diff --git a/apps/macos/Sources/Clawdis/MenuBar.swift b/apps/macos/Sources/Clawdis/MenuBar.swift
index 373082b1f..19eb30b6e 100644
--- a/apps/macos/Sources/Clawdis/MenuBar.swift
+++ b/apps/macos/Sources/Clawdis/MenuBar.swift
@@ -14,6 +14,7 @@ struct ClawdisApp: App {
     @StateObject private var activityStore = WorkActivityStore.shared
     @State private var statusItem: NSStatusItem?
     @State private var isMenuPresented = false
+    private let menuDelegate = StatusMenuDelegate()
 
     init() {
         _state = StateObject(wrappedValue: AppStateStore.shared)
@@ -36,6 +37,7 @@ struct ClawdisApp: App {
             self.statusItem = item
             self.applyStatusItemAppearance(paused: self.state.isPaused)
             self.installStatusItemMouseHandler(for: item)
+            self.attachMenuDelegate(to: item)
         }
         .onChange(of: self.state.isPaused) { _, paused in
             self.applyStatusItemAppearance(paused: paused)
@@ -63,6 +65,8 @@ struct ClawdisApp: App {
             self.statusItem?.button?.highlight(visible)
         }
 
+        self.menuDelegate.button = button
+
         let handler = StatusItemMouseHandlerView()
         handler.translatesAutoresizingMaskIntoConstraints = false
         handler.onLeftClick = { [self] in self.toggleWebChatPanel() }
@@ -77,6 +81,13 @@ struct ClawdisApp: App {
         ])
     }
 
+    @MainActor
+    private func attachMenuDelegate(to item: NSStatusItem) {
+        guard let menu = item.menu else { return }
+        self.menuDelegate.button = item.button
+        menu.delegate = self.menuDelegate
+    }
+
     @MainActor
     private func toggleWebChatPanel() {
         guard AppStateStore.webChatEnabled else {
@@ -130,6 +141,18 @@ private final class StatusItemMouseHandlerView: NSView {
     }
 }
 
+private final class StatusMenuDelegate: NSObject, NSMenuDelegate {
+    weak var button: NSStatusBarButton?
+
+    func menuWillOpen(_ menu: NSMenu) {
+        self.button?.highlight(true)
+    }
+
+    func menuDidClose(_ menu: NSMenu) {
+        self.button?.highlight(false)
+    }
+}
+
 final class AppDelegate: NSObject, NSApplicationDelegate, NSXPCListenerDelegate {
     private var listener: NSXPCListener?
     private var state: AppState?