diff --git a/projects/plugins/jetpack/changelog/wpcom-admin-menu-bypass-special-cases b/projects/plugins/jetpack/changelog/wpcom-admin-menu-bypass-special-cases
new file mode 100644
index 0000000000000..cd059c24184ef
--- /dev/null
+++ b/projects/plugins/jetpack/changelog/wpcom-admin-menu-bypass-special-cases
@@ -0,0 +1,4 @@
+Significance: patch
+Type: other
+
+WPCOM: Admin Menu customizations bypassed on files that do not render a menu
diff --git a/projects/plugins/jetpack/modules/masterbar/admin-menu/load.php b/projects/plugins/jetpack/modules/masterbar/admin-menu/load.php
index 412819effd2ef..ea1a54a9795eb 100644
--- a/projects/plugins/jetpack/modules/masterbar/admin-menu/load.php
+++ b/projects/plugins/jetpack/modules/masterbar/admin-menu/load.php
@@ -35,6 +35,21 @@ function should_customize_nav( $admin_menu_class ) {
 		return false;
 	}
 
+	// WPCOM-specific exemptions.
+	if ( is_a( $admin_menu_class, WPcom_Admin_Menu::class, true ) && ! $is_api_request ) {
+		$script_filename = ( ! empty( $_SERVER['SCRIPT_FILENAME'] ) ) ? basename( $_SERVER['SCRIPT_FILENAME'] ) : null;
+
+		// Special case: /wp-admin/?service-worker doesn't render a menu at all: skip all menu work.
+		if ( 'index.php' === $script_filename && isset( $_GET['service-worker'] ) ) { // phpcs:ignore WordPress.Security.NonceVerification.Recommended
+			return false;
+		}
+
+		// Special case: index-yourstuff.php and index-hotstuff.php don't render menus.
+		if ( 'index-yourstuff.php' === $script_filename || 'index-hotstuff.php' === $script_filename ) {
+			return false;
+		}
+	}
+
 	return true;
 }