diff --git a/quickstep/res/values/strings.xml b/quickstep/res/values/strings.xml
index 8e70a2b..7adba19 100644
--- a/quickstep/res/values/strings.xml
+++ b/quickstep/res/values/strings.xml
@@ -366,4 +366,9 @@
     <string name="header_default_app_title">App title</string>
     <!-- Content description for the header close button. [CHAR LIMIT=NONE] -->
     <string name="header_close_icon_description">Close button</string>
+
+    <!-- Label for pinning an item to the taskbar. [CHAR_LIMIT=20] -->
+    <string name="pin_to_taskbar">Pin to taskbar</string>
+    <!-- Label for unpinning an item from the taskbar. [CHAR_LIMIT=20] -->
+    <string name="unpin_from_taskbar">Unpin from taskbar</string>
 </resources>
diff --git a/quickstep/src/com/android/launcher3/taskbar/PinToTaskbarShortcut.kt b/quickstep/src/com/android/launcher3/taskbar/PinToTaskbarShortcut.kt
new file mode 100644
index 0000000..b9a211d
--- /dev/null
+++ b/quickstep/src/com/android/launcher3/taskbar/PinToTaskbarShortcut.kt
@@ -0,0 +1,42 @@
+/*
+ * Copyright (C) 2025 The Android Open Source Project
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package com.android.launcher3.taskbar
+
+import android.content.Context
+import android.view.View
+import com.android.launcher3.R
+import com.android.launcher3.model.data.ItemInfo
+import com.android.launcher3.popup.SystemShortcut
+import com.android.launcher3.views.ActivityContext
+
+/**
+ * A single menu item shortcut to allow users to pin an item to the taskbar and unpin an item from
+ * the taskbar.
+ */
+class PinToTaskbarShortcut<T>(target: T, itemInfo: ItemInfo?, originalView: View, isPin: Boolean) :
+    SystemShortcut<T>(
+        if (isPin) R.drawable.ic_pin else R.drawable.ic_unpin,
+        if (isPin) R.string.pin_to_taskbar else R.string.unpin_from_taskbar,
+        target,
+        itemInfo,
+        originalView,
+    ) where T : Context?, T : ActivityContext? {
+
+    override fun onClick(v: View?) {
+        // TODO(b/375648361): Pin/Unpin the item here.
+    }
+}
diff --git a/quickstep/src/com/android/launcher3/taskbar/TaskbarModelCallbacks.java b/quickstep/src/com/android/launcher3/taskbar/TaskbarModelCallbacks.java
index 6815f97..f2eeed5 100644
--- a/quickstep/src/com/android/launcher3/taskbar/TaskbarModelCallbacks.java
+++ b/quickstep/src/com/android/launcher3/taskbar/TaskbarModelCallbacks.java
@@ -203,6 +203,7 @@
             ItemInfo[] hotseatItemInfos, List<GroupTask> recentTasks) {
         mContainer.updateItems(hotseatItemInfos, recentTasks);
         mControllers.taskbarViewController.updateIconViewsRunningStates();
+        mControllers.taskbarPopupController.setHotseatInfosList(mHotseatItems);
     }
 
     /**
diff --git a/quickstep/src/com/android/launcher3/taskbar/TaskbarPopupController.java b/quickstep/src/com/android/launcher3/taskbar/TaskbarPopupController.java
index 5d8b821..80944bb 100644
--- a/quickstep/src/com/android/launcher3/taskbar/TaskbarPopupController.java
+++ b/quickstep/src/com/android/launcher3/taskbar/TaskbarPopupController.java
@@ -16,18 +16,20 @@
 package com.android.launcher3.taskbar;
 
 import static com.android.launcher3.LauncherSettings.Favorites.CONTAINER_ALL_APPS;
+import static com.android.launcher3.LauncherSettings.Favorites.CONTAINER_HOTSEAT;
 import static com.android.launcher3.model.data.AppInfo.COMPONENT_KEY_COMPARATOR;
-import static com.android.launcher3.popup.SystemShortcut.PIN_UNPIN_ITEM;
 import static com.android.launcher3.util.SplitConfigurationOptions.getLogEventForPosition;
 
 import android.content.Intent;
 import android.content.pm.LauncherApps;
 import android.graphics.Point;
 import android.util.Pair;
+import android.util.SparseArray;
 import android.view.MotionEvent;
 import android.view.View;
 
 import androidx.annotation.NonNull;
+import androidx.annotation.Nullable;
 
 import com.android.internal.logging.InstanceId;
 import com.android.launcher3.AbstractFloatingView;
@@ -88,6 +90,8 @@
     private TaskbarControllers mControllers;
     private boolean mAllowInitialSplitSelection;
     private AppInfo[] mAppInfosList;
+    // Saves the ItemInfos in the hotseat without the predicted items.
+    private SparseArray<ItemInfo> mHotseatInfosList;
     private ManageWindowsTaskbarShortcut<BaseTaskbarContext> mManageWindowsTaskbarShortcut;
 
