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/updater.ts b/electron/updater.ts
index 8fb24177..86c2d76d 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);
 }
@@ -576,12 +580,19 @@ async function showAvailableUpdateDialog(
 	getMainWindow: () => BrowserWindow | null,
 	version: string,
 	sendToRenderer?: UpdateToastSender,
+	options?: { isPreview?: boolean; isExperimental?: boolean },
 ) {
+	const isPreview = Boolean(options?.isPreview);
+	const isExperimental = options?.isExperimental ?? getExperimentalUpdatesEnabled();
 	const result = await showMessageBox(getMainWindow, {
 		type: "info",
-		title: "Update Available",
-		message: `Recordly ${version} is available.`,
-		detail: "Install and restart now, or remind me later.",
+		title: isExperimental ? "Experimental Update Available" : "Update Available",
+		message: `Recordly ${version} is available${isExperimental ? " on the experimental channel" : ""}.`,
+		detail: isPreview
+			? `${isExperimental ? EXPERIMENTAL_UPDATE_DESCRIPTION : "This is a development preview of the standard update flow."} No real update will be installed.`
+			: isExperimental
+				? EXPERIMENTAL_UPDATE_DESCRIPTION
+				: "Install and restart now, or remind me later.",
 		buttons: ["Install & Restart", "Later"],
 		defaultId: 0,
 		cancelId: 1,
@@ -589,10 +600,24 @@ async function showAvailableUpdateDialog(
 	});
 
 	if (result.response === 0) {
+		if (isPreview) {
+			await showMessageBox(getMainWindow, {
+				type: "info",
+				title: "Preview Only",
+				message: "No real update was installed.",
+				detail: "This was only a manual development preview of the update prompt.",
+			});
+			return;
+		}
+
 		await downloadAvailableUpdate(sendToRenderer, { installAfterDownload: true });
 		return;
 	}
 
+	if (isPreview) {
+		return;
+	}
+
 	deferUpdateReminder(getMainWindow, sendToRenderer, UPDATE_REMINDER_DELAY_MS);
 }
 
@@ -644,6 +669,29 @@ async function showDownloadedUpdateDialog(
 	}
 }
 
+export function previewNativeUpdateDialog(getMainWindow: () => BrowserWindow | null) {
+	return showAvailableUpdateDialog(getMainWindow, DEV_UPDATE_PREVIEW_VERSION, undefined, {
+		isPreview: true,
+		isExperimental: DEV_UPDATE_PREVIEW_IS_EXPERIMENTAL,
+	});
+}
+
+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 +793,8 @@ 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 +857,13 @@ export function setupAutoUpdates(
 			downloadInProgress = false;
 			downloadToastDismissed = false;
 			installAfterDownloadRequested = false;
-			emitUpdateToastState(
+			const shownInRenderer = emitUpdateToastState(
 				sendToRenderer,
 				createUpdateErrorToastPayload(availableVersion, error),
 			);
+			if (!shownInRenderer) {
+				void showUpdateErrorDialog(getMainWindow, availableVersion, error);
+			}
 		}
 	});