diff --git a/src/browser/base/content/ZenStartup.mjs b/src/browser/base/content/ZenStartup.mjs
index 3c8cffb21..f8b5c4671 100644
--- a/src/browser/base/content/ZenStartup.mjs
+++ b/src/browser/base/content/ZenStartup.mjs
@@ -33,7 +33,6 @@
         ZenWorkspaces.init();
         gZenVerticalTabsManager.init();
         gZenUIManager.init();
-        gZenCompactModeManager.init();
 
         this._checkForWelcomePage();
 
@@ -42,6 +41,7 @@
         console.error('ZenThemeModifier: Error initializing browser layout', e);
       }
       ZenWorkspaces.promiseInitialized.then(() => {
+        gZenCompactModeManager.init();
         this.closeWatermark();
       });
     },
diff --git a/src/browser/base/zen-components/ZenCompactMode.mjs b/src/browser/base/zen-components/ZenCompactMode.mjs
index fa26ae112..cff31df2f 100644
--- a/src/browser/base/zen-components/ZenCompactMode.mjs
+++ b/src/browser/base/zen-components/ZenCompactMode.mjs
@@ -166,6 +166,7 @@ var gZenCompactModeManager = {
       await this.animateCompactMode();
       this._evenListeners.forEach((callback) => callback());
     }
+    gZenUIManager.updateTabsToolbar();
   },
 
   // NOTE: Dont actually use event, it's just so we make sure