 
@@ -189,6 +193,14 @@
                 .filter(Objects::nonNull)
                 .collect(Collectors.toList());
 
+        // TODO(b/375648361): Revisit to see if this can be implemented within getSystemShortcuts().
+        if (Flags.enablePinningAppWithContextMenu()) {
+            SystemShortcut shortcut = createPinShortcut(context, item, icon);
+            if (shortcut != null) {
+                systemShortcuts.add(0, shortcut);
+            }
+        }
+
         container = (PopupContainerWithArrow) context.getLayoutInflater().inflate(
                     R.layout.popup_container, context.getDragLayer(), false);
         container.populateAndShowRows(icon, deepShortcutCount, systemShortcuts);
@@ -212,9 +224,6 @@
         // append split options to APP_INFO shortcut if not in Desktop Windowing mode, the order
         // here will reflect in the popup
         ArrayList<SystemShortcut.Factory> shortcuts = new ArrayList<>();
-        if (Flags.enablePinningAppWithContextMenu()) {
-            shortcuts.add(PIN_UNPIN_ITEM);
-        }
         shortcuts.add(APP_INFO);
         if (!mControllers.taskbarDesktopModeController
                 .isInDesktopModeAndNotInOverview(mContext.getDisplayId())) {
@@ -233,6 +242,24 @@
         return shortcuts.stream();
     }
 
+    @Nullable
+    private SystemShortcut createPinShortcut(BaseTaskbarContext target, ItemInfo itemInfo,
+            BubbleTextView originalView) {
+        // Predicted items use {@code HotseatPredictionController.PinPrediction} shortcut to pin.
+        if (itemInfo.isPredictedItem()) {
+            return null;
+        }
+        if (itemInfo.container == CONTAINER_HOTSEAT) {
+            return new PinToTaskbarShortcut<>(target, itemInfo, originalView, false);
+        }
+        if (mHotseatInfosList.size()
+                < mContext.getTaskbarSpecsEvaluator().getNumShownHotseatIcons()) {
+            return new PinToTaskbarShortcut<>(target, itemInfo, originalView, true);
+        }
+
+        return null;
+    }
+
     @Override
     public void dumpLogs(String prefix, PrintWriter pw) {
         pw.println(prefix + "TaskbarPopupController:");
@@ -316,6 +343,10 @@
         return index < 0 ? null : mAppInfosList[index];
     }
 
+    public void setHotseatInfosList(SparseArray<ItemInfo> info) {
+        mHotseatInfosList = info;
+    }
+
     /**
      * Returns a stream of Multi Instance menu options if an app supports it.
      */
diff --git a/quickstep/src/com/android/launcher3/taskbar/customization/TaskbarSpecsEvaluator.kt b/quickstep/src/com/android/launcher3/taskbar/customization/TaskbarSpecsEvaluator.kt
index 822ca64..f1ed6c5 100644
--- a/quickstep/src/com/android/launcher3/taskbar/customization/TaskbarSpecsEvaluator.kt
+++ b/quickstep/src/com/android/launcher3/taskbar/customization/TaskbarSpecsEvaluator.kt
@@ -26,6 +26,8 @@
     numColumns: Int = taskbarActivityContext.deviceProfile.inv.numColumns,
 ) {
     var taskbarIconSize: TaskbarIconSize = getIconSizeByGrid(numColumns, numRows)
+    val numShownHotseatIcons
+        get() = taskbarActivityContext.deviceProfile.numShownHotseatIcons
 
     // TODO(b/341146605) : initialize it to taskbar container in later cl.
     private var taskbarContainer: List<TaskbarContainer> = emptyList()
diff --git a/quickstep/src/com/android/launcher3/uioverrides/QuickstepLauncher.java b/quickstep/src/com/android/launcher3/uioverrides/QuickstepLauncher.java
index 019e746..cac49f0 100644
--- a/quickstep/src/com/android/launcher3/uioverrides/QuickstepLauncher.java
+++ b/quickstep/src/com/android/launcher3/uioverrides/QuickstepLauncher.java
@@ -48,7 +48,6 @@
 import static com.android.launcher3.popup.SystemShortcut.BUBBLE_SHORTCUT;
 import static com.android.launcher3.popup.SystemShortcut.DONT_SUGGEST_APP;
 import static com.android.launcher3.popup.SystemShortcut.INSTALL;
-import static com.android.launcher3.popup.SystemShortcut.PIN_UNPIN_ITEM;
 import static com.android.launcher3.popup.SystemShortcut.PRIVATE_PROFILE_INSTALL;
 import static com.android.launcher3.popup.SystemShortcut.UNINSTALL_APP;
 import static com.android.launcher3.popup.SystemShortcut.WIDGETS;
@@ -475,9 +474,6 @@
         List<SystemShortcut.Factory> shortcuts = new ArrayList(Arrays.asList(
                 APP_INFO, WellbeingModel.SHORTCUT_FACTORY, mHotseatPredictionController));
 
