diff --git a/php/class-media.php b/php/class-media.php
index cf4a3370b..1064c15c2 100644
--- a/php/class-media.php
+++ b/php/class-media.php
@@ -1693,6 +1693,36 @@ public function has_public_id( $attachment_id ) {
 		return ! empty( $new_id ) || ! empty( $id );
 	}
 
+	/**
+	 * Check if an attachment's registered sizes reference filenames that no longer match the current attached file.
+	 *
+	 * This happens when an image is edited (e.g. cropped) via the WordPress image editor: the main file gets
+	 * renamed (an `-e{timestamp}` suffix is added), but the `sizes` metadata can be left pointing at the
+	 * pre-edit filenames, leaving no local file matching that size record.
+	 *
+	 * @param int $attachment_id The Attachment ID.
+	 *
+	 * @return bool
+	 */
+	public function has_outdated_sizes( $attachment_id ) {
+		$metadata = wp_get_attachment_metadata( $attachment_id );
+		if ( empty( $metadata['file'] ) || empty( $metadata['sizes'] ) ) {
+			return false;
+		}
+
+		$base = wp_basename( $metadata['file'] );
+		$ext  = pathinfo( $base, PATHINFO_EXTENSION );
+		$base = ! empty( $ext ) ? substr( $base, 0, - ( strlen( $ext ) + 1 ) ) : $base;
+
+		foreach ( $metadata['sizes'] as $size ) {
+			if ( empty( $size['file'] ) || 0 !== strpos( $size['file'], $base . '-' ) ) {
+				return true;
+			}
+		}
+
+		return false;
+	}
+
 	/**
 	 * Get a Cloudinary ID which includes the file format extension.
 	 *
diff --git a/php/class-sync.php b/php/class-sync.php
index 30e73015d..e9bcd7d5e 100644
--- a/php/class-sync.php
+++ b/php/class-sync.php
@@ -568,6 +568,18 @@ public function setup_sync_base_struct() {
 				'required' => false, // Required to complete URL render flag.
 				'realtime' => true,
 			),
+			'sizes'        => array(
+				'generate' => array( $this, 'generate_sizes_signature' ),
+				'priority' => 5.25,
+				'sync'     => array( $this->managers['upload'], 'regenerate_sizes' ),
+				'validate' => function ( $attachment_id ) {
+					return $this->managers['media']->has_outdated_sizes( $attachment_id );
+				},
+				'state'    => 'info syncing',
+				'note'     => __( 'Regenerating thumbnail sizes', 'cloudinary' ),
+				'required' => false,
+				'realtime' => true,
+			),
 			'folder'       => array(
 				'generate' => array( $this->managers['media'], 'get_cloudinary_folder' ),
 				'validate' => array( $this->managers['media'], 'is_folder_synced' ),
@@ -1389,4 +1401,19 @@ public function generate_edit_signature( $attachment_id ) {
 
 		return $str;
 	}
+
+	/**
+	 * Generate a signature for an attachment's thumbnail sizes.
+	 *
+	 * @param int $attachment_id The attachment ID.
+	 *
+	 * @return string
+	 */
+	public function generate_sizes_signature( $attachment_id ) {
+		$metadata = wp_get_attachment_metadata( $attachment_id );
+		$file     = ! empty( $metadata['file'] ) ? wp_basename( $metadata['file'] ) : '';
+		$sizes    = ! empty( $metadata['sizes'] ) ? wp_json_encode( $metadata['sizes'] ) : '';
+
+		return $file . $sizes;
+	}
 }
diff --git a/php/sync/class-upload-sync.php b/php/sync/class-upload-sync.php
index aa8b7f9de..2c81adfe5 100644
--- a/php/sync/class-upload-sync.php
+++ b/php/sync/class-upload-sync.php
@@ -277,6 +277,31 @@ public function edit_upload( $attachment_id ) {
 		return $this->upload_asset( $attachment_id, 'edit' );
 	}
 
+	/**
+	 * Regenerate an attachment's thumbnail sizes when they no longer match the current attached file.
+	 *
+	 * @param int $attachment_id The attachment ID.
+	 *
+	 * @return array|\WP_Error
+	 */
+	public function regenerate_sizes( $attachment_id ) {
+		if ( ! function_exists( 'wp_generate_attachment_metadata' ) ) {
+			require_once ABSPATH . 'wp-admin/includes/image.php';
+		}
+
+		$file     = get_attached_file( $attachment_id );
+		$metadata = wp_generate_attachment_metadata( $attachment_id, $file );
+		if ( empty( $metadata ) ) {
+			return new \WP_Error( 'cloudinary_regenerate_sizes_failed', __( 'Could not regenerate attachment sizes.', 'cloudinary' ) );
+		}
+
+		wp_update_attachment_metadata( $attachment_id, $metadata );
+		// Persist the new signature, otherwise this would re-trigger on every subsequent render.
+		$this->sync->set_signature_item( $attachment_id, 'sizes' );
+
+		return $metadata;
+	}
+
 	/**
 	 * Upload an asset to Cloudinary.
 	 *