diff --git a/src/browser/base/zen-components/ZenPinnedTabManager.mjs b/src/browser/base/zen-components/ZenPinnedTabManager.mjs
index 7c3544bec..18794d8e0 100644
--- a/src/browser/base/zen-components/ZenPinnedTabManager.mjs
+++ b/src/browser/base/zen-components/ZenPinnedTabManager.mjs
@@ -154,6 +154,10 @@
           newTab.setAttribute("zen-workspace-id", pin.workspaceUuid);
         }
 
+        if (pin.isEssential) {
+          newTab.setAttribute("zen-essential", "true");
+        }
+
         gBrowser.pinTab(newTab);
       }
 
@@ -178,10 +182,9 @@
             delete tab._zenClickEventListener;
           }
           break;
-          // TODO: Do this in a better way. Closing a second window could trigger remove tab and delete it from db
-        // case "TabClose":
-        //   this._removePinnedAttributes(tab);
-        //   break;
+        case "TabClose":
+          this._removePinnedAttributes(tab);
+          break;
         default:
           console.warn('ZenPinnedTabManager: Unhandled tab event', action);
           break;
@@ -189,8 +192,8 @@
     }
 
     _onTabClick(e) {
-      const tab = e.target;
-      if (e.button === 1) {
+      const tab = e.target?.closest("tab");
+      if (e.button === 1 && tab) {
         this._onCloseTabShortcut(e, tab);
       }
     }
@@ -222,10 +225,12 @@
         return;
       }
 
+      const userContextId = tab.getAttribute("usercontextid");
+
       pin.title = tab.label || browser.contentTitle;
       pin.url = browser.currentURI.spec;
       pin.workspaceUuid = tab.getAttribute("zen-workspace-id");
-      pin.userContextId = tab.getAttribute("userContextId");
+      pin.userContextId = userContextId ? parseInt(userContextId, 10) : 0;
 
       await ZenPinnedTabsStorage.savePin(pin);
       await this._refreshPinnedTabs();
@@ -240,13 +245,15 @@
       const browser = tab.linkedBrowser;
 
       const uuid = gZenUIManager.generateUuidv4();
+      const userContextId = tab.getAttribute("usercontextid");
 
       await ZenPinnedTabsStorage.savePin({
         uuid,
         title: tab.label || browser.contentTitle,
         url: browser.currentURI.spec,
-        containerTabId: tab.getAttribute("userContextId"),
-        workspaceUuid: tab.getAttribute("zen-workspace-id")
+        containerTabId: userContextId ? parseInt(userContextId, 10) : 0,
+        workspaceUuid: tab.getAttribute("zen-workspace-id"),
+        isEssential: tab.getAttribute("zen-essential") === "true"
       });
 
       tab.setAttribute("zen-pin-id", uuid);
@@ -369,6 +376,9 @@
       for (let i = 0; i < tabs.length; i++) {
         const tab = tabs[i];
         tab.setAttribute("zen-essential", "true");
+        if(tab.hasAttribute("zen-workspace-id")) {
+          tab.removeAttribute("zen-workspace-id");
+        }
         if (tab.pinned) {
           gBrowser.unpinTab(tab);
         }
@@ -381,6 +391,9 @@
       for (let i = 0; i < tabs.length; i++) {
         const tab = tabs[i];
         tab.removeAttribute("zen-essential");
+        if(ZenWorkspaces.workspaceEnabled && ZenWorkspaces.getActiveWorkspaceFromCache.uuid) {
+          tab.setAttribute("zen-workspace-id", ZenWorkspaces.getActiveWorkspaceFromCache.uuid);
+        }
         gBrowser.unpinTab(tab);
       }
     }
@@ -400,13 +413,17 @@
       document.getElementById('tabContextMenu').appendChild(elements);
 
       const element = window.MozXULElement.parseXULToFragment(`
-            <menuitem id="context_zen-pin-tab-global"
-                      data-lazy-l10n-id="tab-context-zen-pin-tab-global"
+            <menuitem id="context_zen-add-essential"
+                      data-lazy-l10n-id="tab-context-zen-add-essential"
                       hidden="true"
                       oncommand="gZenPinnedTabManager.addToEssentials();"/>
+            <menuitem id="context_zen-remove-essential"
+                      data-lazy-l10n-id="tab-context-zen-remove-essential"
+                      hidden="true"
+                      oncommand="gZenPinnedTabManager.removeEssentials();"/>
         `);
 
