diff --git a/HellionChat/PluginHostFactory.cs b/HellionChat/PluginHostFactory.cs
index f56ffbd..c66290b 100644
--- a/HellionChat/PluginHostFactory.cs
+++ b/HellionChat/PluginHostFactory.cs
@@ -198,7 +198,8 @@ internal static class PluginHostFactory
             sp.GetRequiredService<Ui.Components.Sidebar>(),
             sp.GetRequiredService<Ui.Components.MessageList>(),
             sp.GetRequiredService<Ui.Components.InputBar>(),
-            sp.GetRequiredService<Ui.Components.StatusBar>()
+            sp.GetRequiredService<Ui.Components.StatusBar>(),
+            sp.GetRequiredService<Lender<PayloadHandler>>()
         ));
         services.AddSingleton(sp => new Integrations.FailedTellNotifier(
             sp.GetRequiredService<ILogger<Integrations.FailedTellNotifier>>()
diff --git a/HellionChat/Ui/Components/MessageList.cs b/HellionChat/Ui/Components/MessageList.cs
index 965d50a..049fce1 100644
--- a/HellionChat/Ui/Components/MessageList.cs
+++ b/HellionChat/Ui/Components/MessageList.cs
@@ -31,6 +31,10 @@ internal sealed class MessageList
         _handler = handler;
     }
 
+    // Delegates to PayloadHandler.Draw for per-frame popup tick; PayloadHandler.Draw doesn't auto-fire
+    // so MainWindow's draw loop must invoke it explicitly to render right-click context popups.
+    internal void DrawHandlerPopups() => _handler?.Draw();
+
     public MessageList(
         ThemeRegistry themes,
         TokenResolver resolver,
diff --git a/HellionChat/Ui/Windows/MainWindow.cs b/HellionChat/Ui/Windows/MainWindow.cs
index c1293ca..a434eb7 100644
--- a/HellionChat/Ui/Windows/MainWindow.cs
+++ b/HellionChat/Ui/Windows/MainWindow.cs
@@ -2,6 +2,7 @@ using System.Numerics;
 using Dalamud.Bindings.ImGui;
 using Dalamud.Interface.Utility.Raii;
 using Dalamud.Interface.Windowing;
+using HellionChat.Util;
 
 namespace HellionChat.Ui.Windows;
 
@@ -26,6 +27,7 @@ internal sealed class MainWindow : Window
     private readonly Components.MessageList _messages;
     private readonly Components.InputBar _input;
     private readonly Components.StatusBar _status;
+    private readonly Lender<PayloadHandler> _handlerLender;
 
     private Tab? _activeTab;
 
@@ -38,7 +40,8 @@ internal sealed class MainWindow : Window
         Components.Sidebar sidebar,
         Components.MessageList messages,
         Components.InputBar input,
-        Components.StatusBar status
+        Components.StatusBar status,
+        Lender<PayloadHandler> handlerLender
     )
         : base($"{Plugin.PluginName}###hellion-main")
     {
@@ -47,6 +50,7 @@ internal sealed class MainWindow : Window
         _messages = messages;
         _input = input;
         _status = status;
+        _handlerLender = handlerLender;
 
         Size = new Vector2(DefaultWidth, DefaultHeight);
         SizeCondition = ImGuiCond.FirstUseEver;
@@ -92,6 +96,9 @@ internal sealed class MainWindow : Window
             LastViewport = ImGui.GetWindowViewport().Handle;
         }
 
+        // Primary pool-reset path; InputPreview has a defensive fallback for the MainWindow-closed edge case.
+        _handlerLender.ResetCounter();
+
         // First-frame seed: the active tab defaults to the first persisted
         // tab so the message list isn't empty on a clean session.
         if (_activeTab is null && Plugin.Config.Tabs.Count > 0)
@@ -105,6 +112,7 @@ internal sealed class MainWindow : Window
                 DrawBody();
         }
 
+        _messages.DrawHandlerPopups();
         _status.Draw(_activeTab);
     }