-        if (Flags.enablePinningAppWithContextMenu()) {
-            shortcuts.add(0, PIN_UNPIN_ITEM);
-        }
         shortcuts.addAll(getSplitShortcuts());
         shortcuts.add(WIDGETS);
         shortcuts.add(INSTALL);
diff --git a/res/drawable/ic_unpin.xml b/res/drawable/ic_unpin.xml
new file mode 100644
index 0000000..557b4f9
--- /dev/null
+++ b/res/drawable/ic_unpin.xml
@@ -0,0 +1,28 @@
+<?xml version="1.0" encoding="utf-8"?><!--
+  ~ Copyright (C) 2025 The Android Open Source Project
+  ~
+  ~ Licensed under the Apache License, Version 2.0 (the "License");
+  ~ you may not use this file except in compliance with the License.
+  ~ You may obtain a copy of the License at
+  ~
+  ~      http://www.apache.org/licenses/LICENSE-2.0
+  ~
+  ~ Unless required by applicable law or agreed to in writing, software
+  ~ distributed under the License is distributed on an "AS IS" BASIS,
+  ~ WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+  ~ See the License for the specific language governing permissions and
+  ~ limitations under the License.
+  -->
+<vector xmlns:android="http://schemas.android.com/apk/res/android"
+    android:width="24dp"
+    android:height="24dp"
+    android:viewportWidth="24"
+    android:viewportHeight="24">
+  <group>
+    <clip-path
+        android:pathData="M0,0h24v24h-24z"/>
+    <path
+        android:pathData="M17,3V5H16V13.175L14,11.175V5H10V7.175L7.825,5L7,4.175V3H17ZM12,23L11,22V16H6V14L8,12V10.85L1.4,4.2L2.8,2.8L21.2,21.2L19.75,22.6L13.15,16H13V22L12,23ZM8.85,14H11.15L10.05,12.9L10,12.85L8.85,14Z"
+        android:fillColor="#FF000000"/>
+  </group>
+</vector>
diff --git a/res/values/strings.xml b/res/values/strings.xml
index a02516a..3acdb0d 100644
--- a/res/values/strings.xml
+++ b/res/values/strings.xml
@@ -235,8 +235,6 @@
     <string name="pin_prediction">Pin Prediction</string>
     <!-- Label for bubbling a launcher item. [CHAR_LIMIT=20] -->
     <string name="bubble">Bubble</string>
-    <!-- Label for pinning an item to the taskbar. [CHAR_LIMIT=20] -->
-    <string name="pin_to_taskbar">Pin to taskbar</string>
 
     <!-- Permissions: -->
     <skip />
diff --git a/src/com/android/launcher3/popup/SystemShortcut.java b/src/com/android/launcher3/popup/SystemShortcut.java
index 7e08c6e..b7efdec 100644
--- a/src/com/android/launcher3/popup/SystemShortcut.java
+++ b/src/com/android/launcher3/popup/SystemShortcut.java
@@ -210,30 +210,6 @@
         }
     }
 
-    public static final Factory<ActivityContext> PIN_UNPIN_ITEM =
-            (context, itemInfo, originalView) -> {
-                // Predicted items use {@code HotseatPredictionController.PinPrediction} shortcut
-                // to pin.
-                if (itemInfo.isPredictedItem()) {
-                    return null;
-                }
-                return new PinUnpinItem<>(context, itemInfo, originalView);
-            };
-
-    private static class PinUnpinItem<T extends ActivityContext> extends SystemShortcut<T> {
-        PinUnpinItem(T target, ItemInfo itemInfo, @NonNull View originalView) {
-            // TODO(b/375648361): Check the pin state of the item to determine if the pin or the
-            //  unpin option should be used.
-            super(R.drawable.ic_pin, R.string.pin_to_taskbar, target,
-                    itemInfo, originalView);
-        }
-
-        @Override
-        public void onClick(View view) {
-            // TODO(b/375648361): Pin/Unpin the item here.
-        }
-    }
-
     public static final Factory<ActivityContext> PRIVATE_PROFILE_INSTALL =
             (context, itemInfo, originalView) -> {
                 if (originalView == null) {