diff --git a/src/browser/base/content/ZenUIManager.mjs b/src/browser/base/content/ZenUIManager.mjs
index 40d87ef70..5fcb5702a 100644
--- a/src/browser/base/content/ZenUIManager.mjs
+++ b/src/browser/base/content/ZenUIManager.mjs
@@ -133,6 +133,8 @@ var gZenCompactModeManager = {
   init() {
     Services.prefs.addObserver('zen.view.compact', this._updateEvent.bind(this));
     Services.prefs.addObserver('zen.view.compact.toolbar-flash-popup.duration', this._updatedSidebarFlashDuration.bind(this));
+
+    this.sidebar.addEventListener('contextmenu', this.keepSidebarVisibleOnContextMenu.bind(this));
   },
 
   get prefefence() {
@@ -143,6 +145,13 @@ var gZenCompactModeManager = {
     Services.prefs.setBoolPref('zen.view.compact', value);
   },
 
+  get sidebar() {
+    if (!this._sidebar) {
+      this._sidebar= document.getElementById('navigator-toolbox');
+    }
+    return this._sidebar;
+  },
+
   _updateEvent() {
     Services.prefs.setBoolPref('zen.view.sidebar-expanded.on-hover', false);
   },
@@ -156,8 +165,7 @@ var gZenCompactModeManager = {
   },
 
   toggleSidebar() {
-    let sidebar = document.getElementById('navigator-toolbox');
-    sidebar.toggleAttribute('zen-user-show');
+    this.sidebar.toggleAttribute('zen-user-show');
   },
 
   get flashSidebarDuration() {
@@ -168,24 +176,48 @@ var gZenCompactModeManager = {
   },
 
   flashSidebar() {
-    let sidebar = document.getElementById('navigator-toolbox');
     let tabPanels = document.getElementById('tabbrowser-tabpanels');
-    if (sidebar.matches(':hover') || tabPanels.matches("[zen-split-view='true']")) {
+    if (this.sidebar.matches(':hover') || tabPanels.matches("[zen-split-view='true']")) {
       return;
     }
     if (this._flashSidebarTimeout) {
       clearTimeout(this._flashSidebarTimeout);
     } else {
-      window.requestAnimationFrame(() => sidebar.setAttribute('flash-popup', ''));
+      window.requestAnimationFrame(() => this.sidebar.setAttribute('flash-popup', ''));
     }
     this._flashSidebarTimeout = setTimeout(() => {
       window.requestAnimationFrame(() => {
-        sidebar.removeAttribute('flash-popup');
+        this.sidebar.removeAttribute('flash-popup');
         this._flashSidebarTimeout = null;
       });
     }, this.flashSidebarDuration);
   },
 
+  keepSidebarVisibleOnContextMenu() {
+    this.sidebar.setAttribute('has-popup-menu', '');
+    /* If the cursor is on the popup when it hides, the :hover effect will not be reapplied to the sidebar until the cursor moves,
+     to mitigate this: Check if the mouse is on the sidebar when popup removed, wait until mousemove to remove the has-popup-menu attribute.
+     */
+    if (!this.__removeHasPopupAttribute) {
+      this.__removeHasPopupAttribute = () => this.sidebar.removeAttribute('has-popup-menu');
+    }
+    removeEventListener('mousemove', this.__removeHasPopupAttribute);
+
+    let lastMouseEvent;
+    const trackMouse = (event) => lastMouseEvent = event;
+    addEventListener('mousemove', trackMouse);
+    addEventListener('popuphidden', () => {
+      removeEventListener('mousemove', trackMouse);
+      const rect = this.sidebar.getBoundingClientRect();
+      if (rect.left < lastMouseEvent.screenX && lastMouseEvent.screenX < rect.right
+        && rect.top < lastMouseEvent.screenY && lastMouseEvent.screenY < rect.bottom) {
+        addEventListener('mousemove', this.__removeHasPopupAttribute, {once: true});
+      } else {
+        this.__removeHasPopupAttribute();
+      }
+    }, {once: true});
+  },
+
   toggleToolbar() {
     let toolbar = document.getElementById('zen-appcontent-navbar-container');
     toolbar.toggleAttribute('zen-user-show');
diff --git a/src/browser/base/content/zen-styles/zen-compact-mode.css b/src/browser/base/content/zen-styles/zen-compact-mode.css
index eda76c8a4..1f0e34bff 100644
--- a/src/browser/base/content/zen-styles/zen-compact-mode.css
+++ b/src/browser/base/content/zen-styles/zen-compact-mode.css
@@ -14,8 +14,8 @@
 
   #navigator-toolbox {
     --zen-compact-toolbox-margin-single: calc(var(--zen-element-separation) * 2);
-    --zen-compact-toolbox-margin: 
-      calc(var(--zen-compact-toolbox-margin-single) / 2) var(--zen-compact-toolbox-margin-single) 
+    --zen-compact-toolbox-margin:
+      calc(var(--zen-compact-toolbox-margin-single) / 2) var(--zen-compact-toolbox-margin-single)
       calc(var(--zen-compact-toolbox-margin-single) + var(--zen-element-separation)) var(--zen-compact-toolbox-margin-single);
     position: absolute !important;
     display: block;
@@ -92,9 +92,9 @@
        *  3. Add element separation variable, to avoid overlaping with the toolbar
        *  4. Calculate toolbar height, taken from zen-urlbar.css
        */
-      --zen-compact-toolbox-margin: calc( 
-        var(--zen-element-separation) + 0.8rem + 
-        (18px + (var(--toolbarbutton-inner-padding) * 2)) 
+      --zen-compact-toolbox-margin: calc(
+        var(--zen-element-separation) + 0.8rem +
+        (18px + (var(--toolbarbutton-inner-padding) * 2))
       ) var(--zen-compact-toolbox-margin-single) var(--zen-compact-toolbox-margin-single) var(--zen-compact-toolbox-margin-single);
 
       margin-top: 0 !important;
@@ -120,6 +120,7 @@
   #navigator-toolbox:focus-within,
   #navigator-toolbox[zen-user-show],
   #navigator-toolbox[flash-popup],
+  #navigator-toolbox[has-popup-menu],
   #navigator-toolbox[movingtab],
   #mainPopupSet:has(> #appMenu-popup:hover) ~ toolbox,
   #navigator-toolbox:has(.tabbrowser-tab:active),