diff --git a/bin/brakit.ts b/bin/brakit.ts
index c2a094e..093edae 100644
--- a/bin/brakit.ts
+++ b/bin/brakit.ts
@@ -4,7 +4,7 @@ import { resolve } from "node:path";
 import installCommand from "../src/cli/commands/install.js";
 import uninstallCommand from "../src/cli/commands/uninstall.js";
 import { trackEvent } from "../src/telemetry/index.js";
-import { TELEMETRY_EVENT_CLI_INVOKED } from "../src/constants/config.js";
+import { TELEMETRY_EVENT_CLI_INVOKED } from "../src/constants/telemetry.js";
 
 const sub = process.argv[2];
 const command = sub === "uninstall" ? "uninstall" : sub === "mcp" ? "mcp" : "install";
diff --git a/sdks/python/brakit/_setup.py b/sdks/python/brakit/_setup.py
index 6bca625..85904f1 100644
--- a/sdks/python/brakit/_setup.py
+++ b/sdks/python/brakit/_setup.py
@@ -5,6 +5,7 @@
 import logging
 import threading
 import time
+from typing import TYPE_CHECKING
 
 from brakit.constants.events import (
     CHANNEL_REQUEST_COMPLETED,
@@ -25,10 +26,15 @@
 from brakit.types.http import TracedRequest
 from brakit.types.telemetry import TelemetryEntry
 
+if TYPE_CHECKING:
+    from brakit.core.registry import ServiceRegistry
+    from brakit.transport.forwarder import Forwarder
+
 logger = logging.getLogger(LOGGER_NAME)
 
 _init_lock = threading.Lock()
 _initialized = False
+_detected_stack: dict[str, object] = {"framework": "unknown", "adapters": []}
 
 
 def _auto_setup() -> None:
@@ -47,13 +53,17 @@ def _auto_setup() -> None:
     adapters = _install_adapters(registry)
     logger.debug("adapters: %s", adapters)
 
-    _start_transport(registry)
     detected_framework = _install_frameworks(registry)
 
-    # Initialize telemetry after framework detection
+    _detected_stack["framework"] = detected_framework
+    _detected_stack["adapters"] = adapters
+
     from brakit._telemetry import init_session as _init_telemetry
     _init_telemetry(framework=detected_framework, adapters=adapters)
 
+    # Start transport after stack is known so sdk.hello includes full info
+    _start_transport(registry)
+
     logger.debug("initialized")
 
 
@@ -99,9 +109,6 @@ def _start_transport(registry: "ServiceRegistry") -> None:
         _setup_forwarder(registry, port)
         return
 
-    # Port file not found — the Node.js server may not have received its first
-    # request yet (the port file is written on first request, not on startup).
-    # Retry discovery in a background thread so we don't block import.
     def _retry() -> None:
         for _ in range(PORT_RETRY_COUNT):
             time.sleep(PORT_RETRY_INTERVAL_S)
@@ -125,6 +132,8 @@ def _setup_forwarder(registry: "ServiceRegistry", port: int) -> None:
     forwarder = Forwarder(port=port)
     forwarder.start()
 
+    _send_hello(forwarder)
+
     registry.bus.on(CHANNEL_REQUEST_COMPLETED, lambda r: _forward_request(forwarder, r))
     registry.bus.on(CHANNEL_TELEMETRY_FETCH, lambda e: _forward_telemetry(forwarder, EVENT_TYPE_FETCH, e))
     registry.bus.on(CHANNEL_TELEMETRY_LOG, lambda e: _forward_telemetry(forwarder, EVENT_TYPE_LOG, e))
@@ -140,6 +149,24 @@ def _install_frameworks(registry: "ServiceRegistry") -> str:
     return detect_frameworks(registry)
 
 
+def _send_hello(forwarder: "Forwarder") -> None:
+    import platform
+    import sys
+
+    event = SDKEvent(
+        type="sdk.hello",  # type: ignore[arg-type]
+        timestamp=time.time() * 1_000,
+        data={
+            "framework": str(_detected_stack["framework"]),
+            "adapters": list(_detected_stack["adapters"]),  # type: ignore[arg-type]
+            "pythonVersion": platform.python_version(),
+            "os": f"{sys.platform}-{platform.release()}",
+            "arch": platform.machine(),
+        },
+    )
+    forwarder.send(event)
+
+
 def _forward_request(forwarder: "Forwarder", request: TracedRequest) -> None:
     raw = dataclasses.asdict(request)
     data = {_to_camel(k): v for k, v in raw.items()}
diff --git a/sdks/python/pyproject.toml b/sdks/python/pyproject.toml
index b8d8dfb..07574ae 100644
--- a/sdks/python/pyproject.toml
+++ b/sdks/python/pyproject.toml
@@ -4,7 +4,7 @@ build-backend = "hatchling.build"
 
 [project]
 name = "brakit"
-version = "0.1.6"
+version = "0.1.7"
 description = "Zero-config observability for Python web frameworks"
 readme = "README.md"
 license = "MIT"
diff --git a/src/cli/commands/uninstall.ts b/src/cli/commands/uninstall.ts
index 23f534d..b7bb437 100644
--- a/src/cli/commands/uninstall.ts
+++ b/src/cli/commands/uninstall.ts
@@ -24,7 +24,7 @@ import {
 import { brakitDebug } from "../../utils/log.js";
 import { getErrorMessage } from "../../utils/type-guards.js";
 import { trackEvent } from "../../telemetry/index.js";
-import { TELEMETRY_EVENT_CLI_UNINSTALL } from "../../constants/config.js";
+import { TELEMETRY_EVENT_CLI_UNINSTALL } from "../../constants/telemetry.js";
 
 /**
  * Entry point files where brakit may have prepended an import line.
diff --git a/src/constants/config.ts b/src/constants/config.ts
index bcfb583..b444b4e 100644
--- a/src/constants/config.ts
+++ b/src/constants/config.ts
@@ -135,32 +135,6 @@ export const VALID_ISSUE_CATEGORIES = new Set<IssueCategory>(["security", "perfo
 export const VALID_AI_FIX_STATUSES = new Set<AiFixStatus>(["fixed", "wont_fix"]);
 export const VALID_SECURITY_SEVERITIES = new Set<SecuritySeverity>(["critical", "warning"]);
 
-// ── Telemetry ──
-
-export const TELEMETRY_EVENT_CLI_INVOKED = "cli_invoked" as const;
-export const TELEMETRY_EVENT_CLI_UNINSTALL = "cli_uninstall" as const;
-export const TELEMETRY_EVENT_SETUP_COMPLETED = "setup_completed" as const;
-export const TELEMETRY_EVENT_FIRST_REQUEST = "first_request" as const;
-export const TELEMETRY_EVENT_DASHBOARD_VIEWED = "dashboard_viewed" as const;
-export const TELEMETRY_EVENT_SESSION = "session" as const;
-export const TELEMETRY_EVENT_GRAPH_FEATURE = "graph_feature" as const;
-
-export const EXIT_REASON_CLEAN = "clean" as const;
-export const EXIT_REASON_SIGINT = "sigint" as const;
-export const EXIT_REASON_SIGTERM = "sigterm" as const;
-export const EXIT_REASON_UNKNOWN = "unknown" as const;
 
