diff --git a/projects/plugins/jetpack/changelog/jetpack-1757-widget-visibility-gutenberg b/projects/plugins/jetpack/changelog/jetpack-1757-widget-visibility-gutenberg
new file mode 100644
index 000000000000..eae2a8704b4e
--- /dev/null
+++ b/projects/plugins/jetpack/changelog/jetpack-1757-widget-visibility-gutenberg
@@ -0,0 +1,4 @@
+Significance: patch
+Type: bugfix
+
+Widget Visibility: restore visibility controls for legacy widgets in the block-based widget editor.
diff --git a/projects/plugins/jetpack/modules/widget-visibility/widget-conditions.php b/projects/plugins/jetpack/modules/widget-visibility/widget-conditions.php
index 40959a84b621..650ae37ff7bb 100644
--- a/projects/plugins/jetpack/modules/widget-visibility/widget-conditions.php
+++ b/projects/plugins/jetpack/modules/widget-visibility/widget-conditions.php
@@ -117,7 +117,14 @@ public static function init() {
 		}
 
 		if ( $add_data_assets_to_page ) {
-			add_action( 'sidebar_admin_setup', array( __CLASS__, 'widget_admin_setup' ) );
+			// In the classic widget editor, sidebar_admin_setup fires and is the correct hook.
+			// In the Gutenberg block widget editor, sidebar_admin_setup may not fire, so we
+			// also register on enqueue_block_editor_assets to ensure assets are always loaded.
+			if ( $using_classic_experience ) {
+				add_action( 'sidebar_admin_setup', array( __CLASS__, 'widget_admin_setup' ) );
+			} else {
+				add_action( 'enqueue_block_editor_assets', array( __CLASS__, 'widget_admin_setup' ) );
+			}
 		}
 
 		if ( $add_block_controls ) {
@@ -203,7 +210,10 @@ public static function add_block_attributes_filter() {
 	 * Prepare the interface for editing widgets - loading css, javascript & data
 	 */
 	public static function widget_admin_setup() {
-		wp_enqueue_style( 'widget-conditions', plugins_url( 'widget-conditions/widget-conditions.css', __FILE__ ), array( 'widgets' ), JETPACK__VERSION );
+		// The 'widgets' style handle is only registered in the classic widget editor.
+		// In the Gutenberg block widget editor it is absent, so omit it as a dependency.
+		$style_deps = wp_use_widgets_block_editor() ? array() : array( 'widgets' );
+		wp_enqueue_style( 'widget-conditions', plugins_url( 'widget-conditions/widget-conditions.css', __FILE__ ), $style_deps, JETPACK__VERSION );
 		wp_style_add_data( 'widget-conditions', 'rtl', 'replace' );
 		wp_enqueue_script(
 			'widget-conditions',
diff --git a/projects/plugins/jetpack/modules/widget-visibility/widget-conditions/widget-conditions.js b/projects/plugins/jetpack/modules/widget-visibility/widget-conditions/widget-conditions.js
index bf3e51f65e31..7de13f794e6d 100644
--- a/projects/plugins/jetpack/modules/widget-visibility/widget-conditions/widget-conditions.js
+++ b/projects/plugins/jetpack/modules/widget-visibility/widget-conditions/widget-conditions.js
@@ -112,7 +112,7 @@ jQuery( function ( $ ) {
 
 	widgets_shell.on( 'click.widgetconditions', 'a.display-options', function ( e ) {
 		var $displayOptionsButton = $( this ),
-			$widget = $displayOptionsButton.closest( 'div.widget' );
+			$widget = $displayOptionsButton.closest( 'div.widget, .wp-block-legacy-widget__edit-form' );
 
 		e.preventDefault();
 
@@ -137,7 +137,10 @@ jQuery( function ( $ ) {
 		e.preventDefault();
 
 		if ( $condition.is( ':first-child' ) && $condition.is( ':last-child' ) ) {
-			$( this ).closest( 'div.widget' ).find( 'a.display-options' ).click();
+			$( this )
+				.closest( 'div.widget, .wp-block-legacy-widget__edit-form' )
+				.find( 'a.display-options' )
+				.click();
 			$condition.find( 'select.conditions-rule-major' ).val( '' ).change();
 		} else {
 			$condition.find( 'select.conditions-rule-major' ).change();