diff --git a/cli/src/__tests__/onboard-service.test.ts b/cli/src/__tests__/onboard-service.test.ts
index 5b3f406433..1b2b6baf4a 100644
--- a/cli/src/__tests__/onboard-service.test.ts
+++ b/cli/src/__tests__/onboard-service.test.ts
@@ -1,5 +1,5 @@
 import { describe, expect, it, vi } from "vitest";
-import { handleOnboardService, isInstallableReleaseVersion } from "../onboard-service.js";
+import { handleOnboardService, isInstallableReleaseVersion, shouldOfferForegroundStart } from "../onboard-service.js";
 
 function supportedDetection() {
   return {
@@ -138,3 +138,27 @@ describe("isInstallableReleaseVersion", () => {
     expect(isInstallableReleaseVersion("not-a-version")).toBe(false);
   });
 });
+
+describe("shouldOfferForegroundStart", () => {
+  const base = { serviceInstalled: false, startAlreadyDecided: false, invokedByRun: false, interactive: true };
+
+  it("offers a foreground start on a plain interactive onboard", () => {
+    expect(shouldOfferForegroundStart(base)).toBe(true);
+  });
+
+  it("never prompts after the service was installed and started", () => {
+    expect(shouldOfferForegroundStart({ ...base, serviceInstalled: true })).toBe(false);
+  });
+
+  it("never prompts when the start decision was already made by flags", () => {
+    expect(shouldOfferForegroundStart({ ...base, startAlreadyDecided: true })).toBe(false);
+  });
+
+  it("never prompts when run itself invoked onboarding", () => {
+    expect(shouldOfferForegroundStart({ ...base, invokedByRun: true })).toBe(false);
+  });
+
+  it("never prompts without an interactive terminal", () => {
+    expect(shouldOfferForegroundStart({ ...base, interactive: false })).toBe(false);
+  });
+});
diff --git a/cli/src/commands/onboard.ts b/cli/src/commands/onboard.ts
index 31850714d7..db94cb24a7 100644
--- a/cli/src/commands/onboard.ts
+++ b/cli/src/commands/onboard.ts
@@ -52,7 +52,7 @@ import {
   trackInstallStarted,
   trackInstallCompleted,
 } from "../telemetry.js";
-import { handleOnboardService } from "../onboard-service.js";
+import { handleOnboardService, shouldOfferForegroundStart } from "../onboard-service.js";
 import { readInstallManifest, isManagedExecutable } from "../install-store.js";
 
 type SetupMode = "quickstart" | "advanced";
@@ -459,7 +459,7 @@ export async function onboard(opts: OnboardOptions): Promise<void> {
     const serviceInstalled = await handleOnboardService(opts);
 
     let shouldRunNow = !serviceInstalled && (opts.run === true || opts.yes === true);
-    if (!shouldRunNow && !opts.invokedByRun && process.stdin.isTTY && process.stdout.isTTY) {
+    if (shouldOfferForegroundStart({ serviceInstalled, startAlreadyDecided: shouldRunNow, invokedByRun: opts.invokedByRun === true, interactive: Boolean(process.stdin.isTTY && process.stdout.isTTY) })) {
       const answer = await p.confirm({
         message: "Start Paperclip now?",
         initialValue: true,
@@ -725,7 +725,7 @@ export async function onboard(opts: OnboardOptions): Promise<void> {
   const serviceInstalled = await handleOnboardService(opts);
 
   let shouldRunNow = !serviceInstalled && (opts.run === true || opts.yes === true);
-  if (!shouldRunNow && !opts.invokedByRun && process.stdin.isTTY && process.stdout.isTTY) {
+  if (shouldOfferForegroundStart({ serviceInstalled, startAlreadyDecided: shouldRunNow, invokedByRun: opts.invokedByRun === true, interactive: Boolean(process.stdin.isTTY && process.stdout.isTTY) })) {
     const answer = await p.confirm({
       message: "Start Paperclip now?",
       initialValue: true,
diff --git a/cli/src/onboard-service.ts b/cli/src/onboard-service.ts
index 268f121e51..1f52e970aa 100644
--- a/cli/src/onboard-service.ts
+++ b/cli/src/onboard-service.ts
@@ -165,3 +165,20 @@ export async function handleOnboardService(
   deps.success(`Installed and started ${detection.manager.serviceName}.`);
   return true;
 }
+
+// Onboarding falls back to offering a foreground start when nothing else
+// will serve. A just-installed service is already serving, so offering the
+// start would only run the user into the already-running instance guard.
+export function shouldOfferForegroundStart(options: {
+  serviceInstalled: boolean;
+  startAlreadyDecided: boolean;
+  invokedByRun: boolean;
+  interactive: boolean;
+}): boolean {
+  return (
+    !options.startAlreadyDecided &&
+    !options.serviceInstalled &&
+    !options.invokedByRun &&
+    options.interactive
+  );
+}