 /** Max characters for SQL/query detail preview in insight cards. */
 export const DETAIL_PREVIEW_LENGTH = 120;
-
-/**
- * Known dependency names to check for framework/ORM detection.
- * Used for telemetry diagnostics — captures which deps exist in
- * the user's package.json (names only, no versions or paths).
- */
-export const KNOWN_DEPENDENCY_NAMES = [
-  "next", "@remix-run/dev", "nuxt", "vite", "astro",
-  "@nestjs/core", "@adonisjs/core", "sails",
-  "express", "fastify", "hono", "koa", "@hapi/hapi",
-  "prisma", "drizzle-orm", "typeorm", "sequelize",
-] as const;
diff --git a/src/constants/detection.ts b/src/constants/detection.ts
new file mode 100644
index 0000000..4ef9f6a
--- /dev/null
+++ b/src/constants/detection.ts
@@ -0,0 +1,74 @@
+import type { HookName } from "../types/detection.js";
+
+/** Segment used to identify node_modules paths in require.cache keys. */
+export const NODE_MODULES_SEGMENT = "/node_modules/";
+
+/** Hooks installed during Brakit setup. */
+export const INSTALLED_HOOKS: readonly HookName[] = ["fetch", "console", "error"];
+
+/**
+ * Known public package names for stack detection.
+ * Matched against package.json dependencies and require.cache at runtime.
+ * Only public npm package names — no versions, paths, or private scopes.
+ */
+export const KNOWN_DEPENDENCY_NAMES = [
+  // -- Frameworks (meta) --
+  "next", "@remix-run/dev", "nuxt", "astro",
+  // -- Frameworks (backend) --
+  "@nestjs/core", "@adonisjs/core", "sails",
+  "express", "fastify", "hono", "koa", "@hapi/hapi",
+  "elysia", "h3", "nitro", "@trpc/server",
+  // -- Bundlers --
+  "vite",
+  // -- ORM / query builders --
+  "prisma", "@prisma/client", "drizzle-orm", "typeorm", "sequelize",
+  "mongoose", "kysely", "knex", "@mikro-orm/core", "objection",
+  // -- DB drivers --
+  "pg", "mysql2", "mongodb", "better-sqlite3",
+  "@libsql/client", "@planetscale/database",
+  "ioredis", "redis",
+  // -- Auth --
+  "lucia", "next-auth", "@auth/core", "passport",
+  // -- Queues / messaging --
+  "bullmq", "amqplib", "kafkajs",
+  // -- Validation --
+  "zod", "joi", "yup", "arktype", "valibot",
+  // -- HTTP clients --
+  "axios", "got", "ky", "undici",
+  // -- Realtime --
+  "socket.io", "ws",
+  // -- CSS / styling --
+  "tailwindcss",
+  // -- Testing --
+  "vitest", "jest", "mocha",
+  // -- Runtime indicators --
+  "bun-types", "@types/bun",
+] as const;
+
+/**
+ * Config file paths → tool labels for stack detection.
+ * Detection checks file existence only (existsSync), never reads contents.
+ */
+export const KNOWN_CONFIG_FILES = {
+  "next.config.js": "nextjs",
+  "next.config.mjs": "nextjs",
+  "next.config.ts": "nextjs",
+  "nuxt.config.ts": "nuxt",
+  "nuxt.config.js": "nuxt",
+  "astro.config.mjs": "astro",
+  "astro.config.ts": "astro",
+  "vite.config.ts": "vite",
+  "vite.config.js": "vite",
+  "drizzle.config.ts": "drizzle-orm",
+  "drizzle.config.js": "drizzle-orm",
+  "prisma/schema.prisma": "prisma",
+  "knexfile.js": "knex",
+  "knexfile.ts": "knex",
+  "mikro-orm.config.ts": "@mikro-orm/core",
+  "nest-cli.json": "@nestjs/core",
+  "tailwind.config.js": "tailwindcss",
+  "tailwind.config.ts": "tailwindcss",
+} as const;
+
+/** Pre-built Set for O(1) lookups during require.cache scanning. */
+export const KNOWN_DEPENDENCY_SET: ReadonlySet<string> = new Set(KNOWN_DEPENDENCY_NAMES);
diff --git a/src/constants/index.ts b/src/constants/index.ts
index 8bb6d90..7a7f05c 100644
--- a/src/constants/index.ts
+++ b/src/constants/index.ts
@@ -1,3 +1,5 @@
 export * from "./config.js";
+export * from "./detection.js";
 export * from "./labels.js";
 export * from "./features.js";
+export * from "./telemetry.js";
diff --git a/src/constants/labels.ts b/src/constants/labels.ts
index 1aa186c..4f80231 100644
--- a/src/constants/labels.ts
+++ b/src/constants/labels.ts
@@ -100,21 +100,8 @@ export const SDK_EVENT_FETCH = "fetch" as const;
 export const SDK_EVENT_LOG = "log" as const;
 export const SDK_EVENT_ERROR = "error" as const;
 export const SDK_EVENT_AUTH_CHECK = "auth.check" as const;
+export const SDK_EVENT_HELLO = "sdk.hello" as const;
 
-// ── Telemetry ──
-
-export const POSTHOG_HOST = "https://us.i.posthog.com";
-export const POSTHOG_CAPTURE_PATH = "/i/v0/e/";
-export const POSTHOG_REQUEST_TIMEOUT_MS = 3_000;
-export const POSTHOG_SPAWN_TIMEOUT_MS = 5_000;
-export const SIGNAL_EXIT_SIGINT = 130;
-export const SIGNAL_EXIT_SIGTERM = 143;
-
-/**
- * Thresholds (in ms) for categorizing endpoint response times
- * into human-readable buckets for telemetry reporting.
- */
-export const SPEED_BUCKET_THRESHOLDS = [200, 500, 1_000, 2_000, 5_000] as const;
 
 // ── Timeline ──
 
@@ -124,3 +111,9 @@ export const TIMELINE_FETCH = "fetch" as const;
 export const TIMELINE_LOG = "log" as const;
 export const TIMELINE_ERROR = "error" as const;
 export const TIMELINE_QUERY = "query" as const;
+
+// ── Unicode symbols ──
+
+export const UNICODE_ARROW = "\u2192";
+export const UNICODE_EM_DASH = "\u2014";
+export const UNICODE_CHECK_MARK = "\u2713";
diff --git a/src/constants/telemetry.ts b/src/constants/telemetry.ts
new file mode 100644
index 0000000..781178c
--- /dev/null
+++ b/src/constants/telemetry.ts
@@ -0,0 +1,37 @@
+// ── PostHog transport ──
+
+export const POSTHOG_HOST = "https://us.i.posthog.com";
+export const POSTHOG_CAPTURE_PATH = "/i/v0/e/";
+export const POSTHOG_REQUEST_TIMEOUT_MS = 3_000;
+
+// ── Telemetry event names ──
+
+export const TELEMETRY_EVENT_CLI_INVOKED = "cli_invoked" as const;
+export const TELEMETRY_EVENT_CLI_UNINSTALL = "cli_uninstall" as const;
+export const TELEMETRY_EVENT_SETUP_COMPLETED = "setup_completed" as const;
+export const TELEMETRY_EVENT_FIRST_REQUEST = "first_request" as const;
+export const TELEMETRY_EVENT_DASHBOARD_VIEWED = "dashboard_viewed" as const;
+export const TELEMETRY_EVENT_SESSION = "session" as const;
+export const TELEMETRY_EVENT_GRAPH_FEATURE = "graph_feature" as const;
+
+export const TELEMETRY_SDK_NAME = "node" as const;
+
+// ── Exit reasons ──
+
+export const EXIT_REASON_CLEAN = "clean" as const;
+export const EXIT_REASON_SIGINT = "sigint" as const;
+export const EXIT_REASON_SIGTERM = "sigterm" as const;
+export const EXIT_REASON_UNKNOWN = "unknown" as const;
+
+// ── Signal codes ──
+
+export const SIGNAL_EXIT_SIGINT = 130;
+export const SIGNAL_EXIT_SIGTERM = 143;
+
+// ── Speed buckets ──
+
+/**
+ * Thresholds (in ms) for categorizing endpoint response times
+ * into human-readable buckets for telemetry reporting.
+ */
+export const SPEED_BUCKET_THRESHOLDS = [200, 500, 1_000, 2_000, 5_000] as const;
diff --git a/src/dashboard/api/ingest.ts b/src/dashboard/api/ingest.ts
index 01b25ef..3fe97f3 100644
--- a/src/dashboard/api/ingest.ts
+++ b/src/dashboard/api/ingest.ts
@@ -6,6 +6,8 @@ import { MAX_INGEST_BYTES } from "../../constants/config.js";
 import { HTTP_NO_CONTENT, HTTP_BAD_REQUEST, HTTP_METHOD_NOT_ALLOWED, HTTP_PAYLOAD_TOO_LARGE, TIMELINE_FETCH, TIMELINE_LOG, TIMELINE_ERROR, TIMELINE_QUERY } from "../../constants/labels.js";
 import { sendJson } from "./shared.js";
 import { routeSDKEvent } from "./sdk-event-parser.js";
+import { SDK_EVENT_HELLO } from "../../constants/labels.js";
+import { session } from "../../telemetry/index.js";
 
 function isBrakitBatch(msg: unknown): msg is TelemetryBatch {
   return (
@@ -81,6 +83,15 @@ export function createIngestHandler(
 
         if (isSDKPayload(body)) {
           for (const event of body.events) {
+            if (event.type === SDK_EVENT_HELLO) {
+              const d = event.data as Record<string, unknown>;
+              session.recordPythonStack({
+                framework: String(d.framework ?? "unknown"),
+                adapters: Array.isArray(d.adapters) ? d.adapters.map(String) : [],
+                pythonVersion: String(d.pythonVersion ?? "unknown"),
+              });
+              continue;
+            }
             routeSDKEvent(event, stores);
           }
           res.writeHead(HTTP_NO_CONTENT);
diff --git a/src/dashboard/client/views/insights-view.ts b/src/dashboard/client/views/insights-view.ts
index 86efe7a..74d4f25 100644
--- a/src/dashboard/client/views/insights-view.ts
+++ b/src/dashboard/client/views/insights-view.ts
@@ -78,7 +78,12 @@ export class InsightsView extends BkViewBase {
         `)}
       </div>
 
+      ${this.renderSummaryBar(nonStale)}
+
       <div class="insights-list">
+        ${(open.length + regressed.length) > 0 ? html`
+          <div class="insights-ai-hint">Copy to your AI: <code>"Fix brakit findings"</code></div>
+        ` : nothing}
         ${open.length === 0 && regressed.length === 0 && verifying.length === 0 && resolved.length === 0 && dismissed.length === 0
           ? html`<div class="insights-empty"><span class="insights-empty-icon">\u2713</span>${this.filter === "all" ? "All clear \u2014 no issues detected" : `No ${this.filter} issues`}</div>`
           : nothing}
@@ -126,6 +131,23 @@ export class InsightsView extends BkViewBase {
     `;
   }
 
