diff --git a/electron/windows.ts b/electron/windows.ts
index 687a3a175..0b19d5b98 100644
--- a/electron/windows.ts
+++ b/electron/windows.ts
@@ -264,7 +264,22 @@ export function createHudOverlayWindow(): BrowserWindow {
 			backgroundThrottling: false,
 		},
 	});
-	win.setIgnoreMouseEvents(true, { forward: true });
+
+	// Deliberately NOT born click-through: the renderer asks for it on mount, over
+	// "hud-overlay-ignore-mouse-events" (`show: false` holds this window back until
+	// ready-to-show, so the two are ~85 ms apart — measured, not assumed). What that
+	// leaves open is an invisible rectangle that can swallow one desktop click in
+	// those 85 ms, right after the user launched the app — against what doing it here
+	// cost them: the whole app (issue #266). On Windows the `forward` option is a global
+	// WH_MOUSE_LL hook, and that hook is the only way out of the state, because
+	// Chromium sends no pointermove to a window it has made input-transparent — so
+	// the renderer can never ask to leave it on its own. Electron latches
+	// the install behind `forwarding_mouse_messages_` and retries only after a
+	// setIgnoreMouseEvents(false) — the very call a dead hook prevents. One refused
+	// or revoked hook (Windows drops any whose callback overruns the 300 ms
+	// LowLevelHooksTimeout — on this thread, still busy booting the app) and the HUD
+	// is painted, inert, forever. Asking later moves the install onto an IPC message,
+	// i.e. onto a main thread that is provably pumping.
 
 	// Keep the recording controls out of the recording (see applyContentProtection).
 	applyContentProtection(win, "HUD");
diff --git a/tests/e2e/windows-native-checklist.spec.ts b/tests/e2e/windows-native-checklist.spec.ts
index 9c9c5710e..959b15f1d 100644
--- a/tests/e2e/windows-native-checklist.spec.ts
+++ b/tests/e2e/windows-native-checklist.spec.ts
@@ -319,4 +319,80 @@ test.describe("Windows native checklist smoke tests", () => {
 			}
 		}
 	});
+
+	// The HUD must reach click-through by *asking* for it from the renderer, never
+	// by being born that way. On Windows the `forward` option is a global
+	// WH_MOUSE_LL hook, and it is the only route back out: a HUD that is already
+	// input-transparent when the hook fails to install can never be clicked again,
+	// which is what bricked the app in issue #266. Both halves matter — that nothing
+	// asks during construction, and that the renderer still does after mount.
+	test("the HUD asks for click-through instead of being born with it", async () => {
+		const app = await launchApp();
+
+		try {
+			const hudWindow = await app.firstWindow({ timeout: 60_000 });
+			await hudWindow.waitForLoadState("domcontentloaded");
+			await dismissLanguagePrompt(hudWindow);
+
+			// A second window keeps the window list non-empty while the HUD is torn
+			// down below — emptying it fires window-all-closed, which quits the app.
+			await hudWindow.getByTestId("launch-source-selector-button").click();
+			await app.waitForEvent("window", {
+				predicate: (w) => w.url().includes("windowType=source-selector"),
+				timeout: 15_000,
+			});
+
+			// Recreate the HUD through the app's own path (second-instance →
+			// showMainWindow → createHudOverlayWindow) with the native call taped.
+			// Nothing awaits between the tape going on and the snapshot coming off,
+			// so no IPC from the renderer can slip into it: what comes back is
+			// construction, and construction only.
+			const duringConstruction = await app.evaluate(({ app: electronApp, BrowserWindow }) => {
+				const tape: unknown[][] = [];
+				const original = BrowserWindow.prototype.setIgnoreMouseEvents;
+				globalThis.__hudTape = tape;
+				globalThis.__hudSetIgnoreMouseEvents = original;
+				BrowserWindow.prototype.setIgnoreMouseEvents = function patched(
+					this: InstanceType<typeof BrowserWindow>,
+					...args: Parameters<typeof original>
+				) {
+					tape.push(args);
+					return original.apply(this, args);
+				};
+
+				BrowserWindow.getAllWindows()
+					.find((w) => w.webContents.getURL().includes("windowType=hud-overlay"))
+					?.destroy();
+				electronApp.emit("second-instance");
+
+				return tape.slice();
+			});
+
+			expect(duringConstruction).toEqual([]);
+
+			// And the renderer does ask, once it has mounted.
+			await expect
+				.poll(() => app.evaluate(() => globalThis.__hudTape ?? []), { timeout: 20_000 })
+				.toContainEqual([true, { forward: true }]);
+		} finally {
+			await app.evaluate(({ BrowserWindow }) => {
+				const original = globalThis.__hudSetIgnoreMouseEvents;
+				if (original) {
+					BrowserWindow.prototype.setIgnoreMouseEvents = original;
+				}
+				globalThis.__hudTape = undefined;
+				globalThis.__hudSetIgnoreMouseEvents = undefined;
+			});
+			await closeApp(app);
+		}
+	});
 });
+
+declare global {
+	// Set inside the main process by the click-through test above, read back by a
+	// second evaluate — the only way to observe calls that land between two of them.
+	var __hudTape: unknown[][] | undefined;
+	var __hudSetIgnoreMouseEvents:
+		| ((ignore: boolean, options?: { forward?: boolean }) => void)
+		| undefined;
+}