diff --git a/css/leptonChrome.css b/css/leptonChrome.css
index 674f300..8528b9a 100644
--- a/css/leptonChrome.css
+++ b/css/leptonChrome.css
@@ -11806,7 +11806,8 @@
         #context-sendpagetodevice-popup,
         #context-sendlinktodevice-popup,
         #frame > menupopup,
-        #spell-dictionaries-menu
+        #spell-dictionaries-menu,
+        #context-ask-chat > menupopup
       )
       > menuitem:not([type="checkbox"][checked="true"], [type="radio"]),
     .openintabs-menuitem,
@@ -11891,7 +11892,8 @@
         #context-sendpagetodevice-popup,
         #context-sendlinktodevice-popup,
         #frame > menupopup,
-        #spell-dictionaries-menu
+        #spell-dictionaries-menu,
+        #context-ask-chat > menupopup
       )
       > menuitem:not([type="checkbox"][checked="true"], [type="radio"]),
     .openintabs-menuitem,
@@ -11985,7 +11987,8 @@
           #context-sendpagetodevice-popup,
           #context-sendlinktodevice-popup,
           #frame > menupopup,
-          #spell-dictionaries-menu
+          #spell-dictionaries-menu,
+          #context-ask-chat > menupopup
         )
         > menuitem:not([type="checkbox"][checked="true"], [type="radio"]),
       .openintabs-menuitem,
@@ -12054,7 +12057,8 @@
               #context-sendpagetodevice-popup,
               #context-sendlinktodevice-popup,
               #frame > menupopup,
-              #spell-dictionaries-menu
+              #spell-dictionaries-menu,
+              #context-ask-chat > menupopup
             )
             > menuitem:not([type="checkbox"][checked="true"], [type="radio"]),
           .openintabs-menuitem,
@@ -12803,6 +12807,35 @@
           --menuitem-image: url("chrome://browser/skin/bookmark.svg");
         }
       }
+      /*= context-ask-chat =========================================================*/
+      #ask-chat-shortcuts .toolbarbutton-icon {
+        order: -1;
+        margin-inline-end: var(--arrowpanel-menuitem-margin-inline) !important;
+      }
+      #ask-chat-shortcuts .subviewbutton:nth-child(1) {
+        list-style-image: url("../icons/apps-list-detail.svg");
+      }
+      #ask-chat-shortcuts .subviewbutton:nth-child(2) {
+        list-style-image: url("../icons/code-text.svg");
+      }
+      #ask-chat-shortcuts .subviewbutton:nth-child(3) {
+        list-style-image: url("../icons/tetris-app.svg");
+      }
+      #ask-chat-shortcuts .subviewbutton:nth-child(4) {
+        list-style-image: url("../icons/arrow-up-exclamation.svg");
+      }
+      #context-ask-chat menuitem:nth-child(1) {
+        --menuitem-image: url("../icons/apps-list-detail.svg");
+      }
+      #context-ask-chat menuitem:nth-child(2) {
+        --menuitem-image: url("../icons/code-text.svg");
+      }
+      #context-ask-chat menuitem:nth-child(3) {
+        --menuitem-image: url("../icons/tetris-app.svg");
+      }
+      #context-ask-chat menuitem:nth-child(4) {
+        --menuitem-image: url("../icons/arrow-up-exclamation.svg");
+      }
       /*= main-context-menu-frame ==================================================*/
       #context-showonlythisframe {
         --menuitem-image: url("../icons/eye-show.svg");
@@ -26895,7 +26928,8 @@
       #context-sendpagetodevice-popup,
       #context-sendlinktodevice-popup,
       #frame > menupopup,
-      #spell-dictionaries-menu
+      #spell-dictionaries-menu,
+      #context-ask-chat > menupopup
     )
     > menuitem:not([type="checkbox"][checked="true"], [type="radio"]),
   .openintabs-menuitem,
@@ -26999,7 +27033,8 @@