+  private renderSummaryBar(nonStale: StatefulIssue[]) {
+    const active = nonStale.filter((e) => (e.state === "open" || e.state === "regressed") && e.aiStatus !== "wont_fix");
+    const critical = active.filter((e) => e.issue.severity === "critical").length;
+    const warning = active.filter((e) => e.issue.severity === "warning").length;
+    const resolved = nonStale.filter((e) => e.state === "resolved").length;
+
+    if (critical === 0 && warning === 0 && resolved === 0) return nothing;
+
+    return html`
+      <div class="insights-summary">
+        ${critical > 0 ? html`<span class="insights-summary-stat critical">${critical} critical</span>` : nothing}
+        ${warning > 0 ? html`<span class="insights-summary-stat warning">${warning} warning</span>` : nothing}
+        ${resolved > 0 ? html`<span class="insights-summary-stat resolved">${resolved} resolved</span>` : nothing}
+      </div>
+    `;
+  }
+
   private renderIssueCard(entry: StatefulIssue, idx: number) {
     const issue = entry.issue;
     const severityConfig = SEVERITY_MAP[issue.severity] || SEVERITY_MAP["info"];
@@ -150,11 +172,13 @@ export class InsightsView extends BkViewBase {
             ${isResolved ? html`<span class="insights-badge-resolved">resolved</span>` : nothing}
           </div>
           <div class="insights-card-desc">${issue.desc}</div>
-          ${issue.detail ? html`<div class="insights-card-detail">${issue.detail}</div>` : nothing}
-          ${entry.cleanHitsSinceLastSeen > 0 ? html`
-            <div class="insights-card-progress">${entry.cleanHitsSinceLastSeen}/${CLEAN_HITS_FOR_RESOLUTION} clean requests</div>
+          ${isExpanded ? html`
+            ${issue.detail ? html`<div class="insights-card-detail">${issue.detail}</div>` : nothing}
+            ${entry.cleanHitsSinceLastSeen > 0 ? html`
+              <div class="insights-card-progress">${entry.cleanHitsSinceLastSeen}/${CLEAN_HITS_FOR_RESOLUTION} clean requests</div>
+            ` : nothing}
+            ${issue.hint ? html`<div class="insights-card-hint">${issue.hint}</div>` : nothing}
           ` : nothing}
-          ${isExpanded && issue.hint ? html`<div class="insights-card-hint">${issue.hint}</div>` : nothing}
         </div>
         ${issue.hint ? html`<span class="insights-card-arrow">${isExpanded ? "\u2193" : "\u2192"}</span>` : nothing}
       </div>
diff --git a/src/dashboard/router.ts b/src/dashboard/router.ts
index 068b2d8..55a8440 100644
--- a/src/dashboard/router.ts
+++ b/src/dashboard/router.ts
@@ -53,8 +53,7 @@ import { createGraphHandler } from "./api/graph.js";
 import { createSSEHandler } from "./sse.js";
 import { getDashboardHtml } from "./page.js";
 import {
-  recordTabViewed,
-  recordDashboardOpened,
+  session,
   recordGraphFeature,
   isTelemetryEnabled,
 } from "../telemetry/index.js";
@@ -101,7 +100,7 @@ export function createDashboardHandler(
       const url = new URL(req.url ?? "/", "http://localhost");
       const tab = url.searchParams.get("tab");
       if (tab && tab.length <= MAX_TAB_NAME_LENGTH && VALID_TABS.has(tab as DashboardView)) {
-        recordTabViewed(tab);
+        session.recordTabViewed(tab);
       }
       const event = url.searchParams.get("event");
       if (event && event.length <= MAX_TAB_NAME_LENGTH) {
@@ -122,7 +121,7 @@ export function createDashboardHandler(
       return;
     }
 
-    if (isTelemetryEnabled()) recordDashboardOpened();
+    if (isTelemetryEnabled()) session.recordDashboardOpened();
     res.writeHead(HTTP_OK, {
       "content-type": "text/html; charset=utf-8",
       "cache-control": "no-cache",
diff --git a/src/dashboard/styles/insights.ts b/src/dashboard/styles/insights.ts
index 4824dfc..e7bbba2 100644
--- a/src/dashboard/styles/insights.ts
+++ b/src/dashboard/styles/insights.ts
@@ -8,13 +8,24 @@ export function getInsightsStyles(): string {
 .insights-chip-count{font-size:10px;font-family:var(--mono);background:rgba(0,0,0,.08);padding:1px 5px;border-radius:8px}
 .insights-chip.active .insights-chip-count{background:rgba(255,255,255,.25)}
 
+/* Summary bar */
+.insights-summary{display:flex;gap:14px;padding:10px 28px;font-size:12px;font-weight:500;border-bottom:1px solid var(--border)}
+.insights-summary-stat{display:flex;align-items:center;gap:4px}
+.insights-summary-stat.critical{color:var(--red)}
+.insights-summary-stat.warning{color:var(--amber)}
+.insights-summary-stat.resolved{color:var(--green)}
+
+/* AI hint */
+.insights-ai-hint{font-size:11px;color:var(--text-muted);padding:0 0 12px}
+.insights-ai-hint code{background:var(--bg-muted);padding:2px 6px;border-radius:4px;font-family:var(--mono);font-size:11px}
+
 /* Insights card list */
 .insights-list{padding:16px 28px}
 
 .insights-empty{display:flex;align-items:center;gap:10px;padding:24px;color:var(--green);font-size:14px;font-weight:500}
 .insights-empty-icon{font-size:18px}
 
-.insights-card{display:flex;align-items:flex-start;gap:12px;padding:14px 18px;background:var(--bg-card);border:1px solid var(--border);border-radius:10px;cursor:pointer;transition:all .15s;margin-bottom:8px}
+.insights-card{display:flex;align-items:flex-start;gap:12px;padding:12px 16px;background:var(--bg-card);border:1px solid var(--border);border-radius:10px;cursor:pointer;transition:all .15s;margin-bottom:6px}
 .insights-card:hover{border-color:var(--border-light);box-shadow:0 2px 8px rgba(0,0,0,.04)}
 .insights-card.expanded{border-color:var(--border-light);box-shadow:0 2px 8px rgba(0,0,0,.04)}
 .insights-card.resolved{opacity:.55}
diff --git a/src/detect/project.ts b/src/detect/project.ts
index bf522ee..62d5049 100644
--- a/src/detect/project.ts
+++ b/src/detect/project.ts
@@ -3,6 +3,7 @@ import { existsSync } from "node:fs";
 import { join, relative } from "node:path";
 import type { Framework, DetectedProject, DetectedPythonProject, PythonPackageManager } from "../types/index.js";
 import { fileExists } from "../utils/fs.js";
+import { KNOWN_CONFIG_FILES } from "../constants/detection.js";
 
 export type PackageManager = DetectedProject["packageManager"];
 
@@ -49,22 +50,11 @@ export async function detectProject(
   const devBin = matched ? join(rootDir, "node_modules", ".bin", matched.bin) : "";
   const defaultPort = matched?.defaultPort ?? 3000;
 
-  const packageManager = await detectPackageManager(rootDir);
+  const packageManager = detectPackageManager(rootDir);
 
   return { framework, devCommand, devBin, defaultPort, packageManager };
 }
 
-async function detectPackageManager(
-  rootDir: string,
-): Promise<PackageManager> {
-  if (await fileExists(join(rootDir, "bun.lockb"))) return "bun";
-  if (await fileExists(join(rootDir, "bun.lock"))) return "bun";
-  if (await fileExists(join(rootDir, "pnpm-lock.yaml"))) return "pnpm";
-  if (await fileExists(join(rootDir, "yarn.lock"))) return "yarn";
-  if (await fileExists(join(rootDir, "package-lock.json"))) return "npm";
-  return "unknown";
-}
-
 /** Match framework from a merged dependencies object. */
 export function detectFrameworkFromDeps(allDeps: Record<string, unknown>): Framework {
   for (const f of FRAMEWORKS) {
@@ -73,8 +63,16 @@ export function detectFrameworkFromDeps(allDeps: Record<string, unknown>): Frame
   return "unknown";
 }
 
