e.g. subscription-started) +// keys on the activation's `period_start`. The owning `kiloclaw_subscriptions` +// row is reused across cancel+resubscribe (both Stripe and credit paths +// UPDATE the existing row in place), so only `period_start` — which advances +// on every fresh activation — distinguishes activation events. `period_start` +// defaults to the Unix epoch so the unique-index math works for any future +// per-instance email type that has no natural per-activation boundary: those +// callers pass no value and collapse to one row per (user, instance, type). export const kiloclaw_email_log = pgTable( 'kiloclaw_email_log', { @@ -4167,14 +4175,17 @@ export const kiloclaw_email_log = pgTable( .references(() => kilocode_users.id), instance_id: uuid().references(() => kiloclaw_instances.id), email_type: text().notNull(), + period_start: timestamp({ withTimezone: true, mode: 'string' }) + .notNull() + .default(sql`'epoch'`), sent_at: timestamp({ withTimezone: true, mode: 'string' }).defaultNow().notNull(), }, table => [ uniqueIndex('UQ_kiloclaw_email_log_user_type_global') .on(table.user_id, table.email_type) .where(isNull(table.instance_id)), - uniqueIndex('UQ_kiloclaw_email_log_user_instance_type') - .on(table.user_id, table.instance_id, table.email_type) + uniqueIndex('UQ_kiloclaw_email_log_user_instance_type_period') + .on(table.user_id, table.instance_id, table.email_type, table.period_start) .where(isNotNull(table.instance_id)), index('IDX_kiloclaw_email_log_type_sent_instance') .on(table.email_type, table.sent_at, table.instance_id, table.user_id) From 3c64daa674d32a6a960b29b5c9f772c80e135256 Mon Sep 17 00:00:00 2001 From: Evan Jacobson Date: Mon, 4 May 2026 14:25:32 -0600 Subject: [PATCH 08/11] fix(emails): send kiloclaw subscription-started email on $0 settlements Per KiloClaw billing spec (Stripe-Funded Credit Settlement rule 10), $0 invoices must still run settlement and transition the row into the activated hybrid state. The subscription-started email is an activation notification, not a revenue side effect, so it must fire regardless of invoice amount. Revenue side effects (analytics, affiliate sale events) apply their own amount_paid > 0 guard in stripe-handlers.ts. Drops the amountMicrodollars > 0 gate on the email so users activated by a full coupon or promo still receive the activation notification. The existing '$0 Stripe settlement' test in purchase-emails.test.ts locks in this behavior. --- apps/web/src/lib/kiloclaw/credit-billing.ts | 9 ++++++++- 1 file changed, 8 insertions(+), 1 deletion(-) diff --git a/apps/web/src/lib/kiloclaw/credit-billing.ts b/apps/web/src/lib/kiloclaw/credit-billing.ts index 5daa403da7..f5a2c8d037 100644 --- a/apps/web/src/lib/kiloclaw/credit-billing.ts +++ b/apps/web/src/lib/kiloclaw/credit-billing.ts @@ -686,7 +686,14 @@ export async function applyStripeFundedKiloClawPeriod(params: { periodEnd, }))); - if (resolvedInstanceId && amountMicrodollars > 0 && shouldSendSubscriptionStartedEmail) { + // Per KiloClaw billing spec (Stripe-Funded Credit Settlement rule 10), + // $0 KiloClaw invoices must still run settlement and transition the row + // into the activated hybrid state. The subscription-started email is an + // activation notification, not a revenue side effect, so it must fire + // regardless of invoice amount. Revenue side effects (analytics, + // affiliate sale events) apply their own `amount_paid > 0` guard in + // stripe-handlers.ts. + if (resolvedInstanceId && shouldSendSubscriptionStartedEmail) { await maybeSendKiloClawSubscriptionStartedEmail({ userId, instanceId: resolvedInstanceId, From 18ce2ddf788a55166714dda78c652910f4cd8163 Mon Sep 17 00:00:00 2001 From: Evan Jacobson Date: Mon, 4 May 2026 14:25:43 -0600 Subject: [PATCH 09/11] fix(emails): clear kiloclaw subscription-started email log when provider not configured MIME-Version: 1.0 Content-Type: text/plain; charset=UTF-8 Content-Transfer-Encoding: 8bit maybeSendKiloClawSubscriptionStartedEmail inserted the kiloclaw_email_log marker before calling sendKiloClawSubscriptionStartedEmail and only deleted it if the send threw. When the provider returned {sent: false, reason: 'provider_not_configured'} without