Redirect users to /domains/add when cart is cleared in EmailUpsell flow.

client/layout/masterbar/checkout.tsx

@@ -54,12 +54,13 @@ const CheckoutMasterbar = ( {
 	const { responseCart, replaceProductsInCart } = useShoppingCart( cartKey );
 	const [ isModalVisible, setIsModalVisible ] = useState( false );
 
-	const closeAndLeave = () =>
+	const closeAndLeave = ( options?: { userHasClearedCart?: boolean } ) =>
 		leaveCheckout( {
 			siteSlug,
 			forceCheckoutBackUrl,
 			previousPath,
 			tracksEvent: 'calypso_masterbar_close_clicked',
+			userHasClearedCart: options?.userHasClearedCart ?? false,
 		} );
 
 	const clickClose = () => {
@@ -78,7 +79,9 @@ const CheckoutMasterbar = ( {
 	const modalSecondaryText = translate( 'Empty cart' );
 	const clearCartAndLeave = () => {
 		replaceProductsInCart( [] );
-		closeAndLeave();
+		closeAndLeave( {
+			userHasClearedCart: true,
+		} );
 	};
 
 	const showCloseButton = isLeavingAllowed && checkoutType === 'wpcom';

client/my-sites/checkout/src/hooks/use-remove-from-cart-and-redirect.ts

@@ -29,6 +29,7 @@ export default function useRemoveFromCartAndRedirect(
 			createUserAndSiteBeforeTransaction,
 			previousPath: customizedPreviousPath || previousPath,
 			tracksEvent: 'calypso_empty_cart_redirect',
+			userHasClearedCart: true,
 		} );
 	}, [
 		createUserAndSiteBeforeTransaction,

client/my-sites/checkout/src/lib/leave-checkout.ts

@@ -16,18 +16,47 @@ import { sendMessageToOpener } from './popup';
 
 const debug = debugFactory( 'calypso:leave-checkout' );
 
+const getCloseURL = ( {
+	userHasClearedCart,
+	previousPath,
+	siteSlug,
+}: {
+	userHasClearedCart: boolean;
+	previousPath?: string;
+	siteSlug?: string;
+} ): string => {
+	if (
+		previousPath &&
+		previousPath !== '' &&
+		previousPath !== window.location.href &&
+		! previousPath.includes( '/checkout/' )
+	) {
+		/* Regex to match /domains/add/abc123/email/def456? */
+		const emailUpsellRegex = /\/domains\/add\/[^/]+\/email\/[^/]+(\?|\/|$)/;
+
+		if ( userHasClearedCart && emailUpsellRegex.test( previousPath ) ) {
+			return '/domains/add/' + siteSlug;
+		}
+		return previousPath;
+	}
+
+	return siteSlug ? '/plans/' + siteSlug : '/start';
+};
+
 export const leaveCheckout = ( {
 	siteSlug,
 	forceCheckoutBackUrl,
 	previousPath,
 	tracksEvent,
 	createUserAndSiteBeforeTransaction,
+	userHasClearedCart = false,
 }: {
 	siteSlug?: string;
 	forceCheckoutBackUrl?: string;
 	previousPath?: string;
 	tracksEvent: string;
 	createUserAndSiteBeforeTransaction?: boolean;
+	userHasClearedCart?: boolean;
 } ): void => {
 	recordTracksEvent( tracksEvent );
 	debug( 'leaving checkout with args', {
@@ -68,16 +97,7 @@ export const leaveCheckout = ( {
 		return;
 	}
 
-	let closeUrl = siteSlug ? '/plans/' + siteSlug : '/start';
-
-	if (
-		previousPath &&
-		'' !== previousPath &&
-		previousPath !== window.location.href &&
-		! previousPath.includes( '/checkout/' )
-	) {
-		closeUrl = previousPath;
-	}
+	const closeUrl = getCloseURL( { userHasClearedCart, previousPath, siteSlug } );
 
 	try {
 		const searchParams = new URLSearchParams( window.location.search );

client/my-sites/checkout/src/test/leave-checkout.ts

@@ -62,6 +62,69 @@ describe( 'leaveCheckout', () => {
 			expect( navigate ).not.toHaveBeenCalledWith( '/\\example.com' );
 		} );
 	} );
+
+	describe( 'getCloseURL handling', () => {
+		it( 'returns to plans page when previous path is empty', () => {
+			const siteSlug = 'mywpsite.wordpress.com';
+
+			leaveCheckout( {
+				siteSlug: siteSlug,
+				tracksEvent: 'checkout_cancel',
+				userHasClearedCart: true,
+			} );
+
+			expect( navigate ).toHaveBeenCalledWith( `/plans/${ siteSlug }` );
+		} );
+
+		it( 'returns to /start if missing site slug', () => {
+			leaveCheckout( {
+				tracksEvent: 'checkout_cancel',
+				userHasClearedCart: true,
+			} );
+
+			expect( navigate ).toHaveBeenCalledWith( '/start' );
+		} );
+
+		it( 'returns to domain page when previous page is email upsell and cart is emptied', () => {
+			const siteSlug = 'mywpsite.wordpress.com';
+
+			leaveCheckout( {
+				siteSlug: siteSlug,
+				tracksEvent: 'checkout_cancel',
+				previousPath: '/domains/add/my-search-domain/email/mywpsite.wordpress.com?',
+				userHasClearedCart: true,
+			} );
+
+			expect( navigate ).toHaveBeenCalledWith( `/domains/add/${ siteSlug }` );
+		} );
+
+		it( 'returns to previousPath', () => {
+			const previousPath = `/previous-path`;
+
+			leaveCheckout( {
+				tracksEvent: 'checkout_cancel',
+				previousPath: previousPath,
+				userHasClearedCart: false,
+			} );
+
+			expect( navigate ).toHaveBeenCalledWith( previousPath );
+		} );
+
+		it( 'returns to previousPath if email upsell and cart is not emptied', () => {
+			const siteSlug = 'mywpsite.wordpress.com';
+			const domain = 'my-search-domain';
+			const previousPath = `/domains/add/${ domain }/email/${ siteSlug }?`;
+
+			leaveCheckout( {
+				siteSlug: siteSlug,
+				tracksEvent: 'checkout_cancel',
+				previousPath: previousPath,
+				userHasClearedCart: false,
+			} );
+
+			expect( navigate ).toHaveBeenCalledWith( previousPath );
+		} );
+	} );
 } );
 
 describe( 'isRelativeUrl', () => {