diff --git a/setup/channels/run-channel-skill.ts b/setup/channels/run-channel-skill.ts
index b1248affc..0d1d6aea1 100644
--- a/setup/channels/run-channel-skill.ts
+++ b/setup/channels/run-channel-skill.ts
@@ -106,6 +106,10 @@ export async function runChannelSkill(
     skipEffects: overrides.skipEffects,
     reporter: overrides.reporter, // undefined ⇒ runSkill's TTY-gated spinner
     reuse: overrides.reuse ?? true, // offer to reuse credentials already in .env
+    // Handoff context for the `?` help-escape: a lone `?` at any of this skill's
+    // prompts hands the operator off to interactive Claude scoped to this channel.
+    channel: overrides.channel ?? channel,
+    step: overrides.step ?? `${channel}-install`,
   });
   if (!fullyApplied(res)) {
     if (res.deferred.length) p.log.warn(`Still needs: ${res.deferred.join(', ')}`);
diff --git a/setup/lib/skill-driver.test.ts b/setup/lib/skill-driver.test.ts
index b7db604ff..4ac725a0a 100644
--- a/setup/lib/skill-driver.test.ts
+++ b/setup/lib/skill-driver.test.ts
@@ -1,4 +1,4 @@
-import { describe, it, expect } from 'vitest';
+import { describe, it, expect, vi } from 'vitest';
 import { mkdtempSync, mkdirSync, writeFileSync, chmodSync } from 'node:fs';
 import { tmpdir } from 'node:os';
 import { join } from 'node:path';
@@ -6,6 +6,35 @@ import { join } from 'node:path';
 import { runSkill, hostExec, hostExecStream, promptValidator, clackPrompter, type RunSkillOptions } from './skill-driver.js';
 import { fullyApplied, type Prompter, type StepReporter } from '../../scripts/skill-apply.js';
 
+// Shared test state for the clack + claude-handoff mocks (hoisted so the vi.mock
+// factories — which run before imports — can close over it). `answers` is the
+// queue each mocked text/password prompt pops from; `handoffSpy` stands in for
+// the interactive Claude handoff; `lastValidate` captures the validate callback
+// the prompter handed clack so we can prove the `?` help-escape is wired in.
+const ce = vi.hoisted(() => ({
+  handoffSpy: vi.fn(async (_ctx: { channel: string; step: string; stepDescription: string }) => true),
+  answers: [] as string[],
+  lastValidate: { fn: undefined as undefined | ((v: string) => string | Error | void | undefined) },
+}));
+
+// Keep isHelpEscape + validateWithHelpEscape real (clackPrompter uses them); only
+// the interactive handoff is replaced with a spy so the test never spawns Claude.
+vi.mock('./claude-handoff.js', async (importActual) => {
+  const actual = await importActual<typeof import('./claude-handoff.js')>();
+  return { ...actual, offerClaudeHandoff: ce.handoffSpy };
+});
+
+// Drive clackPrompter's prompts from the `answers` queue and record the validate
+// callback it passes through, instead of opening a real TTY prompt.
+vi.mock('@clack/prompts', async (importActual) => {
+  const actual = await importActual<typeof import('@clack/prompts')>();
+  const fromQueue = async (o: { validate?: (v: string) => string | Error | void | undefined }): Promise<string> => {
+    ce.lastValidate.fn = o?.validate;
+    return ce.answers.shift() ?? '';
+  };
+  return { ...actual, text: vi.fn(fromQueue), password: vi.fn(fromQueue) };
+});
+
 // A small SKILL.md exercising the three things the driver wires: an operator
 // block (relayed via tell), a secret prompt (asked via ask), and a wire run
 // (executed via exec) consuming the captured input.
@@ -193,6 +222,42 @@ describe('thin skill driver', () => {
     expect(typeof clackPrompter().open).toBe('function');
   });
 
+  it('clackPrompter intercepts a lone "?" → hands off to Claude with context, then re-asks', async () => {
+    const prevTTY = process.stdout.isTTY;
+    process.stdout.isTTY = true; // the `?` help-escape only fires at a real terminal
+    try {
+      ce.handoffSpy.mockClear();
+      ce.answers = ['?', 'real-token']; // first answer is the help-escape, second is the real value
+      const ans = await clackPrompter({ channel: 'telegram', step: 'paste-token' }).ask(
+        'token',
+        'Paste your token.',
+        false,
+        '^[0-9a-zA-Z-]+$',
+      );
+      expect(ans).toBe('real-token'); // re-asked after the handoff, returns the second answer
+      expect(ce.handoffSpy).toHaveBeenCalledTimes(1);
+      expect(ce.handoffSpy.mock.calls[0][0]).toEqual({
+        channel: 'telegram',
+        step: 'paste-token',
+        stepDescription: 'Paste your token.',
+      });
+      // The validate handed to clack lets `?` through (so the escape reaches us)
+      // but still rejects a value that fails the prompt's own regex.
+      expect(ce.lastValidate.fn?.('?')).toBeUndefined();
+      expect(ce.lastValidate.fn?.('has space')).toBeTruthy();
+    } finally {
+      process.stdout.isTTY = prevTTY;
+    }
+  });
+
+  it('clackPrompter passes a normal answer straight through — no handoff', async () => {
+    ce.handoffSpy.mockClear();
+    ce.answers = ['just-a-token'];
+    const ans = await clackPrompter({ channel: 'telegram', step: 'paste-token' }).ask('token', 'Paste your token.', false);
+    expect(ans).toBe('just-a-token');
+    expect(ce.handoffSpy).not.toHaveBeenCalled();
+  });
+
   it('promptValidator honors flags:i (case-insensitive) and min (rejects short); error overrides the message', () => {
     const ci = promptValidator('^https://', { flags: 'i' });
     expect(ci).toBeDefined();
diff --git a/setup/lib/skill-driver.ts b/setup/lib/skill-driver.ts
index 99c065597..6b513c7d0 100644
--- a/setup/lib/skill-driver.ts
+++ b/setup/lib/skill-driver.ts
@@ -17,6 +17,7 @@ import { applySkill, fullyApplied, type ApplyResult, type Prompter, type PromptO
 import { parseDirectives, promptVar } from '../../scripts/skill-directives.js';
 import { isHeadless } from '../platform.js';
 import { openUrl } from './browser.js';
+import { isHelpEscape, offerClaudeHandoff, validateWithHelpEscape } from './claude-handoff.js';
 import { startSpinner } from './runner.js';
 