-/** Synchronous package manager detection via lock-file presence. */
-export function detectPackageManagerSync(rootDir: string): PackageManager {
+export function detectConfigFiles(rootDir: string): string[] {
+  const found = new Set<string>();
+  for (const [file, label] of Object.entries(KNOWN_CONFIG_FILES)) {
+    if (existsSync(join(rootDir, file))) found.add(label);
+  }
+  return [...found];
+}
+
+/** Detect package manager from lock-file presence. */
+export function detectPackageManager(rootDir: string): PackageManager {
   if (existsSync(join(rootDir, "bun.lockb")) || existsSync(join(rootDir, "bun.lock"))) return "bun";
   if (existsSync(join(rootDir, "pnpm-lock.yaml"))) return "pnpm";
   if (existsSync(join(rootDir, "yarn.lock"))) return "yarn";
diff --git a/src/detect/runtime.ts b/src/detect/runtime.ts
new file mode 100644
index 0000000..bb8e9bc
--- /dev/null
+++ b/src/detect/runtime.ts
@@ -0,0 +1,41 @@
+import type { JsRuntime } from "../types/detection.js";
+import { NODE_MODULES_SEGMENT, KNOWN_DEPENDENCY_SET } from "../constants/detection.js";
+
+export function detectJsRuntime(): JsRuntime {
+  if ((globalThis as Record<string, unknown>).Bun) return "bun";
+  if ((globalThis as Record<string, unknown>).Deno) return "deno";
+  return "node";
+}
+
+/**
+ * Scan require.cache for known packages that are actually loaded at runtime.
+ * Returns only names that match KNOWN_DEPENDENCY_SET — no private packages leak.
+ * Handles both Unix (/) and Windows (\) path separators.
+ */
+export function extractLoadedPackages(): string[] {
+  try {
+    const cache = require.cache;
+    if (!cache) return [];
+
+    const seen = new Set<string>();
+    const segment = NODE_MODULES_SEGMENT;
+    const segmentWin = segment.replaceAll("/", "\\");
+
+    for (const key of Object.keys(cache)) {
+      const nm = Math.max(key.lastIndexOf(segment), key.lastIndexOf(segmentWin));
+      if (nm === -1) continue;
+
+      const after = key.slice(nm + segment.length);
+      const parts = after.split(/[/\\]/);
+      const pkgName = parts[0]!.startsWith("@")
+        ? `${parts[0]}/${parts[1]}`
+        : parts[0]!;
+
+      if (KNOWN_DEPENDENCY_SET.has(pkgName)) seen.add(pkgName);
+    }
+
+    return [...seen];
+  } catch {
+    return [];
+  }
+}
diff --git a/src/output/terminal.ts b/src/output/terminal.ts
index 7e84244..2e92f9a 100644
--- a/src/output/terminal.ts
+++ b/src/output/terminal.ts
@@ -1,19 +1,9 @@
 import pc from "picocolors";
 import { VERSION } from "../index.js";
-import { DASHBOARD_PREFIX } from "../constants/index.js";
-import { TERMINAL_TRUNCATE_LENGTH } from "../constants/config.js";
-import { SEVERITY_ICON } from "../constants/labels.js";
-import type { Severity } from "../types/security.js";
-import type { Issue } from "../types/issue-lifecycle.js";
+import { DASHBOARD_PREFIX, UNICODE_ARROW, UNICODE_EM_DASH, UNICODE_CHECK_MARK } from "../constants/index.js";
 import type { Services } from "../core/services.js";
 import type { AnalysisUpdate } from "../core/event-bus.js";
 
-const SEVERITY_COLOR: Record<Severity, (s: string) => string> = {
-  critical: pc.red,
-  warning: pc.yellow,
-  info: pc.dim,
-};
-
 function print(line: string): void {
   process.stdout.write(line + "\n");
 }
@@ -34,28 +24,8 @@ export function printBanner(proxyPort: number, targetPort: number): void {
   print("");
 }
 
-function severityIcon(severity: Severity): string {
-  return SEVERITY_COLOR[severity](SEVERITY_ICON[severity]);
-}
-
-function colorTitle(severity: Severity, text: string): string {
-  const color = SEVERITY_COLOR[severity];
-  return severity === "info" ? color(text) : color(pc.bold(text));
-}
-
-function truncate(s: string, max = TERMINAL_TRUNCATE_LENGTH): string {
-  return s.length <= max ? s : s.slice(0, max - 1) + "\u2026";
-}
-
-function formatConsoleLine(issue: Issue, suffix?: string): string {
-  const icon = severityIcon(issue.severity);
-  const title = colorTitle(issue.severity, issue.title);
-  const desc = pc.dim(truncate(issue.desc) + (suffix ?? ""));
-  let line = `  ${icon} ${title} \u2014 ${desc}`;
-  if (issue.detail) {
-    line += `\n    ${pc.dim("\u2514 " + issue.detail)}`;
-  }
-  return line;
+function pluralize(n: number, word: string): string {
+  return n === 1 ? `${n} ${word}` : `${n} ${word}s`;
 }
 
 export function startTerminalInsights(
@@ -63,15 +33,16 @@ export function startTerminalInsights(
   proxyPort: number,
 ): () => void {
   const bus = services.bus;
-  const metricsStore = services.metricsStore;
   const printedKeys = new Set<string>();
   const resolvedKeys = new Set<string>();
-  const dashUrl = `localhost:${proxyPort}${DASHBOARD_PREFIX}`;
+  const dashUrl = `http://localhost:${proxyPort}${DASHBOARD_PREFIX}`;
+  const prefix = `  ${pc.magenta(pc.bold("brakit"))} ${pc.dim(UNICODE_ARROW)}`;
+  const actionHint = `${pc.underline(dashUrl)} ${pc.dim("or run")} ${pc.bold('"Fix brakit findings"')} ${pc.dim("in your AI tool")}`;
 
   return bus.on("analysis:updated", ({ issues }: AnalysisUpdate) => {
-    const newLines: string[] = [];
-    const resolvedLines: string[] = [];
-    const regressedLines: string[] = [];
+    let newCount = 0;
+    let resolvedCount = 0;
+    let regressedCount = 0;
 
     for (const si of issues) {
       if (si.aiStatus === "wont_fix") continue;
@@ -80,9 +51,7 @@ export function startTerminalInsights(
         if (resolvedKeys.has(si.issueId)) continue;
         resolvedKeys.add(si.issueId);
         printedKeys.delete(si.issueId);
-        const title = pc.green(pc.bold(`\u2713 ${si.issue.title}`));
-        const desc = pc.dim(truncate(si.issue.desc));
-        resolvedLines.push(`  ${title} \u2014 ${desc} ${pc.green("resolved")}`);
+        resolvedCount++;
         continue;
       }
 
@@ -90,9 +59,7 @@ export function startTerminalInsights(
         if (!printedKeys.has(si.issueId)) {
           printedKeys.add(si.issueId);
           resolvedKeys.delete(si.issueId);
-          const title = pc.red(pc.bold(`\u26A0 ${si.issue.title}`));
-          const desc = pc.dim(truncate(si.issue.desc));
-          regressedLines.push(`  ${title} \u2014 ${desc} ${pc.red("regressed")}`);
+          regressedCount++;
         }
         continue;
       }
@@ -101,41 +68,22 @@ export function startTerminalInsights(
       if (si.issue.severity === "info") continue;
       if (printedKeys.has(si.issueId)) continue;
       printedKeys.add(si.issueId);
-
-      let suffix: string | undefined;
-      if (si.issue.rule === "slow") {
-        const endpoint = si.issue.endpoint;
-        if (endpoint) {
-          const ep = metricsStore.getEndpoint(endpoint);
-          if (ep && ep.sessions.length > 1) {
-            const prev = ep.sessions[ep.sessions.length - 2];
-            suffix = ` (\u2191 from ${prev.p95DurationMs < 1000 ? prev.p95DurationMs + "ms" : (prev.p95DurationMs / 1000).toFixed(1) + "s"})`;
-          }
-        }
-      }
-
-      newLines.push(formatConsoleLine(si.issue, suffix));
+      newCount++;
     }
 
-    if (newLines.length > 0) {
+    if (newCount > 0) {
       print("");
-      for (const line of newLines) print(line);
-      print("");
-      print(`  ${pc.magenta(pc.bold("brakit"))} ${pc.dim("\u2192")} ${pc.dim("Dashboard:")} ${pc.underline(`http://${dashUrl}`)}  ${pc.dim("or ask your AI:")} ${pc.bold('"Fix brakit findings"')}`);
+      print(`${prefix} ${pc.yellow(pluralize(newCount, "new issue"))} ${pc.dim(UNICODE_EM_DASH)} ${actionHint}`);
     }
 
-    if (regressedLines.length > 0) {
-      print("");
-      for (const line of regressedLines) print(line);
+    if (regressedCount > 0) {
       print("");
-      print(`  ${pc.magenta(pc.bold("brakit"))} ${pc.dim("\u2192")} ${pc.red("Issues came back after being resolved!")}`);
+      print(`${prefix} ${pc.red(pluralize(regressedCount, "issue") + " regressed")} ${pc.dim(UNICODE_EM_DASH)} ${actionHint}`);
     }
 
-    if (resolvedLines.length > 0) {
-      print("");
-      for (const line of resolvedLines) print(line);
+    if (resolvedCount > 0) {
       print("");
-      print(`  ${pc.magenta(pc.bold("brakit"))} ${pc.dim("\u2192")} ${pc.green("Issues fixed!")}`);
+      print(`${prefix} ${pc.green(pluralize(resolvedCount, "issue") + " resolved " + UNICODE_CHECK_MARK)}`);
     }
   });
 }
diff --git a/src/runtime/setup.ts b/src/runtime/setup.ts
index 44895b6..6f2179c 100644
--- a/src/runtime/setup.ts
+++ b/src/runtime/setup.ts
@@ -5,7 +5,7 @@ import { setupErrorHook } from "../instrument/hooks/errors.js";
 import { createDefaultRegistry } from "../instrument/adapters/index.js";
 import { createDashboardHandler } from "../dashboard/router.js";
 import { readFile, mkdir, writeFile } from "node:fs/promises";
-import { existsSync, unlinkSync } from "node:fs";
+import { existsSync, unlinkSync, readFileSync } from "node:fs";
 import { resolve } from "node:path";
 import { EventBus } from "../core/event-bus.js";
 import type { Services } from "../core/services.js";
@@ -22,17 +22,18 @@ import {
   DEFAULT_MAX_BODY_CAPTURE,
   METRICS_DIR,
   PORT_FILE,
-  KNOWN_DEPENDENCY_NAMES,
   EXIT_REASON_SIGINT,
   EXIT_REASON_SIGTERM,
   EXIT_REASON_CLEAN,
   TELEMETRY_EVENT_SETUP_COMPLETED,
   TELEMETRY_EVENT_FIRST_REQUEST,
 } from "../constants/index.js";
+import { KNOWN_DEPENDENCY_NAMES, INSTALLED_HOOKS } from "../constants/detection.js";
 import type {
   TelemetryEvent,
   BrakitConfig,
   Framework,
+  StackDetectionResult,
   TracedFetch,
   TracedLog,
   TracedError,
@@ -46,19 +47,11 @@ import { getErrorMessage } from "../utils/type-guards.js";
 import { getProjectDataDir } from "../utils/fs.js";
 import {
   detectFrameworkFromDeps,
-  detectPackageManagerSync,
+  detectPackageManager,
+  detectConfigFiles,
 } from "../detect/project.js";
-import {
-  initSession,
-  trackSession,
-  trackEvent,
-  recordRequestCount,
-  recordInsightTypes,
-  recordRulesTriggered,
-  recordSetupCompleted,
-  recordFirstRequest,
-  recordExitReason,
-} from "../telemetry/index.js";
+import { detectJsRuntime, extractLoadedPackages } from "../detect/runtime.js";
+import { session, flushSession, trackEvent } from "../telemetry/index.js";
 
 let initPromise: Promise<void> | null = null;
 
