diff --git a/packages/cli/src/commands/transcribe.ts b/packages/cli/src/commands/transcribe.ts
index 4605ffdd39..7a283b736e 100644
--- a/packages/cli/src/commands/transcribe.ts
+++ b/packages/cli/src/commands/transcribe.ts
@@ -14,6 +14,7 @@ import { resolve, join, extname, dirname } from "node:path";
 import * as clack from "@clack/prompts";
 import { c } from "../ui/colors.js";
 import { DEFAULT_MODEL } from "../whisper/manager.js";
+import { trackCommandFailure } from "../telemetry/events.js";
 
 export default defineCommand({
   meta: {
@@ -52,7 +53,9 @@ export default defineCommand({
   async run({ args }) {
     const inputPath = resolve(args.input);
     if (!existsSync(inputPath)) {
-      console.error(c.error(`File not found: ${args.input}`));
+      const message = `File not found: ${args.input}`;
+      trackCommandFailure("transcribe", message);
+      console.error(c.error(message));
       process.exit(1);
     }
 
@@ -87,7 +90,9 @@ async function importTranscript(inputPath: string, dir: string, json: boolean):
   const { words, format } = loadTranscript(inputPath);
 
   if (words.length === 0) {
-    console.error(c.error("No words found in transcript."));
+    const message = "No words found in transcript.";
+    trackCommandFailure("transcribe", message);
+    console.error(c.error(message));
     process.exit(1);
   }
 
@@ -170,6 +175,7 @@ async function transcribeAudio(
     }
   } catch (err) {
     const message = err instanceof Error ? err.message : String(err);
+    trackCommandFailure("transcribe", err);
     if (opts.json) {
       console.log(JSON.stringify({ ok: false, error: message }));
     } else {
diff --git a/packages/cli/src/telemetry/events.test.ts b/packages/cli/src/telemetry/events.test.ts
index 761b4ef674..924c2ebe06 100644
--- a/packages/cli/src/telemetry/events.test.ts
+++ b/packages/cli/src/telemetry/events.test.ts
@@ -5,7 +5,8 @@ vi.mock("./client.js", () => ({
   trackEvent: (...args: unknown[]) => trackEvent(...args),
 }));
 
-const { trackRenderError, trackRenderObservation } = await import("./events.js");
+const { trackRenderError, trackRenderObservation, trackCommandFailure } =
+  await import("./events.js");
 
 describe("render telemetry events", () => {
   beforeEach(() => {
@@ -50,3 +51,38 @@ describe("render telemetry events", () => {
     );
   });
 });
+
+describe("trackCommandFailure", () => {
+  beforeEach(() => {
+    trackEvent.mockClear();
+  });
+
+  it("reports an Error as a command_error with name/message/stack", () => {
+    const err = new Error("ffmpeg is required to extract audio");
+    trackCommandFailure("transcribe", err);
+
+    expect(trackEvent).toHaveBeenCalledWith(
+      "cli_error",
+      expect.objectContaining({
+        kind: "command_error",
+        command: "transcribe",
+        error_name: "Error",
+        error_message: "ffmpeg is required to extract audio",
+        stack_trace: err.stack,
+      }),
+    );
+  });
+
+  it("coerces a non-Error reason (e.g. a string) into the message", () => {
+    trackCommandFailure("transcribe", "No words found in transcript.");
+
+    expect(trackEvent).toHaveBeenCalledWith(
+      "cli_error",
+      expect.objectContaining({
+        kind: "command_error",
+        command: "transcribe",
+        error_message: "No words found in transcript.",
+      }),
+    );
+  });
+});
diff --git a/packages/cli/src/telemetry/events.ts b/packages/cli/src/telemetry/events.ts
index 508b72f4f8..767f376374 100644
--- a/packages/cli/src/telemetry/events.ts
+++ b/packages/cli/src/telemetry/events.ts
@@ -284,6 +284,21 @@ export function trackCliError(props: {
   });
 }
 
+// Report why a command failed before it exits non-zero. cli_command_result
+// records the failure but not the reason; this fills that gap via cli_error so
+// command failures are diagnosable. Enqueues synchronously — the process `exit`
+// handler flushes it. Drop this into any command's failure path.
+export function trackCommandFailure(command: string, err: unknown): void {
+  const error = err instanceof Error ? err : new Error(String(err));
+  trackCliError({
+    error_name: error.name,
+    error_message: error.message,
+    stack_trace: error.stack,
+    command,
+    kind: "command_error",
+  });
+}
+
 export function trackRenderFeedback(props: {
   rating: number;
   renderDurationMs: number;