diff --git a/projects/plugins/jetpack/changelog/story-block-add-more-media-options b/projects/plugins/jetpack/changelog/story-block-add-more-media-options
new file mode 100644
index 000000000000..3eae07bed566
--- /dev/null
+++ b/projects/plugins/jetpack/changelog/story-block-add-more-media-options
@@ -0,0 +1,4 @@
+Significance: patch
+Type: other
+
+Comment: Story block: Add more media options to choose from in the editor
diff --git a/projects/plugins/jetpack/extensions/blocks/story/edit.js b/projects/plugins/jetpack/extensions/blocks/story/edit.js
index 3a77f6fc2d42..8a989e43e81c 100644
--- a/projects/plugins/jetpack/extensions/blocks/story/edit.js
+++ b/projects/plugins/jetpack/extensions/blocks/story/edit.js
@@ -24,7 +24,7 @@ import './editor.scss';
 
 const ALLOWED_MEDIA_TYPES = [ 'image', 'video' ];
 
-export const pickRelevantMediaFiles = ( media, sizeSlug = 'large' ) => {
+export const pickRelevantMediaFiles = media => {
 	const mediaProps = pick( media, [
 		'alt',
 		'title',
@@ -37,8 +37,8 @@ export const pickRelevantMediaFiles = ( media, sizeSlug = 'large' ) => {
 		'height',
 	] );
 	mediaProps.url =
-		get( media, [ 'sizes', sizeSlug, 'url' ] ) ||
-		get( media, [ 'media_details', 'sizes', sizeSlug, 'source_url' ] ) ||
+		get( media, [ 'sizes', 'large', 'url' ] ) ||
+		get( media, [ 'media_details', 'sizes', 'large', 'source_url' ] ) ||
 		get( media, [ 'media_details', 'videopress', 'original' ] ) ||
 		get( media, [ 'media_details', 'original', 'url' ] ) ||
 		media.url;
@@ -63,7 +63,16 @@ export default withNotices( function StoryEdit( {
 	const lockName = 'storyBlockLock';
 
 	const onSelectMedia = newMediaFiles => {
-		const allMedia = newMediaFiles.map( file => pickRelevantMediaFiles( file ) );
+		const allMedia = newMediaFiles
+			.map( newMedia => {
+				// MediaPlaceholder passes only the media ids as value to MediaUpload, so we're only getting those back
+				if ( ! isNaN( newMedia ) ) {
+					const existingMedia = mediaFiles.find( mediaFile => mediaFile.id === newMedia );
+					return existingMedia || { id: newMedia };
+				}
+				return newMedia;
+			} )
+			.map( pickRelevantMediaFiles );
 		const uploadedMedias = allMedia.filter( media => ! isBlobURL( media.url ) );
 		// prevent saving blob urls in mediaFiles block attribute
 		if ( allMedia.length !== uploadedMedias.length ) {
diff --git a/projects/plugins/jetpack/extensions/shared/external-media/index.js b/projects/plugins/jetpack/extensions/shared/external-media/index.js
index 7d5fac3fdb10..090cd306d115 100644
--- a/projects/plugins/jetpack/extensions/shared/external-media/index.js
+++ b/projects/plugins/jetpack/extensions/shared/external-media/index.js
@@ -36,6 +36,7 @@ if ( isCurrentUserConnected() && 'function' === typeof useBlockEditContext ) {
 			'core/media-text',
 			'jetpack/image-compare',
 			'jetpack/slideshow',
+			'jetpack/story',
 			'jetpack/tiled-gallery',
 		];