 /**
@@ -48,19 +49,59 @@ export function promptValidator(
   };
 }
 
-export function clackPrompter(): Prompter {
+/**
+ * Handoff context for the `?` help-escape (Step 8 / mechanism M3). A lone `?` at
+ * any prompt hands the operator to interactive Claude with this context, then
+ * re-asks the same prompt. Both fields are optional so a bare `clackPrompter()`
+ * (e.g. the standalone CLI below) still works — it just hands off with a generic
+ * `setup` channel and the prompt's own var name as the step.
+ */
+export interface PrompterContext {
+  /** Channel this run is wiring (e.g. 'telegram') — surfaced to the handoff. */
+  channel?: string;
+  /** Short label for the current setup step — surfaced to the handoff. */
+  step?: string;
+}
+
+export function clackPrompter(ctx: PrompterContext = {}): Prompter {
+  // The `?` help-escape is only meaningful at a real terminal: it hands the
+  // operator off to an interactive Claude session (stdio inherited). In a
+  // headless / non-TTY run nobody can type `?` into a clack prompt anyway, and
+  // we must never spawn an interactive child without a TTY — so it's a no-op
+  // there (read at ask-time so a re-run picks up a terminal that appears later).
+  async function ask(
+    varName: string,
+    question: string,
+    secret: boolean,
+    validate?: string,
+    opts?: PromptOpts,
+  ): Promise<string | undefined> {
+    const check = promptValidator(validate, opts);
+    // Wrap the validator so a lone `?` short-circuits format checks and comes
+    // back as a literal "?" instead of being rejected — we intercept it below.
+    const guarded = validateWithHelpEscape(check);
+    // clearOnError wipes a rejected secret so the operator re-pastes cleanly
+    // (a half-pasted token isn't left masked in the field).
+    const ans = secret
+      ? await p.password({ message: question, validate: guarded, clearOnError: true })
+      : await p.text({ message: question, validate: guarded });
+    if (p.isCancel(ans)) return undefined; // cancelled ⇒ defer
+    if (isHelpEscape(ans) && process.stdout.isTTY) {
+      // Operator asked for help: hand off to interactive Claude with this
+      // prompt's context, then re-ask the same prompt. Recursion is operator-
+      // bounded — they decide when to stop typing `?`.
+      await offerClaudeHandoff({
+        channel: ctx.channel ?? 'setup',
+        step: ctx.step ?? varName,
+        stepDescription: question,
+      });
+      return ask(varName, question, secret, validate, opts);
+    }
+    const v = String(ans).trim();
+    return v.length ? v : undefined;
+  }
   return {
-    async ask(_varName, question, secret, validate, opts) {
-      const check = promptValidator(validate, opts);
-      // clearOnError wipes a rejected secret so the operator re-pastes cleanly
-      // (a half-pasted token isn't left masked in the field).
-      const ans = secret
-        ? await p.password({ message: question, validate: check, clearOnError: true })
-        : await p.text({ message: question, validate: check });
-      if (p.isCancel(ans)) return undefined; // cancelled ⇒ defer
-      const v = String(ans).trim();
-      return v.length ? v : undefined;
-    },
+    ask,
     tell(text) {
       p.note(text, 'Do this');
     },
@@ -263,6 +304,14 @@ export interface RunSkillOptions {
    * (`spinnerReporter`); pass a fake in tests or a no-op to silence.
    */
   reporter?: StepReporter;
+  /**
+   * Handoff context for the `?` help-escape (Step 8 / mechanism M3), threaded
+   * into the default `clackPrompter`. A lone `?` at any prompt hands the operator
+   * off to interactive Claude with this `channel` + `step` label, then re-asks.
+   * Ignored when an explicit `prompter` is injected (the injector owns its I/O).
+   */
+  channel?: string;
+  step?: string;
 }
 
 /**
@@ -272,7 +321,7 @@ export interface RunSkillOptions {
  */
 export async function runSkill(skillDir: string, opts: RunSkillOptions = {}): Promise<ApplyResult> {
   const projectRoot = opts.projectRoot ?? process.cwd();
-  const prompter = opts.prompter ?? clackPrompter();
+  const prompter = opts.prompter ?? clackPrompter({ channel: opts.channel, step: opts.step });
   let inputs = opts.inputs;
   // Offer to reuse credentials already in .env before the engine prompts for them.
   if (opts.reuse && prompter.confirm) {