-      document.getElementById('context_pinTab').after(element);
+      document.getElementById('context_pinTab')?.after(element);
     }
 
     resetPinnedTabData(tabData) {
@@ -421,7 +438,10 @@
       const isVisible = contextTab.pinned  && !contextTab.multiselected;
       document.getElementById("context_zen-reset-pinned-tab").hidden = !isVisible || !contextTab.getAttribute("zen-pin-id");
       document.getElementById("context_zen-replace-pinned-url-with-current").hidden = !isVisible;
-      document.getElementById("context_zen-pin-tab-global").hidden = contextTab.pinned;
+      document.getElementById("context_zen-add-essential").hidden = contextTab.pinned;
+      document.getElementById("context_zen-remove-essential").hidden = !contextTab.getAttribute("zen-essential");
+      document.getElementById("context_unpinTab").hidden = document.getElementById("context_unpinTab").hidden || contextTab.getAttribute("zen-essential");
+      document.getElementById("context_unpinSelectedTabs").hidden = document.getElementById("context_unpinSelectedTabs").hidden || contextTab.getAttribute("zen-essential");
       document.getElementById("context_zen-pinned-tab-separator").hidden = !isVisible;
     }
   }
diff --git a/src/browser/themes/shared/zen-icons/essential-add.svg b/src/browser/themes/shared/zen-icons/essential-add.svg
new file mode 100644
index 000000000..fe1884096
--- /dev/null
+++ b/src/browser/themes/shared/zen-icons/essential-add.svg
@@ -0,0 +1 @@
+<?xml version="1.0" encoding="utf-8"?><svg version="1.1" xmlns="http://www.w3.org/2000/svg" x="0px" y="0px" viewBox="0 0 122.88 109.57" fill="context-fill" fill-opacity="context-fill-opacity" xml:space="preserve"><g><path d="M65.46,19.57c-0.68,0.72-1.36,1.45-2.2,2.32l-2.31,2.41l-2.4-2.33c-0.71-0.69-1.43-1.4-2.13-2.09 c-7.42-7.3-13.01-12.8-24.52-12.95c-0.45-0.01-0.93,0-1.43,0.02c-6.44,0.23-12.38,2.6-16.72,6.65c-4.28,4-7.01,9.67-7.1,16.57 c-0.01,0.43,0,0.88,0.02,1.37c0.69,19.27,19.13,36.08,34.42,50.01c2.95,2.69,5.78,5.27,8.49,7.88l11.26,10.85l14.15-14.04 c2.28-2.26,4.86-4.73,7.62-7.37c4.69-4.5,9.91-9.49,14.77-14.52c3.49-3.61,6.8-7.24,9.61-10.73c2.76-3.42,5.02-6.67,6.47-9.57 c2.38-4.76,3.13-9.52,2.62-13.97c-0.5-4.39-2.23-8.49-4.82-11.99c-2.63-3.55-6.13-6.49-10.14-8.5C96.5,7.29,91.21,6.2,85.8,6.82 C76.47,7.9,71.5,13.17,65.46,19.57L65.46,19.57z M60.77,14.85C67.67,7.54,73.4,1.55,85.04,0.22c6.72-0.77,13.3,0.57,19.03,3.45 c4.95,2.48,9.27,6.1,12.51,10.47c3.27,4.42,5.46,9.61,6.1,15.19c0.65,5.66-0.29,11.69-3.3,17.69c-1.7,3.39-4.22,7.03-7.23,10.76 c-2.95,3.66-6.39,7.44-10,11.17C97.2,74.08,91.94,79.12,87.2,83.66c-2.77,2.65-5.36,5.13-7.54,7.29L63.2,107.28l-2.31,2.29 l-2.34-2.25l-13.6-13.1c-2.49-2.39-5.37-5.02-8.36-7.75C20.38,71.68,0.81,53.85,0.02,31.77C0,31.23,0,30.67,0,30.09 c0.12-8.86,3.66-16.18,9.21-21.36c5.5-5.13,12.97-8.13,21.01-8.42c0.55-0.02,1.13-0.03,1.74-0.02C46,0.48,52.42,6.63,60.77,14.85 L60.77,14.85z"/></g></svg>
