diff --git a/src/browser/app/profile/zen-browser.js b/src/browser/app/profile/zen-browser.js
index e0d21b352..fb124d615 100644
--- a/src/browser/app/profile/zen-browser.js
+++ b/src/browser/app/profile/zen-browser.js
@@ -143,6 +143,7 @@ pref('zen.view.sidebar-expanded.max-width', 500);
 
 #ifdef XP_MACOSX
 pref('zen.view.mac.show-three-dot-menu', false);
+pref('zen.widget.mac.mono-window-controls', true);
 #endif
 pref('zen.view.show-bottom-border', false);
 pref('zen.view.use-single-toolbar', true);
diff --git a/src/browser/base/content/zen-styles/zen-browser-ui.css b/src/browser/base/content/zen-styles/zen-browser-ui.css
index 0257ac92f..92f956bea 100644
--- a/src/browser/base/content/zen-styles/zen-browser-ui.css
+++ b/src/browser/base/content/zen-styles/zen-browser-ui.css
@@ -152,12 +152,32 @@
   gap: var(--zen-element-separation);
 }
 
-.titlebar-buttonbox-container {
-  height: 100%;
+@media not (-moz-platform: macos) { 
+  .titlebar-buttonbox-container {
+    height: 100%;
+  }
 }
 
 @media (-moz-platform: macos) {
   .titlebar-buttonbox-container {
     margin-inline-end: 8px;
+
+    & > .titlebar-buttonbox {
+      margin-inline-start: var(--zen-toolbox-padding);
+    }
+  }
+
+  @media (-moz-bool-pref: 'zen.widget.mac.mono-window-controls') {
+    .titlebar-buttonbox-container {
+      /* Draw 3 dots as background to represent the window controls,
+        all with the same cololr as the titlebar */
+      background-image: radial-gradient(circle, #4d4c4a 6px, transparent 0.5px);
+      background-size: 20px 22px;
+      background-position: 52% 50%;
+
+      &:not([zen-has-hover='true']) > .titlebar-buttonbox {
+        opacity: 0;
+      }
+    }
   }
 }
diff --git a/src/browser/base/zen-components/ZenCompactMode.mjs b/src/browser/base/zen-components/ZenCompactMode.mjs
index 56bf32ecb..d510aed56 100644
--- a/src/browser/base/zen-components/ZenCompactMode.mjs
+++ b/src/browser/base/zen-components/ZenCompactMode.mjs
@@ -292,6 +292,9 @@ var gZenCompactModeManager = {
         element: document.getElementById('zen-appcontent-navbar-container'),
         screenEdge: 'top',
       },
+      {
+        element: gZenVerticalTabsManager.actualWindowButtons,
+      }
     ];
   },
 
@@ -336,8 +339,9 @@ var gZenCompactModeManager = {
       target.addEventListener('mouseleave', (event) => {
         // If on Mac, ignore mouseleave in the area of window buttons
         if (AppConstants.platform == 'macosx') {
-          const MAC_WINDOW_BUTTONS_X_BORDER = 75;
-          const MAC_WINDOW_BUTTONS_Y_BORDER = 40;
+          const buttonRect = gZenVerticalTabsManager.actualWindowButtons.getBoundingClientRect();
+          const MAC_WINDOW_BUTTONS_X_BORDER = buttonRect.width + buttonRect.x;
+          const MAC_WINDOW_BUTTONS_Y_BORDER = buttonRect.height + buttonRect.y;
           if (event.clientX < MAC_WINDOW_BUTTONS_X_BORDER && event.clientY < MAC_WINDOW_BUTTONS_Y_BORDER) {
             return;
           }
diff --git a/src/modules/libpref/init/StaticPrefList-yaml.patch b/src/modules/libpref/init/StaticPrefList-yaml.patch
index fadcff2b1..ac8018292 100644
--- a/src/modules/libpref/init/StaticPrefList-yaml.patch
+++ b/src/modules/libpref/init/StaticPrefList-yaml.patch
@@ -1,8 +1,8 @@
 diff --git a/modules/libpref/init/StaticPrefList.yaml b/modules/libpref/init/StaticPrefList.yaml
-index 7364514f74703184462e8dbce3f0aafc3f850a3d..560671beddf6c216e918a47bd5dbd4e770a24ec7 100644
+index ce2393978f77f55f42ae9b97e5d40328ce8eaae4..a426679de76c2d172974ec87f5fe48e22d5ab7b0 100644
 --- a/modules/libpref/init/StaticPrefList.yaml
 +++ b/modules/libpref/init/StaticPrefList.yaml
-@@ -18067,7 +18067,7 @@
+@@ -18060,7 +18060,7 @@
  # Whether we use the mica backdrop. Off by default for now.
  - name: widget.windows.mica
    type: bool
@@ -11,7 +11,7 @@ index 7364514f74703184462e8dbce3f0aafc3f850a3d..560671beddf6c216e918a47bd5dbd4e7
    mirror: once
  #endif
  
