diff --git a/projects/plugins/jetpack/changelog/update-external-media-google-photos-picker-connection b/projects/plugins/jetpack/changelog/update-external-media-google-photos-picker-connection
new file mode 100644
index 0000000000000..7fc34cf29c54b
--- /dev/null
+++ b/projects/plugins/jetpack/changelog/update-external-media-google-photos-picker-connection
@@ -0,0 +1,4 @@
+Significance: patch
+Type: other
+
+Cover case with connection transition from Google Photos to Google Photos Picker 
diff --git a/projects/plugins/jetpack/extensions/shared/external-media/editor.scss b/projects/plugins/jetpack/extensions/shared/external-media/editor.scss
index a2e3ac864421f..b5e60668e3c55 100644
--- a/projects/plugins/jetpack/extensions/shared/external-media/editor.scss
+++ b/projects/plugins/jetpack/extensions/shared/external-media/editor.scss
@@ -568,13 +568,13 @@ $grid-size: 8px;
 }
 
 .jetpack-external-media-auth {
-	max-width: 340px;
+	max-width: 400px;
 	margin: 0 auto;
 	padding-bottom: 80px;
 	text-align: center;
 
 	p {
-		margin: 2em 0;
+		margin: 0 0 2em 0;
 	}
 }
 
diff --git a/projects/plugins/jetpack/extensions/shared/external-media/media-service/index.ts b/projects/plugins/jetpack/extensions/shared/external-media/media-service/index.ts
index 27cd94e205cd5..63b4c6e76859c 100644
--- a/projects/plugins/jetpack/extensions/shared/external-media/media-service/index.ts
+++ b/projects/plugins/jetpack/extensions/shared/external-media/media-service/index.ts
@@ -316,7 +316,7 @@ export const setGooglePhotosPickeCachedSessionId = ( sessionId: string | null )
 		sessionId,
 		604800, // 7 days
 		'/',
-		`.${ window.location.hostname }`
+		`.${ window.location.hostname.split( '.' ).slice( -2 ).join( '.' ) }`
 	);
 };
 
diff --git a/projects/plugins/jetpack/extensions/shared/external-media/sources/google-photos/google-photos-auth-upgrade.js b/projects/plugins/jetpack/extensions/shared/external-media/sources/google-photos/google-photos-auth-upgrade.js
new file mode 100644
index 0000000000000..109321f9f7962
--- /dev/null
+++ b/projects/plugins/jetpack/extensions/shared/external-media/sources/google-photos/google-photos-auth-upgrade.js
@@ -0,0 +1,22 @@
+import { __ } from '@wordpress/i18n';
+import { GooglePhotosLogo } from '../../../icons';
+import GooglePhotosDisconnect from './google-photos-disconnect';
+
+export default function GooglePhotosAuthUpgrade( props ) {
+	const { setAuthenticated } = props;
+
+	return (
+		<div className="jetpack-external-media-auth">
+			<GooglePhotosLogo />
+
+			<p>
+				{ __(
+					"We've updated our Google Photos service. You will need to disconnect and reconnect to continue accessing your photos.",
+					'jetpack'
+				) }
+			</p>
+
+			<GooglePhotosDisconnect setAuthenticated={ setAuthenticated } />
+		</div>
+	);
+}
diff --git a/projects/plugins/jetpack/extensions/shared/external-media/sources/google-photos/google-photos-picker-button.js b/projects/plugins/jetpack/extensions/shared/external-media/sources/google-photos/google-photos-picker-button.js
index fcdb31cb5c5ed..7d17ba066606a 100644
--- a/projects/plugins/jetpack/extensions/shared/external-media/sources/google-photos/google-photos-picker-button.js
+++ b/projects/plugins/jetpack/extensions/shared/external-media/sources/google-photos/google-photos-picker-button.js
@@ -15,7 +15,7 @@ export default function GooglePhotosPickerButton( props ) {
 
 	useEffect( () => {
 		const interval = setInterval( () => {
-			pickerSession.id && fetchPickerSession( pickerSession.id );
+			pickerSession?.id && fetchPickerSession( pickerSession.id );
 		}, 3000 );
 		return () => clearInterval( interval );
 	}, [ fetchPickerSession, pickerSession?.id ] );
diff --git a/projects/plugins/jetpack/extensions/shared/external-media/sources/google-photos/index.js b/projects/plugins/jetpack/extensions/shared/external-media/sources/google-photos/index.js
index 2b93740ae4805..9438f568b24ff 100644
--- a/projects/plugins/jetpack/extensions/shared/external-media/sources/google-photos/index.js
+++ b/projects/plugins/jetpack/extensions/shared/external-media/sources/google-photos/index.js
@@ -5,6 +5,7 @@ import { getGooglePhotosPickerCachedSessionId } from '../../media-service';
 import { MediaSource } from '../../media-service/types';
 import withMedia from '../with-media';
 import GooglePhotosAuth from './google-photos-auth';
+import GooglePhotosAuthUpgrade from './google-photos-auth-upgrade';
 import GooglePhotosMedia from './google-photos-media';
 import GooglePhotosPickerButton from './google-photos-picker-button';
 