throwing (e.g. Mailgun env missing in a preview environment), the marker persisted and permanently suppressed the email on future webhook retries via the unique index guard. Inspect the SendResult and clear the marker on provider_not_configured so a retry can re-attempt. Mirrors the proven pattern in services/kiloclaw-billing/src/lifecycle.ts:879-884. neverbounce_rejected is deliberately left in place: the verdict is terminal for that address (invalid / disposable), so retrying would loop forever. Leaving the row keeps the outcome idempotent — we tried once, the address was rejected, we do not try again. Refactored the delete branch into deleteSubscriptionStartedEmailLog, reused by both the non-throwing failure path and the existing catch. Tests: one asserting the log row is cleared on provider_not_configured so a retry can re-send, one asserting the row persists on neverbounce_rejected so we do not retry a terminally invalid address. Widened sendMock's return type to SendResult so mockImplementationOnce can return {sent: false, reason: ...}. --- apps/web/src/lib/kiloclaw/credit-billing.ts | 45 ++++++-- apps/web/src/lib/purchase-emails.test.ts | 120 +++++++++++++++++++- 2 files changed, 153 insertions(+), 12 deletions(-) diff --git a/apps/web/src/lib/kiloclaw/credit-billing.ts b/apps/web/src/lib/kiloclaw/credit-billing.ts index f5a2c8d037..2e12bd49c8 100644 --- a/apps/web/src/lib/kiloclaw/credit-billing.ts +++ b/apps/web/src/lib/kiloclaw/credit-billing.ts @@ -943,13 +943,27 @@ async function maybeSendKiloClawSubscriptionStartedEmail(params: { return; } - await sendKiloClawSubscriptionStartedEmail({ + const sendResult = await sendKiloClawSubscriptionStartedEmail({ to: user.email, planName: planDisplayName(plan), priceCents: amountCents, billingPeriod: formatBillingPeriod(periodStart, periodEnd), nextBillingDate: new Date(periodEnd), }); + + // If the provider is not configured (e.g. Mailgun env missing in a test or + // preview environment), the send never reached a real provider and a later + // webhook retry should be free to re-attempt. Clear the marker we just + // inserted so the unique-index guard does not permanently suppress the + // email. Mirrors services/kiloclaw-billing/src/lifecycle.ts:879-884. + // + // `neverbounce_rejected` is deliberately NOT cleared: NeverBounce's verdict + // is terminal for that address (invalid / disposable), so retrying would + // loop forever. Leaving the row keeps the behavior idempotent — we tried + // once, the address was rejected, we don't try again. + if (!sendResult.sent && sendResult.reason === 'provider_not_configured') { + await deleteSubscriptionStartedEmailLog({ userId, instanceId, periodStart }); + } } catch (error) { // Never fail the settlement flow because of an email error. captureException(error, { @@ -961,22 +975,31 @@ async function maybeSendKiloClawSubscriptionStartedEmail(params: { // the delete to this activation's period so we only clear the marker we // just inserted. try { - await db - .delete(kiloclaw_email_log) - .where( - and( - eq(kiloclaw_email_log.user_id, userId), - eq(kiloclaw_email_log.instance_id, instanceId), - eq(kiloclaw_email_log.email_type, KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE), - eq(kiloclaw_email_log.period_start, periodStart) - ) - ); + await deleteSubscriptionStartedEmailLog({ userId, instanceId, periodStart }); } catch { // Leave the marker in place; we prefer missing one email over duplicate sends. } } } +async function deleteSubscriptionStartedEmailLog(params: { + userId: string; + instanceId: string; + periodStart: string; +}): Promise { + const { userId, instanceId, periodStart } = params; + await db + .delete(kiloclaw_email_log) + .where( + and( + eq(kiloclaw_email_log.user_id, userId), + eq(kiloclaw_email_log.instance_id, instanceId), + eq(kiloclaw_email_log.email_type, KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE), + eq(kiloclaw_email_log.period_start, periodStart) + ) + ); +} + /** * Enroll a user's instance in a KiloClaw hosting plan funded by credits. * diff --git a/apps/web/src/lib/purchase-emails.test.ts b/apps/web/src/lib/purchase-emails.test.ts index eb940e5edc..084218a8ef 100644 --- a/apps/web/src/lib/purchase-emails.test.ts +++ b/apps/web/src/lib/purchase-emails.test.ts @@ -32,7 +32,9 @@ jest.mock('@/lib/firstTopupBonus', () => ({ // The helpers are replaced with jest.fns that forward the call via // sendMock using a synthetic `templateName` so existing tests that filter // by templateName continue to work. -const sendMock = jest.fn(async (_params: unknown) => ({ sent: true as const })); +const sendMock = jest.fn, [unknown]>(async () => ({ + sent: true, +})); jest.mock('@/lib/email', () => { const actual = jest.requireActual('@/lib/email'); @@ -519,6 +521,42 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { expect(await countEmailLogRows(user.id, instance.id)).toBe(1); }); + test('$0 Stripe settlement (full coupon / promo) still sends one subscription-started email', async () => { + // Per KiloClaw billing spec Stripe-Funded Credit Settlement rule 10, + // `$0` KiloClaw invoices must still run settlement so Stripe-created + // subscriptions transition into the activated hybrid state. The + // subscription-started email is an activation notification, not a + // revenue side effect, so it must fire even when amount_paid is 0. + const user = await insertTestUser({}); + const stripeSubscriptionId = `sub_zero_amount_${crypto.randomUUID()}`; + const { instance } = await seedSubscription({ + userId: user.id, + status: 'trialing', + plan: 'trial', + stripeSubscriptionId, + }); + + const applied = await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId: `in_${crypto.randomUUID()}`, + plan: 'standard', + amountMicrodollars: 0, + periodStart: new Date().toISOString(), + periodEnd: new Date(Date.now() + 30 * 86_400_000).toISOString(), + }); + + expect(applied).toBe(true); + expect(countSubscriptionStartedSends()).toBe(1); + expect(await countEmailLogRows(user.id, instance.id)).toBe(1); + + const zeroAmountSend = sendMock.mock.calls + .map(([params]) => params as { templateName: string; templateVars: Record }) + .find(p => p.templateName === 'kiloClawSubscriptionStarted'); + expect(zeroAmountSend?.templateVars.price_usd).toBe('0.00'); + }); + test('activate → cancel → resubscribe on same instance sends a second subscription-started email', async () => { // Real-world flow: user activates, receives the email, cancels, then // resubscribes later. Both paid activations on the same instance should @@ -815,6 +853,86 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { expect(await countEmailLogRows(user.id, instance.id)).toBe(1); }); + test('provider_not_configured → email log row is cleared so a retry can re-attempt', async () => { + // Regression: maybeSendKiloClawSubscriptionStartedEmail used to insert the + // kiloclaw_email_log marker before calling the provider, and only delete + // it if the send threw. When the provider returned {sent: false, + // reason: 'provider_not_configured'} without throwing, the marker + // remained and permanently suppressed the email on future retries. + const user = await insertTestUser({}); + const stripeSubscriptionId = `sub_provider_unconfigured_${crypto.randomUUID()}`; + const { instance } = await seedSubscription({ + userId: user.id, + status: 'trialing', + plan: 'trial', + stripeSubscriptionId, + }); + + sendMock.mockImplementationOnce(async () => ({ + sent: false, + reason: 'provider_not_configured' as const, + })); + + const periodStart = new Date().toISOString(); + const periodEnd = new Date(Date.now() + 30 * 86_400_000).toISOString(); + + const applied = await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId: `ch_${crypto.randomUUID()}`, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart, + periodEnd, + }); + + expect(applied).toBe(true); + // We did attempt to send exactly once, but the provider wasn't configured. + expect(countSubscriptionStartedSends()).toBe(1); + // The marker row must be gone so a later retry can re-attempt — the + // unique index would otherwise permanently suppress this activation. + expect(await countEmailLogRows(user.id, instance.id)).toBe(0); + }); + + test('neverbounce_rejected → email log row is retained so we do not retry a terminally invalid address', async () => { + // NeverBounce's "invalid" / "disposable" verdict is terminal for that + // address; retrying would loop forever. Leaving the kiloclaw_email_log + // row in place makes the outcome idempotent: we tried once, the address + // was rejected, we don't try again. + const user = await insertTestUser({}); + const stripeSubscriptionId = `sub_neverbounce_rejected_${crypto.randomUUID()}`; + const { instance } = await seedSubscription({ + userId: user.id, + status: 'trialing', + plan: 'trial', + stripeSubscriptionId, + }); + + sendMock.mockImplementationOnce(async () => ({ + sent: false, + reason: 'neverbounce_rejected' as const, + })); + + const periodStart = new Date().toISOString(); + const periodEnd = new Date(Date.now() + 30 * 86_400_000).toISOString(); + + const applied = await applyStripeFundedKiloClawPeriod({ + userId: user.id, + metadataInstanceId: instance.id, + stripeSubscriptionId, + stripePaymentId: `ch_${crypto.randomUUID()}`, + plan: 'standard', + amountMicrodollars: 9_000_000, + periodStart, + periodEnd, + }); + + expect(applied).toBe(true); + expect(countSubscriptionStartedSends()).toBe(1); + expect(await countEmailLogRows(user.id, instance.id)).toBe(1); + }); + test('stale duplicate recovery guard → old change-log row outside the window does not trigger a recovered email', async () => { const user = await insertTestUser({}); const stripeSubscriptionId = `sub_stale_${crypto.randomUUID()}`; From c3c1ef4495a0bb1e560d560f39f5a6bd8fd78e5b Mon Sep 17 00:00:00 2001 From: Evan Jacobson Date: Mon, 4 May 2026 14:28:11 -0600 Subject: [PATCH 10/11] chore(emails): replace import() type annotation with top-level type import in purchase-emails test oxlint's consistent-type-imports rule forbids inline import() type annotations. Convert to a top-level 'import type * as creditBillingModule' at the file header, matching the existing pattern used for emailModule. --- apps/web/src/lib/purchase-emails.test.ts | 5 ++--- 1 file changed, 2 insertions(+), 3 deletions(-) diff --git a/apps/web/src/lib/purchase-emails.test.ts b/apps/web/src/lib/purchase-emails.test.ts index 084218a8ef..1306dc44cf 100644 --- a/apps/web/src/lib/purchase-emails.test.ts +++ b/apps/web/src/lib/purchase-emails.test.ts @@ -14,6 +14,7 @@ import { KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE, SUBSCRIPTION_STARTED_RECOVERY_WINDOW_MS, } from '@/lib/kiloclaw/credit-billing'; +import type * as creditBillingModule from '@/lib/kiloclaw/credit-billing'; import type * as emailModule from '@/lib/email'; import { renderTemplate, @@ -378,9 +379,7 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { }); async function applyStripeFundedKiloClawPeriod( - params: Parameters< - typeof import('@/lib/kiloclaw/credit-billing').applyStripeFundedKiloClawPeriod - >[0] + params: Parameters[0] ): Promise { const mod = await import('@/lib/kiloclaw/credit-billing'); return mod.applyStripeFundedKiloClawPeriod(params); From 0b9871164d6e7063cd2b1dc0be52408b436b07c2 Mon Sep 17 00:00:00 2001 From: Evan Jacobson Date: Mon, 4 May 2026 15:26:21 -0600 Subject: [PATCH 11/11] test(emails): mock Mailgun transport instead of helper exports MIME-Version: 1.0 Content-Type: text/plain; charset=UTF-8 Content-Transfer-Encoding: 8bit Refactors purchase-emails.test.ts to mock sendViaMailgun and verifyEmail so every test exercises the real sendCreditsTopUpEmail and sendKiloClawSubscriptionStartedEmail code paths — including formatUsd rounding, formatDate formatting, subjectOverride selection, and credits_url / manage_url / receipt_section construction. Previously the helpers themselves were mocked with synthetic implementations, so a rename like receipt_url → receipt_section would ship green. Adds direct payload tests for both helpers covering the happy path, neverbounce rejection, provider_not_configured, null receipt URL, and the zero-cent price case. --- apps/web/src/lib/purchase-emails.test.ts | 329 ++++++++++++++++------- 1 file changed, 232 insertions(+), 97 deletions(-) diff --git a/apps/web/src/lib/purchase-emails.test.ts b/apps/web/src/lib/purchase-emails.test.ts index 1306dc44cf..584f595d7e 100644 --- a/apps/web/src/lib/purchase-emails.test.ts +++ b/apps/web/src/lib/purchase-emails.test.ts @@ -15,11 +15,12 @@ import { SUBSCRIPTION_STARTED_RECOVERY_WINDOW_MS, } from '@/lib/kiloclaw/credit-billing'; import type * as creditBillingModule from '@/lib/kiloclaw/credit-billing'; -import type * as emailModule from '@/lib/email'; import { renderTemplate, buildCreditsTopUpReceiptSection, subjects, + sendCreditsTopUpEmail, + sendKiloClawSubscriptionStartedEmail, type TemplateName, } from '@/lib/email'; @@ -28,62 +29,23 @@ jest.mock('@/lib/firstTopupBonus', () => ({ processFirstTopupBonus: jest.fn(), })); -// Count email sends via the shared `send` export as well as the -// `sendKiloClawSubscriptionStartedEmail` / `sendCreditsTopUpEmail` helpers. -// The helpers are replaced with jest.fns that forward the call via -// sendMock using a synthetic `templateName` so existing tests that filter -// by templateName continue to work. -const sendMock = jest.fn, [unknown]>(async () => ({ - sent: true, +// Mock the outbound transport (Mailgun) and the upstream address-validity +// check (NeverBounce) rather than the helper exports. This way the real +// `send()`, `sendCreditsTopUpEmail`, and `sendKiloClawSubscriptionStartedEmail` +// wiring — formatUsd rounding, formatDate formatting, subjectOverride, +// credits_url / manage_url construction, receipt_section rendering — is +// exercised on every test, so a regression in any of that wiring fails here. +type SendViaMailgunParams = { to: string; subject: string; html: string; replyTo?: string }; +const sendViaMailgunMock = jest.fn, [SendViaMailgunParams]>(async () => true); +const verifyEmailMock = jest.fn, [string]>(async () => true); + +jest.mock('@/lib/email-mailgun', () => ({ + sendViaMailgun: (params: SendViaMailgunParams) => sendViaMailgunMock(params), })); -jest.mock('@/lib/email', () => { - const actual = jest.requireActual('@/lib/email'); - return { - ...actual, - send: jest.fn((params: unknown) => sendMock(params)), - sendCreditsTopUpEmail: jest.fn( - async (props: { - to: string; - variant: 'auto' | 'manual'; - amountCents: number; - creditsCents: number; - purchaseDate: Date; - receiptUrl: string | null; - }) => - sendMock({ - to: props.to, - templateName: 'creditsTopUp', - templateVars: { - amount_usd: (props.amountCents / 100).toFixed(2), - credits_usd: (props.creditsCents / 100).toFixed(2), - receipt_url: props.receiptUrl, - variant: props.variant, - }, - subjectOverride: props.variant === 'auto' ? 'Kilo auto top-up successful' : undefined, - }) - ), - sendKiloClawSubscriptionStartedEmail: jest.fn( - async (props: { - to: string; - planName: string; - priceCents: number; - billingPeriod: string; - nextBillingDate: Date; - }) => - sendMock({ - to: props.to, - templateName: 'kiloClawSubscriptionStarted', - templateVars: { - plan_name: props.planName, - price_usd: (props.priceCents / 100).toFixed(2), - billing_period: props.billingPeriod, - next_billing_date: props.nextBillingDate.toISOString(), - }, - }) - ), - }; -}); +jest.mock('@/lib/email-neverbounce', () => ({ + verifyEmail: (email: string) => verifyEmailMock(email), +})); // Receipt URL lookups during unit tests must not touch Stripe. jest.mock('@/lib/stripe-client', () => ({ @@ -172,13 +134,35 @@ describe('subjects map', () => { }); }); +// Each template has a unique subject line (or a documented subjectOverride), +// so we discriminate Mailgun calls by subject rather than by templateName. +const CREDITS_TOPUP_MANUAL_SUBJECT = subjects.creditsTopUp; +const CREDITS_TOPUP_AUTO_SUBJECT = 'Kilo auto top-up successful'; +const KILOCLAW_SUBSCRIPTION_STARTED_SUBJECT = subjects.kiloClawSubscriptionStarted; + +function creditsTopUpSends(): SendViaMailgunParams[] { + return sendViaMailgunMock.mock.calls + .map(([params]) => params) + .filter( + p => p.subject === CREDITS_TOPUP_MANUAL_SUBJECT || p.subject === CREDITS_TOPUP_AUTO_SUBJECT + ); +} + +function subscriptionStartedSends(): SendViaMailgunParams[] { + return sendViaMailgunMock.mock.calls + .map(([params]) => params) + .filter(p => p.subject === KILOCLAW_SUBSCRIPTION_STARTED_SUBJECT); +} + describe('processTopUp credit top-up email', () => { beforeEach(() => { - sendMock.mockClear(); + sendViaMailgunMock.mockClear(); + verifyEmailMock.mockClear(); }); afterEach(() => { - sendMock.mockClear(); + sendViaMailgunMock.mockClear(); + verifyEmailMock.mockClear(); }); test('sends