       #context-sendpagetodevice-popup,
       #context-sendlinktodevice-popup,
       #frame > menupopup,
-      #spell-dictionaries-menu
+      #spell-dictionaries-menu,
+      #context-ask-chat > menupopup
     )
     > menuitem:not([type="checkbox"][checked="true"], [type="radio"]),
   .openintabs-menuitem,
@@ -27092,7 +27127,8 @@
       #context-sendpagetodevice-popup,
       #context-sendlinktodevice-popup,
       #frame > menupopup,
-      #spell-dictionaries-menu
+      #spell-dictionaries-menu,
+      #context-ask-chat > menupopup
     )
     > menuitem:not([type="checkbox"][checked="true"], [type="radio"]),
   .openintabs-menuitem,
@@ -27156,7 +27192,8 @@
       #context-sendpagetodevice-popup,
       #context-sendlinktodevice-popup,
       #frame > menupopup,
-      #spell-dictionaries-menu
+      #spell-dictionaries-menu,
+      #context-ask-chat > menupopup
     )
     > menuitem:not([type="checkbox"][checked="true"], [type="radio"]),
   .openintabs-menuitem,
@@ -27458,6 +27495,7 @@
   /*= toolbar-context-menu =====================================================*/
   /*= Tab Mix Plus =============================================================*/
   /*= contentAreaContextMenu ===================================================*/
+  /*= context-ask-chat =========================================================*/
   /*= main-context-menu-frame ==================================================*/
   /*= Tab Mix Plus =============================================================*/
   /*= downloadsContextMenu =====================================================*/ /*= placeContext =============================================================*/ /*= Notification =============================================================*/
@@ -28130,6 +28168,52 @@
     --menuitem-image: url("chrome://browser/skin/bookmark.svg");
   }
 }
+@media (not (-moz-bool-pref: "userChrome.icon.disabled")) and (-moz-bool-pref: "userChrome.icon.menu") and (-moz-bool-pref: "userChrome.icon.context_menu") {
+  #ask-chat-shortcuts .toolbarbutton-icon {
+    order: -1;
+    margin-inline-end: var(--arrowpanel-menuitem-margin-inline) !important;
+  }
+}
+@media (not (-moz-bool-pref: "userChrome.icon.disabled")) and (-moz-bool-pref: "userChrome.icon.menu") and (-moz-bool-pref: "userChrome.icon.context_menu") {
+  #ask-chat-shortcuts .subviewbutton:nth-child(1) {
+    list-style-image: url("../icons/apps-list-detail.svg");
+  }
+}
+@media (not (-moz-bool-pref: "userChrome.icon.disabled")) and (-moz-bool-pref: "userChrome.icon.menu") and (-moz-bool-pref: "userChrome.icon.context_menu") {
+  #ask-chat-shortcuts .subviewbutton:nth-child(2) {
+    list-style-image: url("../icons/code-text.svg");
+  }
+}
+@media (not (-moz-bool-pref: "userChrome.icon.disabled")) and (-moz-bool-pref: "userChrome.icon.menu") and (-moz-bool-pref: "userChrome.icon.context_menu") {
+  #ask-chat-shortcuts .subviewbutton:nth-child(3) {
+    list-style-image: url("../icons/tetris-app.svg");
+  }
+}
+@media (not (-moz-bool-pref: "userChrome.icon.disabled")) and (-moz-bool-pref: "userChrome.icon.menu") and (-moz-bool-pref: "userChrome.icon.context_menu") {
+  #ask-chat-shortcuts .subviewbutton:nth-child(4) {
+    list-style-image: url("../icons/arrow-up-exclamation.svg");
+  }
+}
+@media (not (-moz-bool-pref: "userChrome.icon.disabled")) and (-moz-bool-pref: "userChrome.icon.menu") and (-moz-bool-pref: "userChrome.icon.context_menu") {
+  #context-ask-chat menuitem:nth-child(1) {
+    --menuitem-image: url("../icons/apps-list-detail.svg");