@@ -97,12 +90,7 @@ function createStores(bus: EventBus): Stores {
 
 /*  Phase 2 — Install instrumentation hooks                           */
 
-function installHooks(bus: EventBus): {
-  framework: Framework;
-  adapterNames: string[];
-  adaptersFailed: string[];
-  frameworkCandidates: string[];
-} {
+function installHooks(bus: EventBus): StackDetectionResult {
   const telemetryEmit = (event: TelemetryEvent): void => {
     const channel = `telemetry:${event.type}` as keyof ChannelMap;
     bus.emit(channel, event.data as ChannelMap[typeof channel]);
@@ -118,24 +106,27 @@ function installHooks(bus: EventBus): {
   const cwd = process.cwd();
 
   let framework: Framework = "unknown";
-  let frameworkCandidates: string[] = [];
+  let detectedDependencies: string[] = [];
+  let configFilesDetected: string[] = [];
   try {
     const pkg = JSON.parse(
-      require("node:fs").readFileSync(resolve(cwd, "package.json"), "utf-8"),
+      readFileSync(resolve(cwd, "package.json"), "utf-8"),
     );
     const allDeps = { ...pkg.dependencies, ...pkg.devDependencies };
     framework = detectFrameworkFromDeps(allDeps);
-    // Capture which deps were found for telemetry diagnostics (no PII — just package names)
-    frameworkCandidates = KNOWN_DEPENDENCY_NAMES.filter((dep) => dep in allDeps);
+    detectedDependencies = KNOWN_DEPENDENCY_NAMES.filter((dep) => dep in allDeps);
+    configFilesDetected = detectConfigFiles(cwd);
   } catch {
-    /* no package.json */
+    /* no package.json or bundler blocked fs access */
   }
 
   return {
     framework,
     adapterNames: adapterRegistry.getActive().map((a) => a.name),
     adaptersFailed: [...adapterRegistry.getFailed()],
-    frameworkCandidates,
+    detectedDependencies,
+    configFilesDetected,
+    jsRuntime: detectJsRuntime(),
   };
 }
 
@@ -192,14 +183,12 @@ function registerLifecycle(
   const sendTelemetry = (): void => {
     if (telemetrySent) return;
     telemetrySent = true;
-    recordRequestCount(stores.requestStore.getAll().length);
-    recordInsightTypes(
+    session.recordCounts(
+      stores.requestStore.getAll().length,
       services.analysisEngine.getInsights().map((i) => i.type),
-    );
-    recordRulesTriggered(
       services.analysisEngine.getFindings().map((f) => f.rule),
     );
-    trackSession(allServices);
+    flushSession(allServices);
   };
 
   let teardownCalled = false;
@@ -223,11 +212,11 @@ function registerLifecycle(
 
   health.setTeardown(runTeardown);
 
-  process.on("SIGINT", () => { recordExitReason(EXIT_REASON_SIGINT); });
-  process.on("SIGTERM", () => { recordExitReason(EXIT_REASON_SIGTERM); });
+  process.on("SIGINT", () => { session.recordExitReason(EXIT_REASON_SIGINT); });
+  process.on("SIGTERM", () => { session.recordExitReason(EXIT_REASON_SIGTERM); });
   process.on("beforeExit", async () => {
     await drainPendingCaptures();
-    recordExitReason(EXIT_REASON_CLEAN);
+    session.recordExitReason(EXIT_REASON_CLEAN);
     sendTelemetry();
   });
   process.on("exit", () => {
@@ -253,20 +242,22 @@ async function doSetup(): Promise<void> {
   } as Services;
 
   // Phase 2 — instrumentation hooks
-  const { framework, adapterNames, adaptersFailed, frameworkCandidates } = installHooks(bus);
+  const detection = installHooks(bus);
 
-  initSession(framework, detectPackageManagerSync(cwd), false, adapterNames);
+  session.init(detection.framework, detectPackageManager(cwd), false, detection.adapterNames);
 
   const setupDurationMs = Date.now() - setupStart;
-  recordSetupCompleted({ frameworkCandidates, adaptersFailed, setupDurationMs });
+  session.recordSetup(detection, setupDurationMs);
 
   trackEvent(TELEMETRY_EVENT_SETUP_COMPLETED, {
-    framework,
-    framework_detection_candidates: frameworkCandidates,
-    adapters_detected: adapterNames,
-    adapters_failed: adaptersFailed,
-    hooks_installed: ["fetch", "console", "error"],
+    framework: detection.framework,
+    framework_detection_candidates: detection.detectedDependencies,
+    adapters_detected: detection.adapterNames,
+    adapters_failed: detection.adaptersFailed,
+    hooks_installed: [...INSTALLED_HOOKS],
     setup_duration_ms: setupDurationMs,
+    config_files_detected: detection.configFilesDetected,
+    js_runtime: detection.jsRuntime,
   });
 
   // Phase 3 — graph builder
@@ -295,10 +286,15 @@ async function doSetup(): Promise<void> {
     onFirstRequest(port) {
       setBrakitPort(port);
       brakitDebug(`[setup] onFirstRequest fired, port=${port}`);
-      recordFirstRequest();
+
+      const loadedPackages = extractLoadedPackages();
+      session.recordFirstRequest(loadedPackages);
+
       trackEvent(TELEMETRY_EVENT_FIRST_REQUEST, {
         port,
         time_to_first_request_ms: Date.now() - setupStart,
+        loaded_packages: loadedPackages,
+        loaded_package_count: loadedPackages.length,
       });
 
       void (async () => {
diff --git a/src/telemetry/config.ts b/src/telemetry/config.ts
index fbe58ee..dd8cd6e 100644
--- a/src/telemetry/config.ts
+++ b/src/telemetry/config.ts
@@ -14,10 +14,21 @@ export interface TelemetryConfig {
 const CONFIG_DIR = join(homedir(), ".brakit");
 const CONFIG_PATH = join(CONFIG_DIR, "config.json");
 
+function isValidTelemetryConfig(value: unknown): value is TelemetryConfig {
+  return (
+    typeof value === "object" &&
+    value !== null &&
+    typeof (value as TelemetryConfig).telemetry === "boolean" &&
+    typeof (value as TelemetryConfig).anonymousId === "string" &&
+    (value as TelemetryConfig).anonymousId.length > 0
+  );
+}
+
 export function readConfig(): TelemetryConfig | null {
   try {
     if (!existsSync(CONFIG_PATH)) return null;
-    return JSON.parse(readFileSync(CONFIG_PATH, "utf-8")) as TelemetryConfig;
+    const parsed: unknown = JSON.parse(readFileSync(CONFIG_PATH, "utf-8"));
+    return isValidTelemetryConfig(parsed) ? parsed : null;
   } catch {
     return null;
   }
@@ -42,9 +53,7 @@ export function writeConfig(config: TelemetryConfig): void {
 
 export function getOrCreateConfig(): TelemetryConfig {
   const existing = readConfig();
-  if (existing && typeof existing.telemetry === "boolean" && existing.anonymousId) {
-    return existing;
-  }
+  if (existing) return existing;
   const config: TelemetryConfig = { telemetry: true, anonymousId: randomUUID() };
   writeConfig(config);
   return config;
@@ -56,7 +65,8 @@ export function isTelemetryEnabled(): boolean {
   if (cachedEnabled !== null) return cachedEnabled;
   const env = process.env.BRAKIT_TELEMETRY;
   if (env !== undefined) {
-    cachedEnabled = env !== "false" && env !== "0" && env !== "off";
+    const normalized = env.toLowerCase().trim();
+    cachedEnabled = normalized !== "false" && normalized !== "0" && normalized !== "off";
     return cachedEnabled;
   }
   cachedEnabled = readConfig()?.telemetry ?? true;
diff --git a/src/telemetry/index.ts b/src/telemetry/index.ts
index 350cb94..f6e2ceb 100644
--- a/src/telemetry/index.ts
+++ b/src/telemetry/index.ts
@@ -1,173 +1,15 @@
-import { platform, release, arch } from "node:os";
-import { spawn } from "node:child_process";
-import { VERSION } from "../index.js";
-import type { Services } from "../core/services.js";
-import { readConfig, getOrCreateConfig, isTelemetryEnabled } from "./config.js";
-import {
-  POSTHOG_HOST,
-  POSTHOG_CAPTURE_PATH,
-  POSTHOG_REQUEST_TIMEOUT_MS,
-  SPEED_BUCKET_THRESHOLDS,
-} from "../constants/labels.js";
-import {
-  TELEMETRY_EVENT_DASHBOARD_VIEWED,
-  TELEMETRY_EVENT_SESSION,
-  TELEMETRY_EVENT_GRAPH_FEATURE,
-} from "../constants/config.js";
-
 export { isTelemetryEnabled, setTelemetryEnabled } from "./config.js";
+export { trackEvent } from "./transport.js";
+export { Session } from "./session.js";
+export type { PythonStackInfo } from "./session.js";
 
