diff --git a/packages/web/src/auth/posthog/track.ts b/packages/web/src/auth/posthog/track.ts
index 523bd5c4c..c79524a56 100644
--- a/packages/web/src/auth/posthog/track.ts
+++ b/packages/web/src/auth/posthog/track.ts
@@ -13,7 +13,7 @@ export type ProductEvent =
   | "shortcut_showcase_step_redone"
   | "shortcut_showcase_skipped"
   | "shortcut_showcase_finished"
-  | "shortcut_showcase_assist_shown"
+  | "shortcut_showcase_assist_used"
   | "checklist_shown"
   | "checklist_item_completed"
   | "checklist_dismissed"
diff --git a/packages/web/src/components/OnboardingChecklist/OnboardingChecklist.tsx b/packages/web/src/components/OnboardingChecklist/OnboardingChecklist.tsx
index 4729479d3..2689324f0 100644
--- a/packages/web/src/components/OnboardingChecklist/OnboardingChecklist.tsx
+++ b/packages/web/src/components/OnboardingChecklist/OnboardingChecklist.tsx
@@ -62,7 +62,7 @@ const ChecklistCard: FC = () => {
           <>
             <div className="mb-2 flex items-center justify-between">
               <span className="font-semibold text-sm">
-                Practice on real events
+                Practice on sample events
               </span>
               <span className="text-text-muted text-xs">
                 {doneCount}/{CHECKLIST_ITEMS.length}
@@ -71,9 +71,29 @@ const ChecklistCard: FC = () => {
             <ul className="flex flex-col gap-1.5">
               {CHECKLIST_ITEMS.map((item) => {
                 const isComplete = Boolean(completed[item.id]);
+
+                // The exit of the flow, so it reads as a real CTA rather
+                // than one more thing to check off.
+                if (item.id === "signUp" && !isComplete) {
+                  return (
+                    <li key={item.id} className="mt-1">
+                      <button
+                        type="button"
+                        className="c-focus-ring inline-flex w-full items-center justify-center rounded-3xl bg-accent px-4 py-1.5 font-medium text-on-accent text-xs transition-all hover:brightness-110"
+                        onClick={() => {
+                          track("signup_started", { source: "checklist" });
+                          openModal("signUp");
+                        }}
+                      >
+                        {item.label}
+                      </button>
+                    </li>
+                  );
+                }
+
                 const keycaps = "keycaps" in item ? item.keycaps : undefined;
-                const row = (
-                  <>
+                return (
+                  <li key={item.id} className="flex items-center gap-2">
                     {isComplete ? (
                       <CheckCircleIcon
                         className="shrink-0 text-accent"
@@ -98,24 +118,6 @@ const ChecklistCard: FC = () => {
                     {keycaps && !isComplete && (
                       <ShortcutKeys className="ml-auto" keys={[...keycaps]} />
                     )}
-                  </>
-                );
-                return (
-                  <li key={item.id} className="flex items-center gap-2">
-                    {item.id === "signUp" && !isComplete ? (
-                      <button
-                        type="button"
-                        className="c-focus-ring flex w-full items-center gap-2 rounded-md text-left hover:bg-surface-overlay"
-                        onClick={() => {
-                          track("signup_started", { source: "checklist" });
-                          openModal("signUp");
-                        }}
-                      >
-                        {row}
-                      </button>
-                    ) : (
-                      row
-                    )}
                   </li>
                 );
               })}
diff --git a/packages/web/src/components/OnboardingChecklist/checklist.items.ts b/packages/web/src/components/OnboardingChecklist/checklist.items.ts
index 32173f2cc..98d64a24a 100644
--- a/packages/web/src/components/OnboardingChecklist/checklist.items.ts
+++ b/packages/web/src/components/OnboardingChecklist/checklist.items.ts
@@ -24,7 +24,7 @@ export const CHECKLIST_ITEMS = [
   },
   {
     id: "placeDraft",
-    label: "Drop a new event on the grid",
+    label: "Place a new event on the grid",
     keycaps: KEYMAP.moveEvent.keycaps,
   },
   { id: "undo", label: "Undo a change", keycaps: KEYMAP.undo.keycaps },
diff --git a/packages/web/src/components/ShortcutShowcase/ShortcutShowcase.test.tsx b/packages/web/src/components/ShortcutShowcase/ShortcutShowcase.test.tsx
index e13d82dbc..f55e5f838 100644
--- a/packages/web/src/components/ShortcutShowcase/ShortcutShowcase.test.tsx
+++ b/packages/web/src/components/ShortcutShowcase/ShortcutShowcase.test.tsx
@@ -3,7 +3,10 @@ import userEvent from "@testing-library/user-event";
 import { STORAGE_KEYS } from "@web/common/constants/storage.constants";
 import { persistentBrowserStore } from "@web/common/storage/browser-key-value.store";
 import { ShortcutShowcase } from "@web/components/ShortcutShowcase/ShortcutShowcase";
-import { SHOWCASE_STEP_IDS } from "@web/components/ShortcutShowcase/showcase.steps";
+import {
+  SHOWCASE_STEP_IDS,
+  type ShowcaseStepId,
+} from "@web/components/ShortcutShowcase/showcase.steps";
 import {
   initialShortcutShowcaseState,
   shortcutShowcaseActions,
@@ -23,6 +26,16 @@ const pressKey = (key: string, init: KeyboardEventInit = {}) => {
 const currentStepId = () =>
   SHOWCASE_STEP_IDS[useShortcutShowcaseStore.getState().stepIndex];
 
