diff --git a/apps/web/src/speech/useDictationShortcut.browser.test.tsx b/apps/web/src/speech/useDictationShortcut.browser.test.tsx
index 5bbc17b1ecc3d..8530391cd7f60 100644
--- a/apps/web/src/speech/useDictationShortcut.browser.test.tsx
+++ b/apps/web/src/speech/useDictationShortcut.browser.test.tsx
@@ -4,7 +4,8 @@ import { expect, it, vi } from "vite-plus/test";
 import { render } from "../../test/render";
 import { useDictationShortcut, type DictationKeyHandlers } from "./useDictationShortcut";
 
-vi.mock("../hooks/useSettings", () => ({ useClientSettings: () => "hold" }));
+const settings = vi.hoisted(() => ({ mode: "hold" as "hold" | "auto" | "toggle" }));
+vi.mock("../hooks/useSettings", () => ({ useClientSettings: () => settings.mode }));
 
 type ShortcutInput = Parameters<typeof useDictationShortcut>[0];
 
@@ -42,7 +43,8 @@ const press = (repeat = false) =>
     }),
   );
 
-function actions(available: boolean) {
+function actions(available: boolean, mode: typeof settings.mode = "hold") {
+  settings.mode = mode;
   return {
     available,
     state: { phase: "idle" as const, error: null, errorAction: null },
@@ -94,6 +96,28 @@ it("finishes a released hold after startup even if the chord was pressed again w
   expect(speech.stop).toHaveBeenCalledOnce();
 });
 
+it.each([
+  { mode: "hold", heldMs: 0, stops: 1 },
+  { mode: "auto", heldMs: 300, stops: 1 },
+  { mode: "auto", heldMs: 299, stops: 0 },
+] as const)(
+  "ends a $mode press held $heldMs ms when a chord modifier is released without the letter keyup",
+  async ({ mode, heldMs, stops }) => {
+    const speech = actions(true, mode);
+    using _platform = vi.spyOn(navigator, "platform", "get").mockReturnValue("MacIntel");
+    await using _screen = await render(<Probe speech={speech} />);
+    using clock = vi.spyOn(performance, "now").mockReturnValue(0);
+    press();
+    clock.mockReturnValue(heldMs);
+    window.dispatchEvent(new KeyboardEvent("keyup", { key: "Alt", code: "AltLeft" }));
+    await speech.start.mock.results[0]?.value;
+    expect(speech.stop).not.toHaveBeenCalled();
+    window.dispatchEvent(new KeyboardEvent("keyup", { key: "Meta", code: "MetaLeft" }));
+    await speech.start.mock.results[0]?.value;
+    expect(speech.stop).toHaveBeenCalledTimes(stops);
+  },
+);
+
 const escape = () =>
   new KeyboardEvent("keydown", { key: "Escape", code: "Escape", bubbles: true, cancelable: true });
 
diff --git a/apps/web/src/speech/useDictationShortcut.ts b/apps/web/src/speech/useDictationShortcut.ts
index 278a4baa60026..155a6efd68585 100644
--- a/apps/web/src/speech/useDictationShortcut.ts
+++ b/apps/web/src/speech/useDictationShortcut.ts
@@ -98,6 +98,7 @@ export function useDictationShortcut(input: ShortcutInput) {
   const pressed = useRef<{
     generation: number;
     code: string;
+    modifiers: string[];
     startedAt: number;
     mode: typeof mode;
     starting: Promise<void>;
@@ -110,7 +111,10 @@ export function useDictationShortcut(input: ShortcutInput) {
     shortcutTargets.set(id.current, () => current.current);
     const finish = (event: KeyboardEvent | null) => {
       const press = pressed.current;
-      if (!press || (event && (event.code || event.key) !== press.code)) return;
+      if (!press) return;
+      // macOS can omit the letter keyup while Command is held; releasing a chord modifier ends it too.
+      if (event && (event.code || event.key) !== press.code && !press.modifiers.includes(event.key))
+        return;
       pressed.current = null;
       if (shouldFinishDictationOnRelease(press.mode, performance.now() - press.startedAt)) {
         void press.starting.then(() => {
@@ -166,6 +170,7 @@ export function useDictationShortcut(input: ShortcutInput) {
       pressed.current = {
         generation: generation.current,
         code: event.code || event.key,
+        modifiers: ["Alt", "Control", "Meta", "Shift"].filter((key) => event.getModifierState(key)),
         startedAt: performance.now(),
         mode,
         starting: speech.start(),