-const POSTHOG_KEY: string = process.env.POSTHOG_API_KEY ?? "";
-
-// Common properties shared across all events
-
-function commonProperties(): Record<string, unknown> {
-  return {
-    brakit_version: VERSION,
-    node_version: process.version,
-    os: `${platform()}-${release()}`,
-    arch: arch(),
-    $lib: "brakit",
-    $process_person_profile: false,
-    $geoip_disable: true,
-  };
-}
-
-// Lightweight event tracking — fire-and-forget via detached child process
-
-function sendToPosthog(
-  event: string,
-  properties: Record<string, unknown>,
-): void {
-  if (!isTelemetryEnabled()) return;
-
-  const config = getOrCreateConfig();
-  const payload = {
-    api_key: POSTHOG_KEY,
-    event,
-    distinct_id: config.anonymousId,
-    timestamp: new Date().toISOString(),
-    properties: { ...commonProperties(), ...properties },
-  };
-
-  try {
-    const body = JSON.stringify(payload);
-    const url = `${POSTHOG_HOST}${POSTHOG_CAPTURE_PATH}`;
-    const child = spawn(
-      process.execPath,
-      [
-        "-e",
-        `fetch(${JSON.stringify(url)},{method:"POST",headers:{"content-type":"application/json"},body:${JSON.stringify(body)},signal:AbortSignal.timeout(${POSTHOG_REQUEST_TIMEOUT_MS})}).catch(()=>{})`,
-      ],
-      { detached: true, stdio: "ignore" },
-    );
-    child.unref();
-  } catch {
-    /* non-critical */
-  }
-}
-
-/**
- * Track a lightweight event. Use for journey milestones (cli_invoked,
- * setup_completed, first_request, dashboard_viewed, cli_uninstall).
- * Never blocks the host app.
- */
-export function trackEvent(
-  event: string,
-  properties: Record<string, unknown>,
-): void {
-  sendToPosthog(event, { sdk: "node", ...properties });
-}
-
-// Session state — accumulated during the session, sent on exit
-
-interface SessionState {
-  startTime: number;
-  framework: string;
-  packageManager: string;
-  isCustomCommand: boolean;
-  adapters: string[];
-  requestCount: number;
-  insightTypes: Set<string>;
-  rulesTriggered: Set<string>;
-  tabsViewed: Set<string>;
-  dashboardOpened: boolean;
-  explainUsed: boolean;
-  frameworkCandidates: string[];
-  adaptersFailed: string[];
-  setupDurationMs: number;
-  setupSucceeded: boolean;
-  firstRequestAt: number;
-  dashboardOpenedAt: number;
-  exitReason: string;
-}
-
-const session: SessionState = {
-  startTime: 0,
-  framework: "",
-  packageManager: "",
-  isCustomCommand: false,
-  adapters: [],
-  requestCount: 0,
-  insightTypes: new Set(),
-  rulesTriggered: new Set(),
-  tabsViewed: new Set(),
-  dashboardOpened: false,
-  explainUsed: false,
-  frameworkCandidates: [],
-  adaptersFailed: [],
-  setupDurationMs: 0,
-  setupSucceeded: false,
-  firstRequestAt: 0,
-  dashboardOpenedAt: 0,
-  exitReason: "unknown",
-};
-
-export function initSession(
-  framework: string,
-  packageManager: string,
-  isCustomCommand: boolean,
-  adapters: string[],
-): void {
-  getOrCreateConfig();
-
-  session.startTime = Date.now();
-  session.framework = framework;
-  session.packageManager = packageManager;
-  session.isCustomCommand = isCustomCommand;
-  session.adapters = adapters;
-}
-
-export function recordRequestCount(count: number): void {
-  session.requestCount = count;
-}
-
-export function recordInsightTypes(types: string[]): void {
-  for (const t of types) session.insightTypes.add(t);
-}
-
-export function recordRulesTriggered(rules: string[]): void {
-  for (const r of rules) session.rulesTriggered.add(r);
-}
-
-export function recordTabViewed(tab: string): void {
-  session.tabsViewed.add(tab);
-}
-
-export function recordDashboardOpened(): void {
-  if (session.dashboardOpened) return; // Only track first open
-  session.dashboardOpened = true;
-  session.dashboardOpenedAt = Date.now();
-  trackEvent(TELEMETRY_EVENT_DASHBOARD_VIEWED, {
-    time_to_dashboard_ms:
-      session.startTime > 0 ? Date.now() - session.startTime : null,
-    request_count_at_open: session.requestCount,
-  });
-}
+import { Session } from "./session.js";
+import { TELEMETRY_EVENT_GRAPH_FEATURE } from "../constants/telemetry.js";
+import { isTelemetryEnabled } from "./config.js";
+import { trackEvent } from "./transport.js";
 
-export function recordExplainUsed(): void {
-  session.explainUsed = true;
-}
+/** Singleton session instance. Created once per process. */
+export const session = new Session();
 
 export function recordGraphFeature(feature: string, detail?: string): void {
   trackEvent(TELEMETRY_EVENT_GRAPH_FEATURE, {
@@ -176,95 +18,7 @@ export function recordGraphFeature(feature: string, detail?: string): void {
   });
 }
 