+/** Jumps straight to a lesson; there is no store action for an arbitrary step. */
+const showStep = (id: ShowcaseStepId) => {
+  act(() =>
+    useShortcutShowcaseStore.setState({
+      isActive: true,
+      stepIndex: SHOWCASE_STEP_IDS.indexOf(id),
+    }),
+  );
+};
+
 describe("ShortcutShowcase", () => {
   beforeEach(() => {
     useShortcutShowcaseStore.setState(initialShortcutShowcaseState);
@@ -116,6 +129,47 @@ describe("ShortcutShowcase", () => {
     ).toBe("true");
   });
 
+  it("offers 'Do it for me' from the first step, and swaps it out at graduation", async () => {
+    const user = userEvent.setup();
+    render(<ShortcutShowcase />);
+    act(() => shortcutShowcaseActions.start());
+
+    // No idle wait or failed attempt required: the way out is always offered.
+    await user.click(screen.getByRole("button", { name: "Do it for me" }));
+    expect(currentStepId()).toBe("save");
+
+    showStep("graduation");
+    expect(screen.queryByRole("button", { name: "Do it for me" })).toBeNull();
+    expect(screen.getByRole("button", { name: "Enter Compass" })).toBeTruthy();
+  });
+
+  it("shows the stretch hint one phase at a time: Tab, then Shift+Arrow", async () => {
+    const user = userEvent.setup();
+    render(<ShortcutShowcase />);
+    showStep("resizeEdge");
+
+    // Phase one: only the key that moves focus onto the end time.
+    expect(screen.getByTestId("tab-icon")).toBeTruthy();
+    expect(screen.queryByTestId("shift-icon")).toBeNull();
+    expect(screen.queryByTestId("arrowdown-icon")).toBeNull();
+
+    pressKey("Tab");
+
+    // Phase two: the end edge has focus, so the chord replaces Tab.
+    expect(screen.queryByTestId("tab-icon")).toBeNull();
+    expect(screen.getByTestId("shift-icon")).toBeTruthy();
+    expect(screen.getByTestId("arrowdown-icon")).toBeTruthy();
+
+    // Leaving and returning re-seeds the start edge, so the lesson restarts
+    // at phase one rather than stranding the user on the chord.
+    pressKey("ArrowDown", { shiftKey: true });
+    expect(currentStepId()).toBe("placeDraft");
+    await user.click(screen.getByRole("button", { name: "Previous" }));
+    expect(currentStepId()).toBe("resizeEdge");
+    expect(screen.getByTestId("tab-icon")).toBeTruthy();
+    expect(screen.queryByTestId("shift-icon")).toBeNull();
+  });
+
   it("Escape confirms once, lesson keys fall through, second Escape skips", () => {
     render(<ShortcutShowcase />);
     act(() => shortcutShowcaseActions.start());
diff --git a/packages/web/src/components/ShortcutShowcase/ShortcutShowcase.tsx b/packages/web/src/components/ShortcutShowcase/ShortcutShowcase.tsx
index a542de6cd..0186796a0 100644
--- a/packages/web/src/components/ShortcutShowcase/ShortcutShowcase.tsx
+++ b/packages/web/src/components/ShortcutShowcase/ShortcutShowcase.tsx
@@ -8,7 +8,6 @@ import {
 } from "react";
 import { track } from "@web/auth/posthog/track";
 import { Z_INDEX_MODAL } from "@web/common/constants/web.constants";
-import { isEditableKeyboardTarget } from "@web/common/utils/form/form.util";
 import { PracticeCalendar } from "@web/components/ShortcutShowcase/PracticeCalendar";
 import {
   clearFocus,
@@ -34,7 +33,7 @@ import {
 import {
   getShowcaseStep,
   SHOWCASE_STEP_IDS,
-  type ShowcaseStepId,
+  STRETCH_KEYCAPS,
 } from "@web/components/ShortcutShowcase/showcase.steps";
 import {
   selectShowcaseActive,
@@ -55,9 +54,6 @@ const TEXT_BUTTON_CLASS =
 const PRIMARY_BUTTON_CLASS =
   "c-button c-button-primary rounded-full px-4 py-1.5 text-xs";
 