+  }
+}
+@media (not (-moz-bool-pref: "userChrome.icon.disabled")) and (-moz-bool-pref: "userChrome.icon.menu") and (-moz-bool-pref: "userChrome.icon.context_menu") {
+  #context-ask-chat menuitem:nth-child(2) {
+    --menuitem-image: url("../icons/code-text.svg");
+  }
+}
+@media (not (-moz-bool-pref: "userChrome.icon.disabled")) and (-moz-bool-pref: "userChrome.icon.menu") and (-moz-bool-pref: "userChrome.icon.context_menu") {
+  #context-ask-chat menuitem:nth-child(3) {
+    --menuitem-image: url("../icons/tetris-app.svg");
+  }
+}
+@media (not (-moz-bool-pref: "userChrome.icon.disabled")) and (-moz-bool-pref: "userChrome.icon.menu") and (-moz-bool-pref: "userChrome.icon.context_menu") {
+  #context-ask-chat menuitem:nth-child(4) {
+    --menuitem-image: url("../icons/arrow-up-exclamation.svg");
+  }
+}
 @media (not (-moz-bool-pref: "userChrome.icon.disabled")) and (-moz-bool-pref: "userChrome.icon.menu") and (-moz-bool-pref: "userChrome.icon.context_menu") {
   #context-showonlythisframe {
     --menuitem-image: url("../icons/eye-show.svg");
diff --git a/css/leptonChromeESR.css b/css/leptonChromeESR.css
index fadf4ab..65b0030 100644
--- a/css/leptonChromeESR.css
+++ b/css/leptonChromeESR.css
@@ -12244,7 +12244,8 @@
         #context-sendpagetodevice-popup,
         #context-sendlinktodevice-popup,
         #frame > menupopup,
-        #spell-dictionaries-menu
+        #spell-dictionaries-menu,
+        #context-ask-chat > menupopup
       )
       > menuitem:not([type="checkbox"][checked="true"], [type="radio"]),
     .openintabs-menuitem,
@@ -12329,7 +12330,8 @@
         #context-sendpagetodevice-popup,
         #context-sendlinktodevice-popup,
         #frame > menupopup,
-        #spell-dictionaries-menu
+        #spell-dictionaries-menu,
+        #context-ask-chat > menupopup
       )
       > menuitem:not([type="checkbox"][checked="true"], [type="radio"]),
     .openintabs-menuitem,
@@ -12426,7 +12428,8 @@
           #context-sendpagetodevice-popup,
           #context-sendlinktodevice-popup,
           #frame > menupopup,
-          #spell-dictionaries-menu
+          #spell-dictionaries-menu,
+          #context-ask-chat > menupopup
         )
         > menuitem:not([type="checkbox"][checked="true"], [type="radio"]),
       .openintabs-menuitem,
@@ -12502,7 +12505,8 @@
               #context-sendpagetodevice-popup,
               #context-sendlinktodevice-popup,
               #frame > menupopup,
-              #spell-dictionaries-menu
+              #spell-dictionaries-menu,
+              #context-ask-chat > menupopup
             )
             > menuitem:not([type="checkbox"][checked="true"], [type="radio"]),
           .openintabs-menuitem,
@@ -12686,7 +12690,8 @@
           #context-sendpagetodevice-popup,
           #context-sendlinktodevice-popup,
           #frame > menupopup,
-          #spell-dictionaries-menu
+          #spell-dictionaries-menu,
+          #context-ask-chat > menupopup
         )
         > menuitem:not([type="checkbox"][checked="true"], [type="radio"]),
       .openintabs-menuitem,
@@ -13434,6 +13439,35 @@
           --menuitem-image: url("chrome://browser/skin/bookmark.svg");
         }
       }
+      /*= context-ask-chat =========================================================*/
+      #ask-chat-shortcuts .toolbarbutton-icon {
+        order: -1;
+        margin-inline-end: var(--arrowpanel-menuitem-margin-inline) !important;
+      }
+      #ask-chat-shortcuts .subviewbutton:nth-child(1) {
