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 d5ab87c82..0e9f17673 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
@@ -185,12 +185,13 @@ function ( $val ) use ( $media ) {
 	/**
 	 * Download an attachment source to the file system.
 	 *
-	 * @param int    $attachment_id The attachment ID.
-	 * @param string $source        The optional source to download.
+	 * @param int         $attachment_id The attachment ID.
+	 * @param string      $source        The optional source to download.
+	 * @param string|null $date          The date of the attachment to set storage folders.
 	 *
 	 * @return array|\WP_Error
 	 */
-	public function download_asset( $attachment_id, $source = null ) {
+	public function download_asset( $attachment_id, $source = null, $date = null ) {
 		require_once ABSPATH . 'wp-admin/includes/image.php';
 		require_once ABSPATH . 'wp-admin/includes/media.php';
 		if ( empty( $source ) ) {
@@ -200,7 +201,7 @@ public function download_asset( $attachment_id, $source = null ) {
 		$file_name = basename( $source );
 		try {
 			// Prime a file to stream to.
-			$upload = wp_upload_bits( $file_name, null, 'temp' );
+			$upload = wp_upload_bits( $file_name, null, 'temp', $date );
 			if ( ! empty( $upload['error'] ) ) {
 				return new \WP_Error( 'download_error', $upload['error'] );
 			}
diff --git a/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/sync/class-storage.php b/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/sync/class-storage.php
index f2bb63527..9cfa6cd96 100644
--- a/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/sync/class-storage.php
+++ b/cloudinary-image-management-and-manipulation-in-the-cloud-cdn/php/sync/class-storage.php
@@ -157,7 +157,15 @@ public function validate_file_folder_sync( $attachment_id ) {
 	 * @return string
 	 */
 	public function generate_signature( $attachment_id ) {
-		return $this->settings['offload'] . $this->media->get_post_meta( $attachment_id, Sync::META_KEYS['public_id'], true );
+		$file_exists = true;
+		if ( $this->settings['offload'] !== 'cld' ) {
+			$attachment_file = get_attached_file( $attachment_id );
+			if ( ! file_exists( $attachment_file ) ) {
+				$file_exists = $attachment_file;
+			}
+		}
+
+		return $this->settings['offload'] . $this->media->get_post_meta( $attachment_id, Sync::META_KEYS['public_id'], true ) . $file_exists;
 	}
 
 	/**
@@ -184,7 +192,8 @@ public function sync( $attachment_id ) {
 				$url = $this->media->cloudinary_url( $attachment_id, '', $transformations, null, false, true );
 				break;
 			case 'dual_full':
-				if ( ! empty( $previous_state ) && 'dual_full' !== $previous_state ) {
+				$exists = get_attached_file( $attachment_id );
+				if ( ! empty( $previous_state ) && ! file_exists( $exists ) ) {
 					// Only do this is it's changing a state.
 					$transformations = $this->media->get_transformation_from_meta( $attachment_id );
 					$url             = $this->media->cloudinary_url( $attachment_id, '', $transformations, null, false, false );
@@ -198,7 +207,8 @@ public function sync( $attachment_id ) {
 			if ( 'cld' !== $previous_state ) {
 				$this->remove_local_assets( $attachment_id );
 			}
-			$this->download->download_asset( $attachment_id, $url );
+			$date = get_post_datetime( $attachment_id );
+			$this->download->download_asset( $attachment_id, $url, $date->format( 'Y/m' ) );
 		}
 
 		$this->sync->set_signature_item( $attachment_id, 'storage' );