diff --git a/inc/media_offload.php b/inc/media_offload.php
index cd66df44..b12ca246 100644
--- a/inc/media_offload.php
+++ b/inc/media_offload.php
@@ -161,8 +161,14 @@ public static function instance() {
 				self::$instance->init();
 			}
 			if ( self::$instance->settings->is_offload_enabled() ) {
+				// While a rollback runs, offloaded images are still served from Optimole, but new uploads
+				// stay local: offloading them and their filename deduplication needs offload_media on.
+				$offload_new_uploads = self::$instance->settings->get( 'offload_media' ) === 'enabled';
+
 				add_filter( 'image_downsize', [ self::$instance, 'generate_filter_downsize_urls' ], 10, 3 );
-				add_filter( 'wp_generate_attachment_metadata', [ self::$instance, 'generate_image_meta' ], 10, 2 );
+				if ( $offload_new_uploads ) {
+					add_filter( 'wp_generate_attachment_metadata', [ self::$instance, 'generate_image_meta' ], 10, 2 );
+				}
 				add_filter( 'wp_get_attachment_url', [ self::$instance, 'get_image_attachment_url' ], - 999, 2 );
 				add_filter( 'wp_insert_post_data', [ self::$instance, 'filter_uploaded_images' ] );
 
@@ -176,12 +182,15 @@ public static function instance() {
 				add_filter( 'wp_calculate_image_srcset', [ self::$instance, 'calculate_image_srcset' ], 1, 5 );
 				add_action( 'post_updated', [ self::$instance, 'update_offload_meta' ], 10, 3 );
 
-				// Backwards compatibility for older versions of WordPress < 6.0.0 requiring 3 parameters for this specific filter.
-				$below_6_0_0 = version_compare( get_bloginfo( 'version' ), '6.0.0', '<' );
-				if ( $below_6_0_0 ) {
-					add_filter( 'wp_insert_attachment_data', [ self::$instance, 'insert_legacy' ], 10, 3 );
-				} else {
-					add_filter( 'wp_insert_attachment_data', [ self::$instance, 'insert' ], 10, 4 );
+				// Local uploads keep WordPress's own filename deduplication.
+				if ( $offload_new_uploads ) {
+					// Backwards compatibility for older versions of WordPress < 6.0.0 requiring 3 parameters for this specific filter.
+					$below_6_0_0 = version_compare( get_bloginfo( 'version' ), '6.0.0', '<' );
+					if ( $below_6_0_0 ) {
+						add_filter( 'wp_insert_attachment_data', [ self::$instance, 'insert_legacy' ], 10, 3 );
+					} else {
+						add_filter( 'wp_insert_attachment_data', [ self::$instance, 'insert' ], 10, 4 );
+					}
 				}
 
 				add_action( 'optml_start_processing_images', [ self::$instance, 'start_processing_images' ], 10, 6 );
diff --git a/tests/test-media.php b/tests/test-media.php
index 529b5373..37e5d63b 100644
--- a/tests/test-media.php
+++ b/tests/test-media.php
@@ -224,6 +224,31 @@ static function unlinkRecursive( $pattern, $files ) {
 			}
 		}
 	}
+	/**
+	 * While a rollback runs (offload_media off, rollback_status on), offloaded images are still
+	 * served from Optimole, but a new upload stays in the media library.
+	 */
+	public function test_upload_during_rollback_stays_local(): void {
+		$settings = new Optml_Settings();
+		$settings->update( 'offload_media', 'disabled' );
+		$settings->update( 'rollback_status', 'enabled' );
+
+		// The hooks of this request, registered with the rollback state.
+		remove_all_filters( 'wp_generate_attachment_metadata' );
+		remove_all_filters( 'wp_insert_attachment_data' );
+		Optml_Media_Offload::instance();
+
+		$this->assertFalse( has_filter( 'wp_generate_attachment_metadata' ) );
+		$this->assertFalse( has_filter( 'wp_insert_attachment_data' ) );
+		$this->assertNotFalse( has_filter( 'wp_get_attachment_url' ), 'Offloaded images are still served from Optimole.' );
+
+		$attachment_id = self::factory()->attachment->create_upload_object( OPTML_PATH . 'tests/assets/' . self::$files[0] . '.jpg' );
+		$meta          = wp_get_attachment_metadata( $attachment_id );
+
+		$this->assertFalse( Optml_Media_Offload::is_uploaded_image( $meta['file'] ) );
+		$this->assertFileExists( get_attached_file( $attachment_id ) );
+	}
+
 	public function test_retryable_error() {
 		Optml_Media_Offload::instance()->rollback_and_update_images([self::$sample_attachement]);
 		self::$error_mark = true;