-export function recordSetupCompleted(info: {
-  frameworkCandidates: string[];
-  adaptersFailed: string[];
-  setupDurationMs: number;
-}): void {
-  session.frameworkCandidates = info.frameworkCandidates;
-  session.adaptersFailed = info.adaptersFailed;
-  session.setupDurationMs = info.setupDurationMs;
-  session.setupSucceeded = true;
-}
-
-export function recordFirstRequest(): void {
-  if (!session.firstRequestAt) session.firstRequestAt = Date.now();
-}
-
-export function recordExitReason(reason: string): void {
-  if (session.exitReason === "unknown") session.exitReason = reason;
-}
-
-// Session event — fired on process exit with full session summary
-
-function speedBucket(ms: number): string {
-  if (ms === 0) return "none";
-  const t = SPEED_BUCKET_THRESHOLDS;
-  if (ms < t[0]) return `<${t[0]}ms`;
-  for (let i = 1; i < t.length; i++) {
-    if (ms < t[i]) return `${t[i - 1]}-${t[i]}ms`;
-  }
-  return `>${t[t.length - 1]}ms`;
-}
-
-export function trackSession(services: Services): void {
+export function flushSession(services: Parameters<Session["flush"]>[0]): void {
   if (!isTelemetryEnabled()) return;
-
-  const isFirstSession = readConfig() === null;
-  const metricsStore = services.metricsStore;
-  const analysisEngine = services.analysisEngine;
-  const live = metricsStore.getLiveEndpoints();
-  const insights = analysisEngine.getInsights();
-  const findings = analysisEngine.getFindings();
-
-  let totalRequests = 0;
-  let totalDuration = 0;
-  let slowestP95 = 0;
-
-  for (const ep of live) {
-    totalRequests += ep.summary.totalRequests;
-    totalDuration += ep.summary.p95Ms * ep.summary.totalRequests;
-    if (ep.summary.p95Ms > slowestP95) slowestP95 = ep.summary.p95Ms;
-  }
-
-  const now = Date.now();
-  sendToPosthog(TELEMETRY_EVENT_SESSION, {
-    sdk: "node",
-    framework: session.framework,
-    package_manager: session.packageManager,
-    is_custom_command: session.isCustomCommand,
-    first_session: isFirstSession,
-    adapters_detected: session.adapters,
-    request_count: session.requestCount,
-    error_count: services.errorStore.getAll().length,
-    query_count: services.queryStore.getAll().length,
-    fetch_count: services.fetchStore.getAll().length,
-    insight_count: insights.length,
-    finding_count: findings.length,
-    insight_types: [...session.insightTypes],
-    rules_triggered: [...session.rulesTriggered],
-    endpoint_count: live.length,
-    avg_duration_ms:
-      totalRequests > 0 ? Math.round(totalDuration / totalRequests) : 0,
-    slowest_endpoint_bucket: speedBucket(slowestP95),
-    tabs_viewed: [...session.tabsViewed],
-    dashboard_opened: session.dashboardOpened,
-    explain_used: session.explainUsed,
-    session_duration_s: Math.ceil((now - session.startTime) / 1000),
-    session_duration_ms: now - session.startTime,
-    setup_succeeded: session.setupSucceeded,
-    setup_duration_ms: session.setupDurationMs,
-    framework_detection_candidates: session.frameworkCandidates,
-    adapters_failed: session.adaptersFailed,
-    time_to_first_request_ms: session.firstRequestAt
-      ? session.firstRequestAt - session.startTime
-      : null,
-    time_to_dashboard_ms: session.dashboardOpenedAt
-      ? session.dashboardOpenedAt - session.startTime
-      : null,
-    exit_reason: session.exitReason,
-  });
-
-  // Ensure config file exists (creates anonymousId if needed)
-  getOrCreateConfig();
+  session.flush(services);
 }
diff --git a/src/telemetry/session.ts b/src/telemetry/session.ts
new file mode 100644
index 0000000..f14688b
--- /dev/null
+++ b/src/telemetry/session.ts
@@ -0,0 +1,229 @@
+import type { Services } from "../core/services.js";
+import type { Framework, JsRuntime, ExitReason, StackDetectionResult } from "../types/index.js";
+import {
+  SPEED_BUCKET_THRESHOLDS,
+  TELEMETRY_EVENT_SESSION,
+  TELEMETRY_EVENT_DASHBOARD_VIEWED,
+  TELEMETRY_SDK_NAME,
+} from "../constants/telemetry.js";
+import { readConfig, getOrCreateConfig } from "./config.js";
+import { sendToPosthog, trackEvent } from "./transport.js";
+
+export interface TelemetryTransport {
+  send: typeof sendToPosthog;
+  track: typeof trackEvent;
+}
+
+export interface PythonStackInfo {
+  framework: string;
+  adapters: string[];
+  pythonVersion: string;
+}
+
+const defaultTransport: TelemetryTransport = { send: sendToPosthog, track: trackEvent };
+
+export class Session {
+  private readonly transport: TelemetryTransport;
+
+  constructor(transport: TelemetryTransport = defaultTransport) {
+    this.transport = transport;
+  }
+
+  // ── Setup phase ──
+  private startTime = 0;
+  private framework: Framework = "unknown";
+  private packageManager = "";
+  private isCustomCommand = false;
+  private adapters: string[] = [];
+  private setupDurationMs = 0;
+  private setupSucceeded = false;
+
+  // ── Detection ──
+  private detectedDependencies: string[] = [];
+  private adaptersFailed: string[] = [];
+  private configFilesDetected: string[] = [];
+  private jsRuntime: JsRuntime = "node";
+  private loadedPackages: string[] = [];
+
+  // ── Python SDK ──
+  private pythonConnected = false;
+  private pythonFramework = "unknown";
+  private pythonAdapters: string[] = [];
+  private pythonVersion = "";
+
+  // ── Runtime accumulation ──
+  private requestCount = 0;
+  private insightTypes = new Set<string>();
+  private rulesTriggered = new Set<string>();
+  private tabsViewed = new Set<string>();
+  private dashboardOpened = false;
+  private explainUsed = false;
+  private firstRequestAt = 0;
+  private dashboardOpenedAt = 0;
+  private exitReason: ExitReason = "unknown";
+
+  // ── Setup phase ──
+
+  init(
+    framework: Framework,
+    packageManager: string,
+    isCustomCommand: boolean,
+    adapters: string[],
+  ): void {
+    getOrCreateConfig();
+    this.startTime = Date.now();
+    this.framework = framework;
+    this.packageManager = packageManager;
+    this.isCustomCommand = isCustomCommand;
+    this.adapters = adapters;
+  }
+
+  recordSetup(detection: StackDetectionResult, durationMs: number): void {
+    this.detectedDependencies = detection.detectedDependencies;
+    this.adaptersFailed = detection.adaptersFailed;
+    this.configFilesDetected = detection.configFilesDetected;
+    this.jsRuntime = detection.jsRuntime;
+    this.setupDurationMs = durationMs;
+    this.setupSucceeded = true;
+  }
+
+  // ── Runtime events ──
+
+  recordFirstRequest(loadedPackages: string[]): void {
+    if (!this.firstRequestAt) this.firstRequestAt = Date.now();
+    this.loadedPackages = loadedPackages;
+  }
+
+  recordPythonStack(info: PythonStackInfo): void {
+    this.pythonConnected = true;
+    this.pythonFramework = info.framework;
+    this.pythonAdapters = info.adapters;
+    this.pythonVersion = info.pythonVersion;
+  }
+
+  recordDashboardOpened(): void {
+    if (this.dashboardOpened) return;
+    this.dashboardOpened = true;
+    this.dashboardOpenedAt = Date.now();
+    this.transport.track(TELEMETRY_EVENT_DASHBOARD_VIEWED, {
+      time_to_dashboard_ms:
+        this.startTime > 0 ? Date.now() - this.startTime : null,
+      request_count_at_open: this.requestCount,
+    });
+  }
+
+  recordTabViewed(tab: string): void {
+    this.tabsViewed.add(tab);
+  }
+
+  recordExplainUsed(): void {
+    this.explainUsed = true;
+  }
+
+  recordExitReason(reason: ExitReason): void {
+    if (this.exitReason === "unknown") this.exitReason = reason;
+  }
+
+  // ── Pre-flush snapshot from services ──
+
+  recordCounts(requestCount: number, insightTypes: string[], rulesTriggered: string[]): void {
+    this.requestCount = requestCount;
+    for (const t of insightTypes) this.insightTypes.add(t);
+    for (const r of rulesTriggered) this.rulesTriggered.add(r);
+  }
+
+  // ── Serialization ──
+
+  /** Build the full PostHog session payload. Single source of truth for all fields. */
+  toPostHogPayload(services: Services): Record<string, unknown> {
+    const metricsStore = services.metricsStore;
+    const analysisEngine = services.analysisEngine;
+    const live = metricsStore.getLiveEndpoints();
+    const insights = analysisEngine.getInsights();
+    const findings = analysisEngine.getFindings();
+
+    let totalRequests = 0;
+    let totalDuration = 0;
+    let slowestP95 = 0;
+    for (const ep of live) {
+      totalRequests += ep.summary.totalRequests;
+      totalDuration += ep.summary.p95Ms * ep.summary.totalRequests;
+      if (ep.summary.p95Ms > slowestP95) slowestP95 = ep.summary.p95Ms;
+    }
+
+    const now = Date.now();
+    return {
+      sdk: TELEMETRY_SDK_NAME,
+
+      // Stack detection
+      framework: this.framework,
+      package_manager: this.packageManager,
+      js_runtime: this.jsRuntime,
+      framework_detection_candidates: this.detectedDependencies,
+      config_files_detected: this.configFilesDetected,
+      loaded_packages: this.loadedPackages,
+      loaded_package_count: this.loadedPackages.length,
+      adapters_detected: this.adapters,
+      adapters_failed: this.adaptersFailed,
+
+      // Python SDK
+      python_connected: this.pythonConnected,
+      python_framework: this.pythonFramework,
+      python_adapters: this.pythonAdapters,
+      python_version: this.pythonVersion,
+
+      // Session metadata
+      is_custom_command: this.isCustomCommand,
+      first_session: readConfig() === null,
+      setup_succeeded: this.setupSucceeded,
+      setup_duration_ms: this.setupDurationMs,
+      session_duration_s: Math.ceil((now - this.startTime) / 1000),
+      session_duration_ms: now - this.startTime,
+      exit_reason: this.exitReason,
+
+      // Usage
+      request_count: this.requestCount,
+      error_count: services.errorStore.getAll().length,
+      query_count: services.queryStore.getAll().length,
+      fetch_count: services.fetchStore.getAll().length,
+      endpoint_count: live.length,
+      avg_duration_ms:
+        totalRequests > 0 ? Math.round(totalDuration / totalRequests) : 0,
+      slowest_endpoint_bucket: speedBucket(slowestP95),
+
+      // Analysis
+      insight_count: insights.length,
+      finding_count: findings.length,
+      insight_types: [...this.insightTypes],
+      rules_triggered: [...this.rulesTriggered],
+
+      // Dashboard engagement
+      tabs_viewed: [...this.tabsViewed],
+      dashboard_opened: this.dashboardOpened,
+      explain_used: this.explainUsed,
+
+      // Timing
+      time_to_first_request_ms: this.firstRequestAt
+        ? this.firstRequestAt - this.startTime
+        : null,
+      time_to_dashboard_ms: this.dashboardOpenedAt
+        ? this.dashboardOpenedAt - this.startTime
+        : null,
+    };
+  }
+
+  flush(services: Services): void {
+    this.transport.send(TELEMETRY_EVENT_SESSION, this.toPostHogPayload(services));
+    getOrCreateConfig();
+  }
+}
+
+export function speedBucket(ms: number): string {
+  if (ms === 0) return "none";
+  const t = SPEED_BUCKET_THRESHOLDS;
+  if (ms < t[0]) return `<${t[0]}ms`;
+  for (let i = 1; i < t.length; i++) {
+    if (ms < t[i]) return `${t[i - 1]}-${t[i]}ms`;
+  }
+  return `>${t[t.length - 1]}ms`;
+}
diff --git a/src/telemetry/transport.ts b/src/telemetry/transport.ts
new file mode 100644
index 0000000..b6b8416
--- /dev/null
+++ b/src/telemetry/transport.ts
@@ -0,0 +1,67 @@
+import { platform, release, arch } from "node:os";
+import { spawn } from "node:child_process";
+import { VERSION } from "../index.js";
+import {
+  POSTHOG_HOST,
+  POSTHOG_CAPTURE_PATH,
+  POSTHOG_REQUEST_TIMEOUT_MS,
+  TELEMETRY_SDK_NAME,
+} from "../constants/telemetry.js";
+import { getOrCreateConfig, isTelemetryEnabled } from "./config.js";
+import { brakitDebug } from "../utils/log.js";
+
+const POSTHOG_KEY: string = process.env.POSTHOG_API_KEY ?? "";
+
+function commonProperties(): Record<string, unknown> {
+  return {
+    brakit_version: VERSION,
+    node_version: process.version,
+    os: `${platform()}-${release()}`,
+    arch: arch(),
+    $lib: "brakit",
+    $process_person_profile: false,
+    $geoip_disable: true,
+  };
+}
+
+/** Fire-and-forget event delivery via detached child process. Never blocks the host app. */
+export function sendToPosthog(
+  event: string,
+  properties: Record<string, unknown>,
+): void {
+  if (!isTelemetryEnabled() || !POSTHOG_KEY) return;
+
+  const config = getOrCreateConfig();
+  const payload = {
+    api_key: POSTHOG_KEY,
+    event,
+    distinct_id: config.anonymousId,
+    timestamp: new Date().toISOString(),
+    properties: { ...commonProperties(), ...properties },
+  };
+
+  try {
+    const serializedPayload = JSON.stringify(payload);
+    const url = `${POSTHOG_HOST}${POSTHOG_CAPTURE_PATH}`;
+    // Safety: JSON.stringify guarantees valid string literals — url is a constant and
+    // serializedPayload contains only JSON-safe characters, so eval injection is not possible.
+    const child = spawn(
+      process.execPath,
+      [
+        "-e",
+        `fetch(${JSON.stringify(url)},{method:"POST",headers:{"content-type":"application/json"},body:${JSON.stringify(serializedPayload)},signal:AbortSignal.timeout(${POSTHOG_REQUEST_TIMEOUT_MS})}).catch(()=>{})`,
+      ],
+      { detached: true, stdio: "ignore" },
+    );
+    child.unref();
+  } catch (err) {
+    brakitDebug(`telemetry send failed: ${err}`);
+  }
+}
+
+export function trackEvent(
+  event: string,
+  properties: Record<string, unknown>,
+): void {
+  sendToPosthog(event, { sdk: TELEMETRY_SDK_NAME, ...properties });
+}
diff --git a/src/types/api-contracts.ts b/src/types/api-contracts.ts
index 86e32c6..61a7c42 100644
--- a/src/types/api-contracts.ts
+++ b/src/types/api-contracts.ts
@@ -58,7 +58,7 @@ export interface LiveMetricsResponse {
   endpoints: LiveEndpointData[];
 }
 
