diff --git a/packages/cli/src/commands/transcribe.test.ts b/packages/cli/src/commands/transcribe.test.ts
index ea43a07fbb..3bfd142c80 100644
--- a/packages/cli/src/commands/transcribe.test.ts
+++ b/packages/cli/src/commands/transcribe.test.ts
@@ -39,6 +39,7 @@ describe("transcribe command", () => {
       new WhisperUnavailableError("whisper-cpp not found. Install: brew install whisper-cpp"),
     );
     vi.spyOn(console, "log").mockImplementation(() => {});
+    vi.spyOn(console, "error").mockImplementation(() => {});
   });
 
   afterEach(() => {
@@ -65,6 +66,15 @@ describe("transcribe command", () => {
     expect(process.exitCode).toBe(0);
     expect(trackTranscribeUnavailable).toHaveBeenCalledWith({ optional: true });
     expect(trackCommandFailure).not.toHaveBeenCalled();
+
+    const diagnostic = vi.mocked(console.error).mock.calls.at(-1)?.[0];
+    expect(typeof diagnostic).toBe("string");
+    if (typeof diagnostic !== "string") throw new Error("Expected stderr diagnostic");
+    expect(JSON.parse(diagnostic)).toEqual({
+      level: "warning",
+      reason: "whisper_unavailable",
+      message: "whisper-cpp not found. Install: brew install whisper-cpp",
+    });
   });
 
   it("imports an SRT and exports an SRT sidecar from transcript.json", async () => {
diff --git a/packages/cli/src/commands/transcribe.ts b/packages/cli/src/commands/transcribe.ts
index 0c4ec4405f..adbfae1906 100644
--- a/packages/cli/src/commands/transcribe.ts
+++ b/packages/cli/src/commands/transcribe.ts
@@ -319,6 +319,18 @@ async function transcribeAudio(
     if (isWhisperUnavailable(err)) {
       trackTranscribeUnavailable({ optional: opts.optional === true });
       if (opts.json) {
+        // Keep the machine-readable result on stdout, but also surface the
+        // skipped prerequisite on stderr. Pipeline wrappers commonly discard
+        // successful stdout, so an optional exit 0 must not become silent.
+        if (opts.optional) {
+          console.error(
+            JSON.stringify({
+              level: "warning",
+              reason: "whisper_unavailable",
+              message,
+            }),
+          );
+        }
         console.log(JSON.stringify({ ok: false, skipped: true, reason: "whisper_unavailable" }));
       } else {
         spin?.stop(c.warn(`Captions skipped — ${message}`));
diff --git a/packages/cli/src/whisper/manager.test.ts b/packages/cli/src/whisper/manager.test.ts
index 763ccdc0e5..75f4f0ff42 100644
--- a/packages/cli/src/whisper/manager.test.ts
+++ b/packages/cli/src/whisper/manager.test.ts
@@ -1,5 +1,9 @@
 import { describe, it, expect } from "vitest";
-import { WhisperUnavailableError, isWhisperUnavailable } from "./manager.js";
+import {
+  WhisperUnavailableError,
+  getInstallInstructions,
+  isWhisperUnavailable,
+} from "./manager.js";
 
 describe("isWhisperUnavailable", () => {
   it("recognizes WhisperUnavailableError instances", () => {
@@ -28,3 +32,12 @@ describe("isWhisperUnavailable", () => {
     expect(isWhisperUnavailable(undefined)).toBe(false);
   });
 });
+
+describe("getInstallInstructions", () => {
+  it("points Windows users to the prebuilt x64 archive before the source-build fallback", () => {
+    const instructions = getInstallInstructions("win32");
+
+    expect(instructions).toContain("whisper-bin-x64.zip");
+    expect(instructions).toContain("cmake");
+  });
+});
diff --git a/packages/cli/src/whisper/manager.ts b/packages/cli/src/whisper/manager.ts
index 7985283382..8b821347e5 100644
--- a/packages/cli/src/whisper/manager.ts
+++ b/packages/cli/src/whisper/manager.ts
@@ -151,15 +151,15 @@ export function findWhisper(): WhisperResult | undefined {
   return findFromEnv() ?? findFromSystem() ?? findBuiltBinary();
 }
 
-export function getInstallInstructions(): string {
-  if (platform() === "darwin") {
+export function getInstallInstructions(targetPlatform: NodeJS.Platform = platform()): string {
+  if (targetPlatform === "darwin") {
     return "brew install whisper-cpp";
   }
-  if (platform() === "linux") {
+  if (targetPlatform === "linux") {
     return "Build from source: https://github.com/ggml-org/whisper.cpp#building (requires cmake and a C compiler)";
   }
-  if (platform() === "win32") {
-    return "Build with cmake: https://github.com/ggml-org/whisper.cpp#building";
+  if (targetPlatform === "win32") {
+    return "Download the prebuilt whisper-bin-x64.zip from https://github.com/ggml-org/whisper.cpp/releases/latest, or build with cmake: https://github.com/ggml-org/whisper.cpp#building";
   }
   return "See https://github.com/ggml-org/whisper.cpp#building";
 }