-const ASSIST_IDLE_MS = 15_000;
-const ASSIST_ATTEMPT_THRESHOLD = 2;
-
 const ARROW_DIRECTIONS: Record<string, PracticeDirection> = {
   ArrowUp: "up",
   ArrowDown: "down",
@@ -65,43 +61,6 @@ const ARROW_DIRECTIONS: Record<string, PracticeDirection> = {
   ArrowRight: "right",
 };
 
-/** "Show me" fallback, ported from the retired tour's assist hook. */
-function useShowcaseAssist(stepId: ShowcaseStepId): boolean {
-  const [isVisible, setIsVisible] = useState(false);
-  const attemptsRef = useRef(0);
-  const revealedRef = useRef(false);
-
-  useEffect(() => {
-    setIsVisible(false);
-    attemptsRef.current = 0;
-    revealedRef.current = false;
-    if (stepId === "graduation") return;
-
-    const reveal = () => {
-      if (revealedRef.current) return;
-      revealedRef.current = true;
-      setIsVisible(true);
-      track("shortcut_showcase_assist_shown", { step: stepId });
-    };
-
-    const idleTimer = window.setTimeout(reveal, ASSIST_IDLE_MS);
-    const onKeyDown = (event: KeyboardEvent) => {
-      // Typing a title is progress, not a failed attempt at the shortcut.
-      if (isEditableKeyboardTarget(event)) return;
-      attemptsRef.current += 1;
-      if (attemptsRef.current >= ASSIST_ATTEMPT_THRESHOLD) reveal();
-    };
-
-    document.addEventListener("keydown", onKeyDown);
-    return () => {
-      window.clearTimeout(idleTimer);
-      document.removeEventListener("keydown", onKeyDown);
-    };
-  }, [stepId]);
-
-  return isVisible;
-}
-
 /**
  * Full-screen practice arena shown before a new user ever sees the real
  * calendar. Bindings come from KEYMAP (shared with the real handlers);
@@ -115,7 +74,6 @@ const ShowcaseTakeover: FC = () => {
   );
   const stepId = stepIdAt(stepIndex);
   const step = getShowcaseStep(stepId);
-  const isAssistVisible = useShowcaseAssist(stepId);
 
   // The takeover owns the keyboard: silence every real app handler
   // (useAppShortcut, the e-sequence, bare-letter s/h) while it is up.
@@ -390,7 +348,9 @@ const ShowcaseTakeover: FC = () => {
     return () => document.removeEventListener("keydown", onKeyDown, true);
   }, [apply]);
 
-  const showMe = () => {
+  // Performs the lesson's action on the practice board, then moves on.
+  const doItForMe = () => {
+    track("shortcut_showcase_assist_used", { step: stepId });
     switch (stepId) {
       case "create":
         apply(createDraft);
@@ -434,14 +394,15 @@ const ShowcaseTakeover: FC = () => {
       case "hardcore":
         apply((state) => (state.hardcoreOn ? state : toggleHardcore(state)));
         break;
-      case "graduation":
-        shortcutShowcaseActions.finish();
-        return;
     }
     advance();
   };
 
   const progressPercent = ((stepIndex + 1) / SHOWCASE_STEP_IDS.length) * 100;
+  // The stretch lesson teaches Tab first, then the chord, so it hints one
+  // press at a time rather than showing all three keys at once.
+  const isStretchPhase = stepId === "resizeEdge" && practice.edge === "end";
+  const keycaps = isStretchPhase ? STRETCH_KEYCAPS : step.keycaps;
 