+        list-style-image: url("../icons/apps-list-detail.svg");
+      }
+      #ask-chat-shortcuts .subviewbutton:nth-child(2) {
+        list-style-image: url("../icons/code-text.svg");
+      }
+      #ask-chat-shortcuts .subviewbutton:nth-child(3) {
+        list-style-image: url("../icons/tetris-app.svg");
+      }
+      #ask-chat-shortcuts .subviewbutton:nth-child(4) {
+        list-style-image: url("../icons/arrow-up-exclamation.svg");
+      }
+      #context-ask-chat menuitem:nth-child(1) {
+        --menuitem-image: url("../icons/apps-list-detail.svg");
+      }
+      #context-ask-chat menuitem:nth-child(2) {
+        --menuitem-image: url("../icons/code-text.svg");
+      }
+      #context-ask-chat menuitem:nth-child(3) {
+        --menuitem-image: url("../icons/tetris-app.svg");
+      }
+      #context-ask-chat menuitem:nth-child(4) {
+        --menuitem-image: url("../icons/arrow-up-exclamation.svg");
+      }
       /*= main-context-menu-frame ==================================================*/
       #context-showonlythisframe {
         --menuitem-image: url("../icons/eye-show.svg");
diff --git a/icons/apps-list-detail.svg b/icons/apps-list-detail.svg
new file mode 100644
index 0000000..39a1bea
--- /dev/null
+++ b/icons/apps-list-detail.svg
@@ -0,0 +1,3 @@
+<svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 16 16" width="16" height="16" fill="context-fill" fill-opacity="context-fill-opacity">
+  <path d="M1.5 2A1.5 1.5 0 0 0 0 3.5v2A1.5 1.5 0 0 0 1.5 7h2A1.5 1.5 0 0 0 5 5.5v-2A1.5 1.5 0 0 0 3.5 2ZM1 3.5a.5.5 0 0 1 .5-.5h2a.5.5 0 0 1 .5.5v2a.5.5 0 0 1-.5.5h-2a.5.5 0 0 1-.5-.5ZM7.5 3a.5.5 0 0 0 0 1h8a.5.5 0 0 0 0-1Zm0 2a.5.5 0 0 0 0 1h6a.5.5 0 0 0 0-1Zm-6 4A1.5 1.5 0 0 0 0 10.5v2A1.5 1.5 0 0 0 1.5 14h2A1.5 1.5 0 0 0 5 12.5v-2A1.5 1.5 0 0 0 3.5 9ZM1 10.5a.5.5 0 0 1 .5-.5h2a.5.5 0 0 1 .5.5v2a.5.5 0 0 1-.5.5h-2a.5.5 0 0 1-.5-.5Zm6.5-.5a.5.5 0 0 0 0 1h8a.5.5 0 0 0 0-1Zm0 2a.5.5 0 0 0 0 1h6a.5.5 0 0 0 0-1Z"/>
+</svg>
diff --git a/icons/arrow-up-exclamation.svg b/icons/arrow-up-exclamation.svg
new file mode 100644
index 0000000..e5c57bf
--- /dev/null
+++ b/icons/arrow-up-exclamation.svg
@@ -0,0 +1,3 @@
+<svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 16 16" width="16" height="16" fill="context-fill" fill-opacity="context-fill-opacity">
+  <path d="M1.5 3a2 2 0 1 1 4 0c0 2.089-.745 4.925-1.183 6.405a.84.84 0 0 1-.816.595.842.842 0 0 1-.817-.597C2.246 7.915 1.5 5.065 1.5 3Zm2-3a3 3 0 0 0-3 3c0 2.227.789 5.204 1.225 6.685A1.842 1.842 0 0 0 3.5 11c.81 0 1.54-.518 1.775-1.31C5.712 8.213 6.5 5.25 6.5 3a3 3 0 0 0-3-3Zm-1 14a1 1 0 1 1 2 0 1 1 0 0 1-2 0zm1-2a2 2 0 1 0 0 4 2 2 0 0 0 0-4zm9-10.293V15.5a.5.5 0 0 1-1 0V1.707L9.354 3.854a.5.5 0 0 1-.708-.708l3-3a.5.5 0 0 1 .708 0l3 3a.5.5 0 0 1-.708.708z"/>
+</svg>
diff --git a/icons/code-text.svg b/icons/code-text.svg
new file mode 100644
index 0000000..f55df35
--- /dev/null
+++ b/icons/code-text.svg
@@ -0,0 +1,3 @@
+<svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 16 16" width="16" height="16" fill="context-fill" fill-opacity="context-fill-opacity">
+  <path d="M.5 3a.5.5 0 0 0 0 1H6a.5.5 0 0 0 0-1Zm3 3a.5.5 0 0 0 0 1h5a.5.5 0 0 0 0-1ZM2 9.5a.5.5 0 0 1 .5-.5h10a.5.5 0 0 1 0 1h-10a.5.5 0 0 1-.5-.5ZM.5 12a.5.5 0 0 0 0 1H9a.5.5 0 0 0 0-1Zm10-5.5A.5.5 0 0 1 11 6h3.5a.5.5 0 0 1 0 1H11a.5.5 0 0 1-.5-.5ZM8.5 3a.5.5 0 0 0 0 1h7a.5.5 0 0 0 0-1Z"/>
+</svg>
diff --git a/icons/tetris-app.svg b/icons/tetris-app.svg
new file mode 100644
index 0000000..ab0ef1b
--- /dev/null
+++ b/icons/tetris-app.svg
@@ -0,0 +1,3 @@