-@@ -18180,6 +18180,26 @@
+@@ -18173,6 +18173,19 @@
    mirror: always
  #endif
  
@@ -21,13 +21,6 @@ index 7364514f74703184462e8dbce3f0aafc3f850a3d..560671beddf6c216e918a47bd5dbd4e7
 +  value: true
 +  mirror: never
 +
-+#ifdef XP_MACOSX
-+- name: zen.widget.mac.mono-window-controls
-+  type: RelaxedAtomicBool
-+  value: false
-+  mirror: always
-+#endif
-+
 +#ifdef XP_WIN
 +- name: zen.widget.windows.acrylic
 +  type: bool
diff --git a/src/widget/cocoa/nsCocoaWindow-mm.patch b/src/widget/cocoa/nsCocoaWindow-mm.patch
deleted file mode 100644
index 071a19813..000000000
--- a/src/widget/cocoa/nsCocoaWindow-mm.patch
+++ /dev/null
@@ -1,27 +0,0 @@
-diff --git a/widget/cocoa/nsCocoaWindow.mm b/widget/cocoa/nsCocoaWindow.mm
-index f1c87dd8faef8c6caf9248ce7d9f40c12f5db9f6..f5280b8fc6cf46d3941d1ff04835b12dd2755170 100644
---- a/widget/cocoa/nsCocoaWindow.mm
-+++ b/widget/cocoa/nsCocoaWindow.mm
-@@ -51,6 +51,7 @@
- #include "mozilla/ScopeExit.h"
- #include "mozilla/StaticPrefs_gfx.h"
- #include "mozilla/StaticPrefs_widget.h"
-+#include "mozilla/StaticPrefs_zen.h"
- #include "mozilla/WritingModes.h"
- #include "mozilla/layers/CompositorBridgeChild.h"
- #include "mozilla/widget/Screen.h"
-@@ -682,9 +683,11 @@ static unsigned int WindowMaskForBorderStyle(BorderStyle aBorderStyle) {
-       continue;
-     }
-     NSWindow* win = ancestor->GetCocoaWindow();
--    [[win standardWindowButton:NSWindowCloseButton] setEnabled:!aModal];
--    [[win standardWindowButton:NSWindowMiniaturizeButton] setEnabled:!aModal];
--    [[win standardWindowButton:NSWindowZoomButton] setEnabled:!aModal];
-+
-+    auto zenBtnEnabled = StaticPrefs::zen_widget_mac_mono_window_controls() ? false : !aModal;
-+    [[win standardWindowButton:NSWindowCloseButton] setEnabled:zenBtnEnabled];
-+    [[win standardWindowButton:NSWindowMiniaturizeButton] setEnabled:zenBtnEnabled];
-+    [[win standardWindowButton:NSWindowZoomButton] setEnabled:zenBtnEnabled];
-   }
-   if (aModal) {
-     mWindow.level = NSModalPanelWindowLevel;