diff --git a/.gitignore b/.gitignore
index c7512e8..ac735e9 100644
--- a/.gitignore
+++ b/.gitignore
@@ -5,3 +5,5 @@ coverage/
 .DS_Store
 .env
 .env.*
+**/.env.braintrust
+**/.braintrust.json
diff --git a/packages/spark/src/braintrust-cli.ts b/packages/spark/src/braintrust-cli.ts
index 1855c7c..d2aa55d 100644
--- a/packages/spark/src/braintrust-cli.ts
+++ b/packages/spark/src/braintrust-cli.ts
@@ -17,6 +17,10 @@ export type BraintrustCliContext = {
   readonly project?: string;
 };
 
+export type BraintrustCliUpdateCheck = {
+  readonly upToDate: boolean;
+};
+
 export type BraintrustCliConfigureArgs = {
   readonly apiKey: string;
   readonly apiUrl: string;
@@ -28,6 +32,9 @@ export type BraintrustCliConfigureArgs = {
 export type BraintrustCliRuntime = {
   readonly discover: () => Promise<BraintrustCliDiscovery>;
   readonly install: () => Promise<void>;
+  readonly checkForUpdate: (
+    commandPath: string,
+  ) => Promise<BraintrustCliUpdateCheck>;
   readonly update: (commandPath: string) => Promise<void>;
   readonly status: (commandPath: string) => Promise<BraintrustCliContext>;
   readonly loginAndSwitch: (
@@ -114,6 +121,20 @@ export function createBraintrustCliRuntime(
       await execChecked("Braintrust CLI install", spec, exec);
     },
 
+    async checkForUpdate(commandPath) {
+      const result = await exec({
+        command: commandPath,
+        args: ["self", "update", "--check", "--json"],
+        env,
+      });
+      if (result.exitCode !== 0) {
+        throw new Error(
+          `Braintrust CLI update check failed with exit code ${result.exitCode}. ${summarizeCommandOutput(result)}`.trim(),
+        );
+      }
+      return parseUpdateCheckJson(result.stdout);
+    },
+
     async update(commandPath) {
       await execChecked(
         "Braintrust CLI update",
@@ -282,6 +303,25 @@ async function executableExists(path: string): Promise<boolean> {
   );
 }
 
+function parseUpdateCheckJson(stdout: string): BraintrustCliUpdateCheck {
+  let parsed: unknown;
+  try {
+    parsed = JSON.parse(stdout);
+  } catch {
+    throw new Error("Braintrust CLI update check returned invalid JSON.");
+  }
+  if (!parsed || typeof parsed !== "object") {
+    throw new Error("Braintrust CLI update check returned invalid JSON.");
+  }
+  const upToDate = (parsed as Record<string, unknown>)["up_to_date"];
+  if (typeof upToDate !== "boolean") {
+    throw new Error(
+      "Braintrust CLI update check response was missing the `up_to_date` field.",
+    );
+  }
+  return { upToDate };
+}
+
 function parseStatusJson(stdout: string): BraintrustCliContext {
   let parsed: unknown;
   try {
diff --git a/packages/spark/src/clack-copy.ts b/packages/spark/src/clack-copy.ts
index b896875..27fe427 100644
--- a/packages/spark/src/clack-copy.ts
+++ b/packages/spark/src/clack-copy.ts
@@ -65,7 +65,6 @@ export const CLACK_WIZARD_COPY = {
   },
 
   braintrustCli: {
-    installedVersionUnknown: "version unknown",
     installQuestion: "Install Braintrust CLI?",
     installChoices: {
       yes: {
@@ -122,7 +121,7 @@ export const CLACK_WIZARD_COPY = {
   },
 
   instrumentation: {
-    modeQuestion: "How do you want to add Braintrust instrumentation?",
+    modeQuestion: "How do you want to add Braintrust to your application?",
     modes: {
       builtIn: {
         label: "Use built-in coding agent",
diff --git a/packages/spark/src/clack-wizard.ts b/packages/spark/src/clack-wizard.ts
index 3e26953..00905a8 100644
--- a/packages/spark/src/clack-wizard.ts
+++ b/packages/spark/src/clack-wizard.ts
@@ -394,22 +394,36 @@ async function handleBraintrustCliSetup(
   let commandPath = discovery.commandPath;
 