credit top-up email once for a successful manual top-up', async () => { @@ -194,13 +178,14 @@ describe('processTopUp credit top-up email', () => { }); expect(first).toBe(true); - const topUpSends = sendMock.mock.calls - .map(([params]) => params as { templateName: string; templateVars: Record }) - .filter(p => p.templateName === 'creditsTopUp'); + const topUpSends = creditsTopUpSends(); expect(topUpSends).toHaveLength(1); - expect(topUpSends[0].templateVars.amount_usd).toBe('15.00'); + // $15.00 comes from formatUsd(1500) in the real helper — if formatUsd + // rounding regresses, this assertion fails. + expect(topUpSends[0].html).toContain('$15.00 USD'); + expect(topUpSends[0].to).toBe(user.google_user_email); - sendMock.mockClear(); + sendViaMailgunMock.mockClear(); // Retry / webhook replay with the same stripe_payment_id must not re-send. const second = await processTopUp(user, 1500, { @@ -209,10 +194,7 @@ describe('processTopUp credit top-up email', () => { }); expect(second).toBe(false); - const replayTopUpSends = sendMock.mock.calls - .map(([params]) => params as { templateName: string }) - .filter(p => p.templateName === 'creditsTopUp'); - expect(replayTopUpSends).toHaveLength(0); + expect(creditsTopUpSends()).toHaveLength(0); }); test('uses auto-top-up copy when isAutoTopUp is true', async () => { @@ -228,10 +210,13 @@ describe('processTopUp credit top-up email', () => { { isAutoTopUp: true } ); - const call = sendMock.mock.calls - .map(([params]) => params as { templateName: string; subjectOverride?: string }) - .find(p => p.templateName === 'creditsTopUp'); - expect(call?.subjectOverride).toBe('Kilo auto top-up successful'); + const autoSend = sendViaMailgunMock.mock.calls + .map(([params]) => params) + .find(p => p.subject === CREDITS_TOPUP_AUTO_SUBJECT); + expect(autoSend).toBeTruthy(); + // The auto variant also swaps the heading/intro copy — prove both the + // subject override and the templateVars wiring land. + expect(autoSend?.html).toContain('Your auto top-up was successful'); }); test('does not send an email when skipPostTopUpFreeStuff is true', async () => { @@ -247,10 +232,7 @@ describe('processTopUp credit top-up email', () => { { skipPostTopUpFreeStuff: true } ); - const topUpSends = sendMock.mock.calls - .map(([params]) => params as { templateName: string }) - .filter(p => p.templateName === 'creditsTopUp'); - expect(topUpSends).toHaveLength(0); + expect(creditsTopUpSends()).toHaveLength(0); // Sanity: the credit transaction was still recorded. const [txn] = await db @@ -372,10 +354,12 @@ describe('KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE constant', () => { describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { beforeEach(() => { - sendMock.mockClear(); + sendViaMailgunMock.mockClear(); + verifyEmailMock.mockClear(); }); afterEach(() => { - sendMock.mockClear(); + sendViaMailgunMock.mockClear(); + verifyEmailMock.mockClear(); }); async function applyStripeFundedKiloClawPeriod( @@ -422,10 +406,7 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { } function countSubscriptionStartedSends(): number { - return sendMock.mock.calls.filter( - ([params]) => - (params as { templateName: string }).templateName === 'kiloClawSubscriptionStarted' - ).length; + return subscriptionStartedSends().length; } async function countEmailLogRows(userId: string, instanceId: string): Promise { @@ -550,10 +531,10 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { expect(countSubscriptionStartedSends()).toBe(1); expect(await countEmailLogRows(user.id, instance.id)).toBe(1); - const zeroAmountSend = sendMock.mock.calls - .map(([params]) => params as { templateName: string; templateVars: Record }) - .find(p => p.templateName === 'kiloClawSubscriptionStarted'); - expect(zeroAmountSend?.templateVars.price_usd).toBe('0.00'); + const zeroAmountSend = subscriptionStartedSends()[0]; + expect(zeroAmountSend).toBeTruthy(); + // formatUsd(0) must render "0.00", not "0" or "NaN" — real helper wiring. + expect(zeroAmountSend.html).toContain('$0.00 USD'); }); test('activate → cancel → resubscribe on same instance sends a second subscription-started email', async () => { @@ -587,7 +568,8 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { expect(countSubscriptionStartedSends()).toBe(1); expect(await countEmailLogRows(user.id, instance.id)).toBe(1); - sendMock.mockClear(); + sendViaMailgunMock.mockClear(); + verifyEmailMock.mockClear(); // Simulate cancellation: status=canceled on the same row. await db @@ -778,7 +760,8 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { }); expect(countSubscriptionStartedSends()).toBe(1); - sendMock.mockClear(); + sendViaMailgunMock.mockClear(); + verifyEmailMock.mockClear(); // Same stripe_payment_id → processTopUp returns false (duplicate credit), // so we take the duplicate-recovery path. The kiloclaw_email_log row from @@ -835,7 +818,8 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { eq(kiloclaw_email_log.email_type, KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE) ) ); - sendMock.mockClear(); + sendViaMailgunMock.mockClear(); + verifyEmailMock.mockClear(); await applyStripeFundedKiloClawPeriod({ userId: user.id, @@ -867,10 +851,9 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { stripeSubscriptionId, }); - sendMock.mockImplementationOnce(async () => ({ - sent: false, - reason: 'provider_not_configured' as const, - })); + // Mailgun returns false when MAILGUN_API_KEY/MAILGUN_DOMAIN are missing, + // which `send()` translates into { sent: false, reason: 'provider_not_configured' }. + sendViaMailgunMock.mockImplementationOnce(async () => false); const periodStart = new Date().toISOString(); const periodEnd = new Date(Date.now() + 30 * 86_400_000).toISOString(); @@ -908,10 +891,9 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { stripeSubscriptionId, }); - sendMock.mockImplementationOnce(async () => ({ - sent: false, - reason: 'neverbounce_rejected' as const, - })); + // NeverBounce returns false for invalid/disposable addresses, which + // `send()` translates into { sent: false, reason: 'neverbounce_rejected' }. + verifyEmailMock.mockImplementationOnce(async () => false); const periodStart = new Date().toISOString(); const periodEnd = new Date(Date.now() + 30 * 86_400_000).toISOString(); @@ -928,7 +910,11 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { }); expect(applied).toBe(true); - expect(countSubscriptionStartedSends()).toBe(1); + // verifyEmail was called once for this user (the send attempt), + // so we did try. sendViaMailgun was not reached because verification + // rejected the address — which is the whole point of this branch. + expect(verifyEmailMock).toHaveBeenCalledWith(user.google_user_email); + expect(countSubscriptionStartedSends()).toBe(0); expect(await countEmailLogRows(user.id, instance.id)).toBe(1); }); @@ -982,7 +968,8 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { eq(kiloclaw_email_log.email_type, KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE) ) ); - sendMock.mockClear(); + sendViaMailgunMock.mockClear(); + verifyEmailMock.mockClear(); await applyStripeFundedKiloClawPeriod({ userId: user.id, @@ -999,3 +986,151 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => { expect(await countEmailLogRows(user.id, instance.id)).toBe(0); }); }); + +// ── Direct helper payload tests ──────────────────────────────────────────── +// The surrounding describe blocks mock @/lib/email-mailgun and exercise the +// real helpers through production call sites. These tests assert the exact +// Mailgun payload the helpers emit, protecting: +// - formatUsd rounding +// - formatDate formatting +// - purchase_date / credits_url / receipt_section / manage_url mapping +// - subjectOverride selection + +describe('sendCreditsTopUpEmail payload', () => { + beforeEach(() => { + sendViaMailgunMock.mockClear(); + verifyEmailMock.mockClear(); + }); + + test('manual variant emits the canonical subject, formatted amounts, and a receipt link', async () => { + const result = await sendCreditsTopUpEmail({ + to: 'recipient@example.com', + variant: 'manual', + amountCents: 1500, + creditsCents: 1500, + purchaseDate: new Date('2026-01-15T12:00:00Z'), + receiptUrl: 'https://pay.stripe.com/receipts/abc', + }); + + expect(result).toEqual({ sent: true }); + expect(sendViaMailgunMock).toHaveBeenCalledTimes(1); + const [params] = sendViaMailgunMock.mock.calls[0]; + expect(params.to).toBe('recipient@example.com'); + expect(params.subject).toBe(subjects.creditsTopUp); + // formatUsd(1500) rounding. + expect(params.html).toContain('$15.00 USD'); + // formatDate en-US UTC formatting. + expect(params.html).toContain('January 15, 2026'); + // credits_url construction (NEXTAUTH_URL + '/credits' — http://localhost:3000 in tests). + expect(params.html).toContain('/credits'); + // receipt_section rendering (RawHtml, escaped href). + expect(params.html).toContain('https://pay.stripe.com/receipts/abc'); + expect(params.html).toContain('View your Stripe receipt'); + }); + + test('auto variant overrides the subject and swaps the heading copy', async () => { + await sendCreditsTopUpEmail({ + to: 'recipient@example.com', + variant: 'auto', + amountCents: 2000, + creditsCents: 2000, + purchaseDate: new Date('2026-02-01T00:00:00Z'), + receiptUrl: null, + }); + + const [params] = sendViaMailgunMock.mock.calls[0]; + expect(params.subject).toBe('Kilo auto top-up successful'); + expect(params.html).toContain('Your auto top-up was successful'); + // No receipt URL → receipt section empty, "View your Stripe receipt" absent. + expect(params.html).not.toContain('View your Stripe receipt'); + }); + + test('null receipt URL renders an empty receipt section without breaking the template', async () => { + await sendCreditsTopUpEmail({ + to: 'recipient@example.com', + variant: 'manual', + amountCents: 500, + creditsCents: 500, + purchaseDate: new Date('2026-03-01T00:00:00Z'), + receiptUrl: null, + }); + + const [params] = sendViaMailgunMock.mock.calls[0]; + expect(params.html).toContain('$5.00 USD'); + expect(params.html).not.toContain('View your Stripe receipt'); + }); + + test('neverbounce rejection short-circuits before Mailgun is called', async () => { + verifyEmailMock.mockImplementationOnce(async () => false); + + const result = await sendCreditsTopUpEmail({ + to: 'bad@example.com', + variant: 'manual', + amountCents: 1000, + creditsCents: 1000, + purchaseDate: new Date(), + receiptUrl: null, + }); + + expect(result).toEqual({ sent: false, reason: 'neverbounce_rejected' }); + expect(sendViaMailgunMock).not.toHaveBeenCalled(); + }); + + test('mailgun misconfiguration surfaces as provider_not_configured', async () => { + sendViaMailgunMock.mockImplementationOnce(async () => false); + + const result = await sendCreditsTopUpEmail({ + to: 'recipient@example.com', + variant: 'manual', + amountCents: 1000, + creditsCents: 1000, + purchaseDate: new Date(), + receiptUrl: null, + }); + + expect(result).toEqual({ sent: false, reason: 'provider_not_configured' }); + }); +}); + +describe('sendKiloClawSubscriptionStartedEmail payload', () => { + beforeEach(() => { + sendViaMailgunMock.mockClear(); + verifyEmailMock.mockClear(); + }); + + test('emits the canonical subject, formatted price/next-billing-date, and the manage link', async () => { + const result = await sendKiloClawSubscriptionStartedEmail({ + to: 'recipient@example.com', + planName: 'KiloClaw Standard', + priceCents: 900, + billingPeriod: 'Jan 15, 2026 – Feb 15, 2026', + nextBillingDate: new Date('2026-02-15T00:00:00Z'), + }); + + expect(result).toEqual({ sent: true }); + const [params] = sendViaMailgunMock.mock.calls[0]; + expect(params.to).toBe('recipient@example.com'); + expect(params.subject).toBe(subjects.kiloClawSubscriptionStarted); + expect(params.html).toContain('KiloClaw Standard'); + // formatUsd(900). + expect(params.html).toContain('$9.00 USD'); + expect(params.html).toContain('Jan 15, 2026 – Feb 15, 2026'); + // formatDate(next billing). + expect(params.html).toContain('February 15, 2026'); + // manage_url construction (NEXTAUTH_URL + '/claw'). + expect(params.html).toContain('/claw'); + }); + + test('zero-cent price still renders "$0.00 USD" (formatUsd rounding)', async () => { + await sendKiloClawSubscriptionStartedEmail({ + to: 'recipient@example.com', + planName: 'KiloClaw Standard', + priceCents: 0, + billingPeriod: 'Jan 1, 2026 – Feb 1, 2026', + nextBillingDate: new Date('2026-02-01T00:00:00Z'), + }); + + const [params] = sendViaMailgunMock.mock.calls[0]; + expect(params.html).toContain('$0.00 USD'); + }); +});