diff --git a/electron/main.ts b/electron/main.ts
index eb640251..3514c1eb 100644
--- a/electron/main.ts
+++ b/electron/main.ts
@@ -39,6 +39,7 @@ import {
 	getUpdaterLogPath,
 	getUpdateStatusSummary,
 	installDownloadedUpdateNow,
+	previewNativeUpdateDialog,
 	previewUpdateToast,
 	setExperimentalUpdatesEnabled,
 	setupAutoUpdates,
@@ -592,6 +593,10 @@ function syncDockIcon() {
 }
 
 function sendUpdateToastToWindows(channel: "update-toast-state", payload: unknown) {
+	if (process.platform !== "darwin") {
+		return false;
+	}
+
 	if (!payload) {
 		const existingWindow = getUpdateToastWindow();
 		if (existingWindow) {
@@ -683,7 +688,12 @@ ipcMain.handle("set-experimental-updates-enabled", async (_event, enabled: unkno
 	}
 });
 
-ipcMain.handle("preview-update-toast", () => {
+ipcMain.handle("preview-update-toast", async () => {
+	if (process.platform !== "darwin") {
+		await previewNativeUpdateDialog(getUpdateDialogWindow);
+		return { success: true };
+	}
+
 	return { success: previewUpdateToast(sendUpdateToastToWindows) };
 });
 
@@ -1035,7 +1045,12 @@ app.whenReady().then(async () => {
 	setupAutoUpdates(getUpdateDialogWindow, sendUpdateToastToWindows);
 	if (IS_DEV && process.env.RECORDLY_DEV_PREVIEW_UPDATE === "1") {
 		setTimeout(() => {
-			previewUpdateToast(sendUpdateToastToWindows);
+			if (process.platform === "darwin") {
+				previewUpdateToast(sendUpdateToastToWindows);
+				return;
+			}
+
+			void previewNativeUpdateDialog(getUpdateDialogWindow);
 		}, 750);
 	}
 
diff --git a/electron/updateToastWindowOptions.test.ts b/electron/updateToastWindowOptions.test.ts
deleted file mode 100644
index 64934a84..00000000
--- a/electron/updateToastWindowOptions.test.ts
+++ /dev/null
@@ -1,18 +0,0 @@
-import { describe, expect, it } from "vitest";
-import { getUpdateToastWindowAppearance } from "./updateToastWindowOptions";
-
-describe("update toast window appearance", () => {
-	it("uses native transparency on macOS", () => {
-		expect(getUpdateToastWindowAppearance("darwin")).toEqual({
-			transparent: true,
-			backgroundColor: "#00000000",
-		});
-	});
-
-	it.each(["win32", "linux"] as const)("uses a visible opaque fallback on %s", (platform) => {
-		expect(getUpdateToastWindowAppearance(platform)).toEqual({
-			transparent: false,
-			backgroundColor: "#101418",
-		});
-	});
-});
diff --git a/electron/updateToastWindowOptions.ts b/electron/updateToastWindowOptions.ts
deleted file mode 100644
index b2253f20..00000000
--- a/electron/updateToastWindowOptions.ts
+++ /dev/null
@@ -1,8 +0,0 @@
-export function getUpdateToastWindowAppearance(platform: NodeJS.Platform) {
-	const transparent = platform === "darwin";
-
-	return {
-		transparent,
-		backgroundColor: transparent ? "#00000000" : "#101418",
-	};
-}
diff --git a/electron/updater.ts b/electron/updater.ts
index 8fb24177..206900f5 100644
--- a/electron/updater.ts
+++ b/electron/updater.ts
@@ -173,6 +173,10 @@ function showMessageBox(
 	getMainWindow: () => BrowserWindow | null,
 	options: MessageBoxOptions,
 ): Promise<MessageBoxReturnValue> {
+	if (process.platform !== "darwin") {
+		return dialog.showMessageBox(options);
+	}
+
 	const window = getDialogWindow(getMainWindow);
 	return window ? dialog.showMessageBox(window, options) : dialog.showMessageBox(options);
 }
@@ -644,6 +648,28 @@ async function showDownloadedUpdateDialog(
 	}
 }
 
+export function previewNativeUpdateDialog(getMainWindow: () => BrowserWindow | null) {
+	return showDownloadedUpdateDialog(getMainWindow, DEV_UPDATE_PREVIEW_VERSION, {
+		isPreview: true,
+	});
+}
+
+async function showUpdateErrorDialog(
+	getMainWindow: () => BrowserWindow | null,
+	version: string,
+	error: unknown,
+) {
+	await showMessageBox(getMainWindow, {
+		type: "error",
+		title: "Update Failed",
+		message: `Recordly ${version} could not be downloaded.`,
+		detail: String(error),
+		buttons: ["OK"],
+		defaultId: 0,
+		noLink: true,
+	});
+}
+
 export async function checkForAppUpdates(
 	getMainWindow: () => BrowserWindow | null,
 	options?: { manual?: boolean },
@@ -745,10 +771,8 @@ export function setupAutoUpdates(
 			return;
 		}
 
-		if (manualCheckRequested) {
-			void showAvailableUpdateDialog(getMainWindow, info.version, sendToRenderer);
-			manualCheckRequested = false;
-		}
+		void showAvailableUpdateDialog(getMainWindow, info.version, sendToRenderer);
+		manualCheckRequested = false;
 	});
 
 	autoUpdater.on("update-not-available", () => {
@@ -811,10 +835,13 @@ export function setupAutoUpdates(
 			downloadInProgress = false;
 			downloadToastDismissed = false;
 			installAfterDownloadRequested = false;
-			emitUpdateToastState(
+			const shownInRenderer = emitUpdateToastState(
 				sendToRenderer,
 				createUpdateErrorToastPayload(availableVersion, error),
 			);
+			if (!shownInRenderer) {
+				void showUpdateErrorDialog(getMainWindow, availableVersion, error);
+			}
 		}
 	});
 
diff --git a/electron/windows.ts b/electron/windows.ts
index 7579beaf..47e90b8f 100644
--- a/electron/windows.ts
+++ b/electron/windows.ts
@@ -12,7 +12,6 @@ import {
 } from "./hudOverlayBounds";
 import { getHudOverlayTaskbarOptions } from "./hudOverlayWindowOptions";
 import { getPackagedRendererBaseUrl } from "./rendererServer";
-import { getUpdateToastWindowAppearance } from "./updateToastWindowOptions";
 
 const electronWindowsDir = path.dirname(fileURLToPath(import.meta.url));
 const nodeRequire = createRequire(import.meta.url);
@@ -690,7 +689,6 @@ export function setHudOverlayRecordingActive(recording: boolean): void {
 
 export function createUpdateToastWindow(): BrowserWindow {
 	const initialBounds = getUpdateToastBounds();
-	const appearance = getUpdateToastWindowAppearance(process.platform);
 
 	const win = new BrowserWindow({
 		width: initialBounds.width,
@@ -698,14 +696,14 @@ export function createUpdateToastWindow(): BrowserWindow {
 		x: initialBounds.x,
 		y: initialBounds.y,
 		frame: false,
-		transparent: appearance.transparent,
+		transparent: true,
 		resizable: false,
 		alwaysOnTop: true,
 		skipTaskbar: true,
 		hasShadow: false,
 		show: false,
 		focusable: true,
-		backgroundColor: appearance.backgroundColor,
+		backgroundColor: "#00000000",
 		webPreferences: {
 			preload: path.join(electronWindowsDir, "preload.mjs"),
 			nodeIntegration: false,