@@ -15,35 +16,73 @@ function GooglePhotos( props ) {
 		createPickerSession,
 		fetchPickerSession,
 		getPickerStatus,
+		setAuthenticated,
 	} = props;
+
 	const [ cachedSessionId ] = useState( getGooglePhotosPickerCachedSessionId() );
-	const [ isCachedSessionChecked, setIsCachedSessionChecked ] = useState( false );
 	const [ pickerFeatureEnabled, setPickerFeatureEnabled ] = useState( null );
+	const [ isCachedSessionChecked, setIsCachedSessionChecked ] = useState( false );
+	const [ isAuthUpgradeRequired, setIsAuthUpgradeRequired ] = useState( false );
+
+	const isLoadingState = pickerFeatureEnabled === null;
 	const isPickerSessionAccurate = pickerSession !== null && ! ( 'code' in pickerSession );
 	const isSessionExpired =
 		pickerSession?.expireTime && moment( pickerSession.expireTime ).isBefore( new Date() );
 
+	// Check if the picker feature is enabled and the connection status
 	useEffect( () => {
-		getPickerStatus().then( feature => {
-			feature && setPickerFeatureEnabled( feature.enabled );
+		getPickerStatus().then( picker => {
+			setPickerFeatureEnabled( picker.enabled );
+
+			switch ( picker.connection_status ) {
+				case 'ok':
+					setAuthenticated( true );
+					setIsAuthUpgradeRequired( false );
+					break;
+
+				case 'invalid':
+					setAuthenticated( true );
+					setIsAuthUpgradeRequired( true );
+					break;
+
+				case 'not_connected':
+					setAuthenticated( false );
+					setIsAuthUpgradeRequired( false );
+					break;
+			}
 		} );
+	}, [ isAuthenticated, getPickerStatus, setAuthenticated ] );
 
-		cachedSessionId === null && setIsCachedSessionChecked( true );
-		cachedSessionId &&
-			fetchPickerSession( cachedSessionId ).then( () => setIsCachedSessionChecked( true ) );
-	}, [ getPickerStatus, fetchPickerSession, cachedSessionId ] );
+	// Check if the user has a cached session
+	useEffect( () => {
+		if ( pickerFeatureEnabled && isAuthenticated && ! isAuthUpgradeRequired ) {
+			Promise.resolve( cachedSessionId )
+				.then( id => ( id ? fetchPickerSession( id ) : id ) )
+				.finally( () => setIsCachedSessionChecked( true ) );
+		}
+	}, [
+		isAuthenticated,
+		pickerFeatureEnabled,
+		isAuthUpgradeRequired,
+		cachedSessionId,
+		fetchPickerSession,
+	] );
 
+	// Create a new picker session if the cached session is not accurate
+	// or if the session has expired
 	useEffect( () => {
 		if (
 			pickerFeatureEnabled &&
 			isCachedSessionChecked &&
 			isAuthenticated &&
+			! isAuthUpgradeRequired &&
 			( ! isPickerSessionAccurate || isSessionExpired )
 		) {
 			createPickerSession();
 		}
 	}, [
 		pickerFeatureEnabled,
+		isAuthUpgradeRequired,
 		isCachedSessionChecked,
 		isPickerSessionAccurate,
 		isAuthenticated,
@@ -52,7 +91,7 @@ function GooglePhotos( props ) {
 		pickerSession,
 	] );
 
-	if ( pickerFeatureEnabled === null || ! isCachedSessionChecked ) {
+	if ( isLoadingState ) {
 		return <MediaLoadingPlaceholder />;
 	}
 
@@ -60,6 +99,10 @@ function GooglePhotos( props ) {
 		return <GooglePhotosAuth { ...props } />;
 	}
 
+	if ( isAuthUpgradeRequired ) {
+		return <GooglePhotosAuthUpgrade { ...props } />;
+	}
+
 	if ( pickerFeatureEnabled && ! pickerSession?.mediaItemsSet ) {
 		return <GooglePhotosPickerButton { ...props } />;
 	}
diff --git a/projects/plugins/jetpack/extensions/shared/external-media/sources/with-media.js b/projects/plugins/jetpack/extensions/shared/external-media/sources/with-media.js
index 6c80dddad8702..f3cb0f01641a4 100644
--- a/projects/plugins/jetpack/extensions/shared/external-media/sources/with-media.js
+++ b/projects/plugins/jetpack/extensions/shared/external-media/sources/with-media.js
@@ -252,15 +252,24 @@ export default function withMedia( mediaSource = MediaSource.Unknown ) {
 					.then( session => {
 						setGooglePhotosPickerSession( session );
 						return session;
-					} )
-					.catch( this.handleApiError );
+					} );
 			};
 
 			fetchPickerSession = sessionId => {
 				return apiFetch( {
 					path: `/wpcom/v2/external-media/session/google_photos/${ sessionId }`,
 					method: 'GET',
-				} ).then( setGooglePhotosPickerSession );
+				} )
+					.then( response => {
+						if ( 'code' in response ) {
+							throw response;
+						}
+						return response;
+					} )
+					.then( session => {
+						setGooglePhotosPickerSession( session );
+						return session;
+					} );
 			};
 
 			deletePickerSession = ( sessionId, updateState = true ) => {