-export type SDKEventType = "request" | "db.query" | "fetch" | "log" | "error" | "auth.check";
+export type SDKEventType = "request" | "db.query" | "fetch" | "log" | "error" | "auth.check" | "sdk.hello";
 
 export interface SDKEvent {
   type: SDKEventType;
diff --git a/src/types/detection.ts b/src/types/detection.ts
new file mode 100644
index 0000000..518eae5
--- /dev/null
+++ b/src/types/detection.ts
@@ -0,0 +1,16 @@
+import type { Framework } from "./config.js";
+
+export type JsRuntime = "node" | "bun" | "deno";
+
+export type ExitReason = "clean" | "sigint" | "sigterm" | "unknown";
+
+export type HookName = "fetch" | "console" | "error";
+
+export interface StackDetectionResult {
+  framework: Framework;
+  detectedDependencies: string[];
+  configFilesDetected: string[];
+  jsRuntime: JsRuntime;
+  adapterNames: string[];
+  adaptersFailed: string[];
+}
diff --git a/src/types/index.ts b/src/types/index.ts
index 7f57ed4..d283ae8 100644
--- a/src/types/index.ts
+++ b/src/types/index.ts
@@ -58,3 +58,10 @@ export type {
   StatefulIssue,
   IssuesData,
 } from "./issue-lifecycle.js";
+
+export type {
+  JsRuntime,
+  ExitReason,
+  HookName,
+  StackDetectionResult,
+} from "./detection.js";
diff --git a/tests/output/terminal.test.ts b/tests/output/terminal.test.ts
index 43478be..71cfbfc 100644
--- a/tests/output/terminal.test.ts
+++ b/tests/output/terminal.test.ts
@@ -1,8 +1,9 @@
-import { describe, it, expect, vi, beforeEach, afterEach } from "vitest";
+import { describe, it, expect, vi, beforeEach, afterEach, type MockInstance } from "vitest";
 import { printBanner, startTerminalInsights } from "../../src/output/terminal.js";
 import { makeInsight, makeStatefulIssue, makeAnalysisUpdate } from "../helpers/factories.js";
 import { EventBus } from "../../src/core/event-bus.js";
 import type { Services } from "../../src/core/services.js";
+import { DASHBOARD_PREFIX } from "../../src/constants/index.js";
 
 describe("printBanner", () => {
   it("prints proxy, target, and dashboard URLs", () => {
@@ -11,14 +12,13 @@ describe("printBanner", () => {
     const output = spy.mock.calls.map((c) => c[0]).join("");
     expect(output).toContain("localhost:3000");
     expect(output).toContain("localhost:3001");
-    expect(output).toContain("/__brakit");
+    expect(output).toContain(DASHBOARD_PREFIX);
     spy.mockRestore();
   });
 });
 
 describe("startTerminalInsights", () => {
-  // eslint-disable-next-line @typescript-eslint/no-explicit-any
-  let spy: any;
+  let spy: MockInstance;
   let bus: EventBus;
   let services: Services;
 
@@ -36,7 +36,7 @@ describe("startTerminalInsights", () => {
         start: vi.fn(),
         stop: vi.fn(),
       },
-    } as any;
+    } as unknown as Services;
   });
 
   afterEach(() => {
@@ -47,12 +47,15 @@ describe("startTerminalInsights", () => {
     return spy.mock.calls.map((c: unknown[]) => c[0]).join("");
   }
 
-  it("prints warning and critical issues to stdout", () => {
+  it("prints summary line for new issues", () => {
     const dispose = startTerminalInsights(services, 3000);
     const issues = [makeStatefulIssue({ severity: "warning", title: "Slow Endpoint" })];
     bus.emit("analysis:updated", makeAnalysisUpdate([makeInsight({ severity: "warning", title: "Slow Endpoint" })], [], issues));
     const output = getOutput();
-    expect(output).toContain("Slow Endpoint");
+    expect(output).toContain("1 new issue");
+    expect(output).toContain(DASHBOARD_PREFIX);
+    expect(output).toContain("Fix brakit findings");
+    expect(output).not.toContain("Slow Endpoint");
     dispose();
   });
 
@@ -71,7 +74,7 @@ describe("startTerminalInsights", () => {
 
     bus.emit("analysis:updated", update);
     const firstOutput = getOutput();
-    expect(firstOutput).toContain("Slow Endpoint");
+    expect(firstOutput).toContain("1 new issue");
 
     spy.mockClear();
     bus.emit("analysis:updated", update);
@@ -85,4 +88,45 @@ describe("startTerminalInsights", () => {
     expect(getOutput()).toBe("");
     dispose();
   });
+
+  it("summarizes multiple issues as a count", () => {
+    const dispose = startTerminalInsights(services, 3000);
+    const issues = [
+      makeStatefulIssue({ severity: "warning", title: "Issue A", rule: "rule-a" }),
+      makeStatefulIssue({ severity: "critical", title: "Issue B", rule: "rule-b" }),
+      makeStatefulIssue({ severity: "warning", title: "Issue C", rule: "rule-c" }),
+    ];
+    bus.emit("analysis:updated", makeAnalysisUpdate([], [], issues));
+    const output = getOutput();
+    expect(output).toContain("3 new issues");
+    expect(output).not.toContain("Issue A");
+    expect(output).not.toContain("Issue B");
+    expect(output).not.toContain("Issue C");
+    dispose();
+  });
+
+  it("shows compact resolved summary", () => {
+    const dispose = startTerminalInsights(services, 3000);
+    const issues = [
+      makeStatefulIssue({ severity: "warning", title: "Fixed" }, { state: "resolved" }),
+      makeStatefulIssue({ severity: "warning", title: "Fixed 2", rule: "rule-2" }, { state: "resolved" }),
+    ];
+    bus.emit("analysis:updated", makeAnalysisUpdate([], [], issues));
+    const output = getOutput();
+    expect(output).toContain("2 issues resolved");
+    expect(output).not.toContain("Fixed");
+    dispose();
+  });
+
+  it("shows compact regressed summary", () => {
+    const dispose = startTerminalInsights(services, 3000);
+    const issues = [
+      makeStatefulIssue({ severity: "warning", title: "Regressed" }, { state: "regressed" }),
+    ];
+    bus.emit("analysis:updated", makeAnalysisUpdate([], [], issues));
+    const output = getOutput();
+    expect(output).toContain("1 issue regressed");
+    expect(output).toContain(DASHBOARD_PREFIX);
+    dispose();
+  });
 });