   return (
     <section
@@ -493,7 +454,7 @@ const ShowcaseTakeover: FC = () => {
               </div>
               <h2 className="font-semibold text-lg text-text">{step.title}</h2>
               <p className="text-sm text-text-muted">{step.body}</p>
-              {step.keycaps && <ShortcutKeys keys={[...step.keycaps]} />}
+              {keycaps && <ShortcutKeys keys={[...keycaps]} />}
               <div className="flex items-center gap-2 pt-2">
                 {stepId === "graduation" ? (
                   <button
@@ -504,15 +465,13 @@ const ShowcaseTakeover: FC = () => {
                     Enter Compass
                   </button>
                 ) : (
-                  isAssistVisible && (
-                    <button
-                      type="button"
-                      className={PRIMARY_BUTTON_CLASS}
-                      onClick={showMe}
-                    >
-                      Show me
-                    </button>
-                  )
+                  <button
+                    type="button"
+                    className={PRIMARY_BUTTON_CLASS}
+                    onClick={doItForMe}
+                  >
+                    Do it for me
+                  </button>
                 )}
                 {stepIndex > 0 && stepId !== "graduation" && (
                   <button
diff --git a/packages/web/src/components/ShortcutShowcase/showcase.steps.ts b/packages/web/src/components/ShortcutShowcase/showcase.steps.ts
index 71234224f..31c7d7ce8 100644
--- a/packages/web/src/components/ShortcutShowcase/showcase.steps.ts
+++ b/packages/web/src/components/ShortcutShowcase/showcase.steps.ts
@@ -1,5 +1,9 @@
+import { detectPlatform } from "@tanstack/react-hotkeys";
 import { KEYMAP } from "@web/shortcuts/keymap";
 
+// Prose has no keycap chips to expand "Mod" into, so spell the real key out.
+const MOD_KEY = detectPlatform() === "mac" ? "Cmd" : "Ctrl";
+
 /**
  * Single source of truth for showcase step order. Every shortcut concept the
  * app teaches lives here; the checklist in the real app only re-practices
@@ -31,10 +35,17 @@ export type ShowcaseStep = {
   keycaps?: readonly string[];
 };
 
+/**
+ * Second half of the resizeEdge lesson, swapped in once the end edge has
+ * focus so the row never reads as one three-key press. Stretching reuses the
+ * Shift+Arrow family bound by KEYMAP.moveEvent; the arrow stays literal
+ * because it demonstrates one direction, and only up/down stretch.
+ */
+export const STRETCH_KEYCAPS: readonly string[] = ["Shift", "ArrowDown"];
+
 /**
  * Keycaps reference KEYMAP so a remap updates the hints automatically;
- * keymap.test.ts pins the 1:1 cases. Direction-specific arrows in combined
- * hints stay literal because they demonstrate one direction of a family.
+ * keymap.test.ts pins the 1:1 cases.
  */
 const STEP_CONTENT: Record<ShowcaseStepId, Omit<ShowcaseStep, "id">> = {
   create: {
@@ -68,18 +79,20 @@ const STEP_CONTENT: Record<ShowcaseStepId, Omit<ShowcaseStep, "id">> = {
     keycaps: KEYMAP.moveEvent.keycaps,
   },
   resizeEdge: {
+    // Two phases: the hint swaps to Shift+Arrow once the end edge has focus,
+    // so the keycaps here only cover the first press.
     title: "Stretch the end time",
-    body: "Press Tab to focus the event's end time, then hold Shift and press an arrow to stretch it. The start stays put.",
-    keycaps: [...KEYMAP.edgeFocus.keycaps, "Shift", "ArrowDown"],
+    body: "Press Tab to focus the event's end time, then hold Shift and press the up or down arrow to stretch it. The start stays put.",
+    keycaps: KEYMAP.edgeFocus.keycaps,
   },
   placeDraft: {
     title: "Place a block anywhere",
-    body: "With nothing focused, hold Shift and press an arrow key to drop a new block right on the grid.",
+    body: "With nothing focused, hold Shift and press an arrow key to place a new block right on the grid.",
     keycaps: KEYMAP.moveEvent.keycaps,
   },
   undoRedo: {
     title: "Never stress a mistake",
-    body: "Press Mod+Z to undo your last change, then Mod+Shift+Z to bring it back.",
+    body: `Press ${MOD_KEY}+Z to undo your last change, then ${MOD_KEY}+Shift+Z to bring it back.`,
     keycaps: KEYMAP.undo.keycaps,
   },
   hardcore: {
diff --git a/packages/web/src/shortcuts/keymap.test.ts b/packages/web/src/shortcuts/keymap.test.ts
index 5f3f13847..8a3ea989a 100644
--- a/packages/web/src/shortcuts/keymap.test.ts
+++ b/packages/web/src/shortcuts/keymap.test.ts
@@ -77,6 +77,9 @@ describe("keymap ↔ showcase hint parity", () => {
     expect(getShowcaseStep("editTitle").keycaps).toBe(KEYMAP.editTitle.keycaps);
     expect(getShowcaseStep("eventJump").keycaps).toBe(KEYMAP.eventJump.keycaps);
     expect(getShowcaseStep("moveEvent").keycaps).toBe(KEYMAP.moveEvent.keycaps);
+    expect(getShowcaseStep("resizeEdge").keycaps).toBe(
+      KEYMAP.edgeFocus.keycaps,
+    );
     expect(getShowcaseStep("placeDraft").keycaps).toBe(
       KEYMAP.moveEvent.keycaps,
     );