+<svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 16 16" width="16" height="16" fill="context-fill" fill-opacity="context-fill-opacity">
+  <path d="M5.25 0C4.56 0 4 .56 4 1.25v2.5a.25.25 0 0 1-.25.25h-2.5C.56 4 0 4.56 0 5.25v2.5C0 8.44.56 9 1.25 9h6.5C8.44 9 9 8.44 9 7.75v-2.5A.25.25 0 0 1 9.25 5h2.5C12.44 5 13 4.44 13 3.75v-2.5C13 .56 12.44 0 11.75 0Zm6.5 4H9V1h2.75a.25.25 0 0 1 .25.25v2.5a.25.25 0 0 1-.25.25ZM8.025 5c-.016.08-.025.164-.025.25v2.5a.25.25 0 0 1-.25.25H5V5ZM4 5v3H1.25A.25.25 0 0 1 1 7.75v-2.5A.25.25 0 0 1 1.25 5Zm.975-1c.016-.08.025-.164.025-.25v-2.5A.25.25 0 0 1 5.25 1H8v3Zm7.275 3C11.56 7 11 7.56 11 8.25v2.5a.25.25 0 0 1-.25.25h-6.5C3.56 11 3 11.56 3 12.25v2.5c0 .69.56 1.25 1.25 1.25h10.5c.69 0 1.25-.56 1.25-1.25v-6.5C16 7.56 15.44 7 14.75 7Zm-.275 4c.016-.08.025-.164.025-.25v-2.5a.25.25 0 0 1 .25-.25h2.5a.25.25 0 0 1 .25.25V11ZM12 12h3v2.75a.25.25 0 0 1-.25.25H12Zm-1 0v3H8v-3zm-4 0v3H4.25a.25.25 0 0 1-.25-.25v-2.5a.25.25 0 0 1 .25-.25Z"/>
+</svg>
diff --git a/src/icons/context_menu/_content_area.scss b/src/icons/context_menu/_content_area.scss
index 5c884cf..06fcdd3 100644
--- a/src/icons/context_menu/_content_area.scss
+++ b/src/icons/context_menu/_content_area.scss
@@ -292,6 +292,38 @@
   }
 }
 
+/*= context-ask-chat =========================================================*/
+#ask-chat-shortcuts .toolbarbutton-icon {
+  order: -1;
+  margin-inline-end: var(--arrowpanel-menuitem-margin-inline) !important;
+}
+#ask-chat-shortcuts .subviewbutton:nth-child(1) {
+  list-style-image: url("../icons/apps-list-detail.svg");
+}
+#ask-chat-shortcuts .subviewbutton:nth-child(2) {
+  list-style-image: url("../icons/code-text.svg");
+}
+#ask-chat-shortcuts .subviewbutton:nth-child(3) {
+  list-style-image: url("../icons/tetris-app.svg");
+}
+#ask-chat-shortcuts .subviewbutton:nth-child(4) {
+  list-style-image: url("../icons/arrow-up-exclamation.svg");
+}
+
+
+#context-ask-chat menuitem:nth-child(1) {
+  --menuitem-image: url("../icons/apps-list-detail.svg");
+}
+#context-ask-chat menuitem:nth-child(2) {
+  --menuitem-image: url("../icons/code-text.svg");
+}
+#context-ask-chat menuitem:nth-child(3) {
+  --menuitem-image: url("../icons/tetris-app.svg");
+}
+#context-ask-chat menuitem:nth-child(4) {
+  --menuitem-image: url("../icons/arrow-up-exclamation.svg");
+}
+
 /*= main-context-menu-frame ==================================================*/
 #context-showonlythisframe {
   --menuitem-image: url("../icons/eye-show.svg");
diff --git a/src/icons/layout/_menu_common.scss b/src/icons/layout/_menu_common.scss
index 3885026..ffa5d98 100644
--- a/src/icons/layout/_menu_common.scss
+++ b/src/icons/layout/_menu_common.scss
@@ -31,7 +31,7 @@ $_globalMenus: "#main-menubar > menu";
 $_libraryMenuitem: "menupopup:is(#organizeButtonPopup, #maintenanceButtonPopup) > #{$_iconMenuitem}";
 $_libraryMenu: "menupopup:is(#viewMenuPopup, #maintenanceButtonPopup) > #{$_iconMenu}";
 $_sendTabMenuPopup: "#context_sendTabToDevicePopupMenu, #context-sendpagetodevice-popup, #context-sendlinktodevice-popup";
-$_otherPopupMenuitem: "menupopup:is(#{$_sendTabMenuPopup}, #frame > menupopup, #spell-dictionaries-menu) > menuitem#{$_checkMenu}";
+$_otherPopupMenuitem: "menupopup:is(#{$_sendTabMenuPopup}, #frame > menupopup, #spell-dictionaries-menu, #context-ask-chat > menupopup) > menuitem#{$_checkMenu}";
 $_otherIconMenu: ".openintabs-menuitem, #blockedPopupDontShowMessage, #BMB_viewBookmarksToolbar, #sidebarMenu-popup:is(menupopup)";
 
 //-- Mixin ---------------------------------------------------------------------