\ No newline at end of file
diff --git a/src/browser/themes/shared/zen-icons/essential-remove.svg b/src/browser/themes/shared/zen-icons/essential-remove.svg
new file mode 100644
index 000000000..5cd39c9b9
--- /dev/null
+++ b/src/browser/themes/shared/zen-icons/essential-remove.svg
@@ -0,0 +1 @@
+<svg data-name="Layer 1" xmlns="http://www.w3.org/2000/svg" viewBox="0 0 122.88 109.57" fill="context-fill" fill-opacity="context-fill-opacity"><defs><style>.cls-1{fill-rule:evenodd;}</style></defs><path class="cls-1" d="M94.26,44.46A26.88,26.88,0,1,1,67.38,71.34,26.88,26.88,0,0,1,94.26,44.46ZM65.45,19.57l-4.52,4.74-4.52-4.43C49,12.58,43.4,7.08,31.89,6.93L30.46,7A25.75,25.75,0,0,0,13.74,13.6,22.58,22.58,0,0,0,6.63,30.17l0,1.37c.69,19.27,19.13,36.08,34.42,50,3,2.69,5.78,5.27,8.49,7.88l11.27,10.85,5.91-5.87c.68.8,1.39,1.58,2.13,2.32l0,0c.82.83,1.69,1.61,2.59,2.36l-10.59,10.5L45,94.22c-2.49-2.39-5.37-5-8.37-7.75C20.37,71.68.81,53.85,0,31.77l0-1.68A29.12,29.12,0,0,1,9.21,8.73a32.42,32.42,0,0,1,21-8.42H32c14,.18,20.45,6.34,28.8,14.55C67.66,7.54,73.39,1.55,85,.21a33.88,33.88,0,0,1,19,3.45,35.14,35.14,0,0,1,12.51,10.48,31.53,31.53,0,0,1,6.1,15.18,31,31,0,0,1-2.86,16.81l-.17-.18a36.18,36.18,0,0,0-5.14-4.27,24.26,24.26,0,0,0,1.57-11.6,25,25,0,0,0-4.83-12,28.62,28.62,0,0,0-10.14-8.5A27.27,27.27,0,0,0,85.79,6.82C76.47,7.89,71.5,13.17,65.45,19.57ZM106.15,68a4,4,0,0,1,1.51.3,3.94,3.94,0,0,1,1.29.86,4,4,0,0,1,.85,1.28l0,.06a4,4,0,0,1,.28,1.38V72a3.82,3.82,0,0,1-.3,1.44,4,4,0,0,1-.86,1.29,3.88,3.88,0,0,1-1.27.85l-.07,0a4.23,4.23,0,0,1-1.43.28H82.37a3.85,3.85,0,0,1-1.51-.31l-.06,0a3.92,3.92,0,0,1-1.23-.83,3.87,3.87,0,0,1-.85-1.28l0-.07A4.23,4.23,0,0,1,78.41,72v0a3.8,3.8,0,0,1,.3-1.51A3.95,3.95,0,0,1,82.34,68Z"/></svg>
\ No newline at end of file
diff --git a/src/browser/themes/shared/zen-icons/icons.css b/src/browser/themes/shared/zen-icons/icons.css
index c59bd5ef5..a78485e28 100644
--- a/src/browser/themes/shared/zen-icons/icons.css
+++ b/src/browser/themes/shared/zen-icons/icons.css
@@ -893,11 +893,18 @@ menuitem[contexttype='fullscreen'][label*='Exit'] {
 #context_pinSelectedTabs,
 #context_unpinSelectedTabs,
 .customize-context-moveToPanel,
-#context_zen-replace-pinned-url-with-current,
-#context_zen-pin-tab-global{
+#context_zen-replace-pinned-url-with-current{
   --menu-image: url('pin.svg');
 }
 
+#context_zen-add-essential {
+  --menu-image: url('essential-add.svg');
+}
+
+#context_zen-remove-essential {
+  --menu-image: url('essential-remove.svg');
+}
+
 .customize-context-removeFromToolbar {
   --menu-image: url('unpin.svg');
 }