diff --git a/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/class-sync.php b/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/class-sync.php
index a2bcd3745..6d740dcd7 100644
--- a/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/class-sync.php
+++ b/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/class-sync.php
@@ -48,6 +48,7 @@ class Sync implements Setup, Assets {
 		'transformation' => '_transformations',
 		'sync_error'     => '_sync_error',
 		'cloudinary'     => '_cloudinary_v2',
+		'attempts'       => '_sync_attempts',
 	);
 
 	/**
diff --git a/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/media/class-upgrade.php b/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/media/class-upgrade.php
index f4568904f..7621769eb 100644
--- a/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/media/class-upgrade.php
+++ b/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/media/class-upgrade.php
@@ -55,6 +55,20 @@ public function check_cloudinary_version( $cloudinary_id, $attachment_id ) {
 			 */
 			if ( ! empty( $meta['cloudinary'] ) && empty( $public_id ) ) {
 				$cloudinary_id = $this->convert_cloudinary_version( $attachment_id );
+			} elseif ( ! empty( $meta['cloudinary'] ) ) {
+				// Has public ID, but still has cloudinary, check pending status.
+				$is_pending = $this->media->get_post_meta( $attachment_id, Sync::META_KEYS['pending'], true );
+				$attempts   = (int) $this->media->get_post_meta( $attachment_id, Sync::META_KEYS['attempts'], true );
+				if ( ( empty( $is_pending ) || $is_pending < time() - 5 * 60 ) && 10 > $attempts ) {
+					// Timeout.
+					$this->media->update_post_meta( $attachment_id, Sync::META_KEYS['attempts'], $attempts + 1 );
+
+					// return proposed ID to allow front render.
+					return $this->convert_cloudinary_version( $attachment_id );
+				}
+				$cloudinary_id = $public_id;
+			} else {
+				$cloudinary_id = $public_id;
 			}
 		}
 
@@ -105,6 +119,8 @@ function ( $val ) use ( $media ) {
 		$public_id = strstr( $public_id, '.' . $path['extension'], true );
 		// Save public ID.
 		$this->media->update_post_meta( $attachment_id, Sync::META_KEYS['public_id'], $public_id );
+		// Set download started data.
+		$this->media->update_post_meta( $attachment_id, Sync::META_KEYS['pending'], time() );
 
 		// Setup a call for a background sync.
 		$params = array(
@@ -125,7 +141,7 @@ public function setup_hooks() {
 		add_filter( 'cloudinary_id', array( $this, 'check_cloudinary_version' ), 9, 2 ); // Priority 9, to take preference over prep_on_demand_upload.
 
 		// Add a redirection to the new plugin settings, from the old plugin.
-		if( is_admin() ) {
+		if ( is_admin() ) {
 			add_action( 'admin_menu', function () {
 				global $plugin_page;
 				if ( ! empty( $plugin_page ) && false !== strpos( $plugin_page, 'cloudinary-image-management-and-manipulation-in-the-cloud-cdn' ) ) {
diff --git a/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/sync/class-download-sync.php b/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/sync/class-download-sync.php
index cda52be93..92de295ba 100644
--- a/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/sync/class-download-sync.php
+++ b/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/sync/class-download-sync.php
@@ -7,6 +7,8 @@
 
 namespace Cloudinary\Sync;
 
+use Cloudinary\Sync;
+
 /**
  * Class Download_Sync.
  *
@@ -88,9 +90,15 @@ public function rest_can_upload_files( \WP_REST_Request $request ) {
 	 */
 	public function handle_failed_download( $attachment_id, $error ) {
 		// @todo: Place a handler to catch the error for logging.
-		// Delete attachment temp.
-		wp_delete_attachment( $attachment_id, true );
 
+		$is_pending = $this->plugin->components['media']->get_post_meta( $attachment_id, Sync::META_KEYS['pending'], true );
+		if ( ! empty( $is_pending ) ) {
+			// Dont delete if it's a downsync.
+			$this->plugin->components['media']->update_post_meta( $attachment_id, Sync::META_KEYS['sync_error'], $error );
+		} else {
+			// Delete attachment temp.
+			wp_delete_attachment( $attachment_id, true );
+		}
 		// Send error.
 		wp_send_json_error( $error );
 	}
@@ -181,6 +189,10 @@ public function rest_download_asset( \WP_REST_Request $request ) {
 			'data'    => $attachment,
 		);
 
+		// Remove pending.
+		delete_post_meta( $attachment_id, Sync::META_KEYS['pending'] );
+		delete_post_meta( $attachment_id, Sync::META_KEYS['sync_error'] );
+
 		return rest_ensure_response( $response );
 	}
 }