   if (discovery.installed) {
-    const shouldUpdate = await selectBoolean({
-      message: COPY.braintrustCli.updateQuestion,
-      choices: COPY.braintrustCli.updateChoices,
-      yesFirst: true,
-    });
-    if (shouldUpdate && commandPath) {
-      spinner.update(COPY.braintrustCli.updating);
+    if (commandPath) {
+      let upToDate: boolean;
       try {
-        await deps.braintrustCli.update(commandPath);
-        discovery = await deps.braintrustCli.discover();
-        commandPath = discovery.commandPath ?? commandPath;
-      } catch (error) {
-        spinner.clear();
-        clack.log.warn(
-          COPY.braintrustCli.updateFailed(summarizeBraintrustCliError(error)),
-        );
+        const check = await deps.braintrustCli.checkForUpdate(commandPath);
+        upToDate = check.upToDate;
+      } catch {
+        upToDate = false;
+      }
+
+      if (!upToDate) {
+        const shouldUpdate = await selectBoolean({
+          message: COPY.braintrustCli.updateQuestion,
+          choices: COPY.braintrustCli.updateChoices,
+          yesFirst: true,
+        });
+        if (shouldUpdate) {
+          spinner.update(COPY.braintrustCli.updating);
+          try {
+            await deps.braintrustCli.update(commandPath);
+            discovery = await deps.braintrustCli.discover();
+            commandPath = discovery.commandPath ?? commandPath;
+          } catch (error) {
+            spinner.clear();
+            clack.log.warn(
+              COPY.braintrustCli.updateFailed(
+                summarizeBraintrustCliError(error),
+              ),
+            );
+          }
+        }
       }
     }
   } else {
diff --git a/packages/spark/test/braintrust-cli.test.ts b/packages/spark/test/braintrust-cli.test.ts
index f539697..48d7d01 100644
--- a/packages/spark/test/braintrust-cli.test.ts
+++ b/packages/spark/test/braintrust-cli.test.ts
@@ -37,6 +37,36 @@ describe("Braintrust CLI runtime", () => {
     ]);
   });
 
+  it("builds the update command", async () => {
+    const calls: Array<{
+      readonly command: string;
+      readonly args: readonly string[];
+      readonly env?: NodeJS.ProcessEnv;
+    }> = [];
+    const runtime = createBraintrustCliRuntime({
+      env: { PATH: "/usr/bin" },
+      exec: (spec) => {
+        calls.push(spec);
+        return Promise.resolve({
+          exitCode: 0,
+          signal: null,
+          stdout: "",
+          stderr: "",
+        });
+      },
+    });
+
+    await runtime.update("/usr/local/bin/bt");
+
+    expect(calls).toEqual([
+      {
+        command: "/usr/local/bin/bt",
+        args: ["self", "update"],
+        env: { PATH: "/usr/bin" },
+      },
+    ]);
+  });
+
   it("passes the API key only through env when configuring auth and context", async () => {
     const calls: Array<{
       readonly command: string;
diff --git a/packages/spark/test/clack-wizard.test.ts b/packages/spark/test/clack-wizard.test.ts
index 5263918..57babe3 100644
--- a/packages/spark/test/clack-wizard.test.ts
+++ b/packages/spark/test/clack-wizard.test.ts
@@ -21,6 +21,7 @@ import {
   type BraintrustCliDiscovery,
   type BraintrustCliContext,
   type BraintrustCliRuntime,
+  type BraintrustCliUpdateCheck,
 } from "../src/braintrust-cli";
 import {
   type CodingToolRuntime,
@@ -195,7 +196,7 @@ const WIZARD_INTRO = "Braintrust Setup Wizard";
 const WIZARD_CANCEL_MESSAGE = "Wizard cancelled.";
 const ACCOUNT_QUESTION = "Do you already have a Braintrust account?";
 const INSTRUMENTATION_MODE_MESSAGE =
-  "How do you want to add Braintrust instrumentation?";
+  "How do you want to add Braintrust to your application?";
 const CLI_INSTALL_MESSAGE = "Install Braintrust CLI?";
 const CLI_UPDATE_MESSAGE = "Update Braintrust CLI to the latest version?";
 const TOOL_SELECT_MESSAGE = "Which coding agent should Braintrust Setup use?";
@@ -388,6 +389,9 @@ function createBraintrustCliStub(
   args: {
     readonly discoveries?: readonly BraintrustCliDiscovery[];
     readonly install?: () => Promise<void>;
+    readonly checkForUpdate?: (
+      commandPath: string,
+    ) => Promise<BraintrustCliUpdateCheck>;
     readonly update?: (commandPath: string) => Promise<void>;
     readonly status?: (commandPath: string) => Promise<BraintrustCliContext>;
     readonly loginAndSwitch?: (
@@ -407,6 +411,8 @@ function createBraintrustCliStub(
       return Promise.resolve(discovery);
     },
     install: args.install ?? (() => Promise.resolve()),
+    checkForUpdate:
+      args.checkForUpdate ?? (() => Promise.resolve({ upToDate: false })),
     update: args.update ?? (() => Promise.resolve()),
     status: args.status ?? (() => Promise.resolve({})),
     loginAndSwitch: args.loginAndSwitch ?? (() => Promise.resolve()),
@@ -879,6 +885,82 @@ describe("runClackWizard", () => {
     expect(calls).toEqual([]);
   });
 
