diff --git a/projects/packages/videopress/changelog/update-videopress-fix-replace-when-uploading-video-issue b/projects/packages/videopress/changelog/update-videopress-fix-replace-when-uploading-video-issue
new file mode 100644
index 000000000000..9ddabc42646b
--- /dev/null
+++ b/projects/packages/videopress/changelog/update-videopress-fix-replace-when-uploading-video-issue
@@ -0,0 +1,4 @@
+Significance: patch
+Type: fixed
+
+VideoPress: fix replace video by uploading a new file issue
diff --git a/projects/packages/videopress/package.json b/projects/packages/videopress/package.json
index b92bf0739957..63dca9927d52 100644
--- a/projects/packages/videopress/package.json
+++ b/projects/packages/videopress/package.json
@@ -1,7 +1,7 @@
 {
 	"private": true,
 	"name": "@automattic/jetpack-videopress",
-	"version": "0.10.4",
+	"version": "0.10.5-alpha",
 	"description": "VideoPress package",
 	"homepage": "https://github.com/Automattic/jetpack/tree/HEAD/projects/packages/videopress/#readme",
 	"bugs": {
diff --git a/projects/packages/videopress/src/class-package-version.php b/projects/packages/videopress/src/class-package-version.php
index c2e65fd9b58d..f752770ee70b 100644
--- a/projects/packages/videopress/src/class-package-version.php
+++ b/projects/packages/videopress/src/class-package-version.php
@@ -11,7 +11,7 @@
  * The Package_Version class.
  */
 class Package_Version {
-	const PACKAGE_VERSION = '0.10.4';
+	const PACKAGE_VERSION = '0.10.5-alpha';
 
 	const PACKAGE_SLUG = 'videopress';
 
diff --git a/projects/packages/videopress/src/client/block-editor/blocks/video/components/videopress-uploader/uploader-progress.js b/projects/packages/videopress/src/client/block-editor/blocks/video/components/videopress-uploader/uploader-progress.js
index 653ef869d4eb..67b83b493be9 100644
--- a/projects/packages/videopress/src/client/block-editor/blocks/video/components/videopress-uploader/uploader-progress.js
+++ b/projects/packages/videopress/src/client/block-editor/blocks/video/components/videopress-uploader/uploader-progress.js
@@ -113,8 +113,7 @@ const usePosterAndTitleUpdate = ( { setAttributes, videoData, onDone } ) => {
 
 		Promise.allSettled( updates ).then( () => {
 			setIsFinishingUpdate( false );
-			setAttributes( videoData );
-			onDone();
+			onDone( videoData );
 		} );
 	};
 
diff --git a/projects/packages/videopress/src/client/block-editor/blocks/video/edit.tsx b/projects/packages/videopress/src/client/block-editor/blocks/video/edit.tsx
index 71fa86285ea1..7a9c9faaaff3 100644
--- a/projects/packages/videopress/src/client/block-editor/blocks/video/edit.tsx
+++ b/projects/packages/videopress/src/client/block-editor/blocks/video/edit.tsx
@@ -390,12 +390,23 @@ export default function VideoPressEdit( {
 
 	// Render uploading block view
 	if ( isUploadingFile ) {
-		const handleDoneUpload = () => {
+		const handleDoneUpload = newVideoData => {
 			setIsUploadingFile( false );
 			if ( isReplacingFile.isReplacing ) {
+				const newBlockAttributes = {
+					...attributes,
+					...newVideoData,
+				};
+
+				// Delete attributes that are not needed.
+				delete newBlockAttributes.poster;
+
 				setIsReplacingFile( { isReplacing: false, prevAttrs: {} } );
-				replaceBlock( clientId, createBlock( 'videopress/video', { ...attributes } ) );
+				replaceBlock( clientId, createBlock( 'videopress/video', newBlockAttributes ) );
+				return;
 			}
+
+			setAttributes( { id: newVideoData.id, guid: newVideoData.guid, title: newVideoData.title } );
 		};
 
 		return (
@@ -498,8 +509,12 @@ export default function VideoPressEdit( {
 						setFileToUpload( media );
 					} }
 					onSelectVideoFromLibrary={ media => {
-						const mediaGuid = media.videopress_guid?.[ 0 ] ?? media.videopress_guid;
+						// Depending on the endpoint, `videopress_guid` can be an array or a string.
+						const mediaGuid = Array.isArray( media.videopress_guid )
+							? media.videopress_guid[ 0 ]
+							: media.videopress_guid;
 						if ( ! mediaGuid ) {
+							debug( 'No media guid provided' );
 							return;
 						}