+  it("skips the update question when the Braintrust CLI is already up to date", async () => {
+    const calls: string[] = [];
+    const { events } = createPrompts({
+      selects: ["yes", "manual", "confirm", "understood"],
+    });
+    const deps = buildDeps({
+      braintrustCli: createBraintrustCliStub({
+        discoveries: [
+          { installed: true, commandPath: "/bin/bt", version: "bt 0.10.0" },
+        ],
+        checkForUpdate: (commandPath) => {
+          calls.push(`check:${commandPath}`);
+          return Promise.resolve({ upToDate: true });
+        },
+        update: (commandPath) => {
+          calls.push(`update:${commandPath}`);
+          return Promise.resolve();
+        },
+        status: () => {
+          calls.push("status");
+          return Promise.resolve({});
+        },
+        loginAndSwitch: () => {
+          calls.push("login");
+          return Promise.resolve();
+        },
+      }),
+    });
+
+    await runClackWizard(deps);
+
+    expect(events).not.toContain(`select:${CLI_UPDATE_MESSAGE}`);
+    expect(events).not.toContain("spinner.start:Updating Braintrust CLI...");
+    expect(
+      events.some((event) => event.includes("Braintrust CLI is up to date")),
+    ).toBe(false);
+    expect(calls).toEqual(["check:/bin/bt", "status", "login"]);
+  });
+
+  it("updates when the update check fails and the user accepts", async () => {
+    const calls: string[] = [];
+    const { events } = createPrompts({
+      selects: ["no", "yes", "manual", "confirm", "understood"],
+    });
+    const deps = buildDeps({
+      braintrustCli: createBraintrustCliStub({
+        discoveries: [
+          { installed: true, commandPath: "/bin/bt", version: "bt 0.10.0" },
+        ],
+        checkForUpdate: () => Promise.reject(new Error("network down")),
+        update: (commandPath) => {
+          calls.push(`update:${commandPath}`);
+          return Promise.resolve();
+        },
+        status: () => {
+          calls.push("status");
+          return Promise.resolve({});
+        },
+        loginAndSwitch: () => {
+          calls.push("login");
+          return Promise.resolve();
+        },
+      }),
+    });
+
+    await runClackWizard(deps);
+
+    expect(
+      events.some((event) =>
+        event.includes("Could not check for Braintrust CLI updates"),
+      ),
+    ).toBe(false);
+    expect(events).toContain(`select:${CLI_UPDATE_MESSAGE}`);
+    expect(calls).toEqual(["update:/bin/bt", "status", "login"]);
+  });
+
   it("updates and configures an installed Braintrust CLI when accepted", async () => {
     const calls: string[] = [];
     const { events } = createPrompts({