diff --git a/HellionChat/Ui/ChatLogWindow.cs b/HellionChat/Ui/ChatLogWindow.cs
index 9318935..072cb5f 100644
--- a/HellionChat/Ui/ChatLogWindow.cs
+++ b/HellionChat/Ui/ChatLogWindow.cs
@@ -1130,18 +1130,29 @@ public sealed class ChatLogWindow : Window
                     // so the inserted token cannot expand to nothing.
                     unsafe
                     {
-                        var flagSet = AgentMap.Instance()->FlagMarkerCount > 0;
+                        // Null-check before deref: pointers can be null during zone transitions.
+                        var agentMap = AgentMap.Instance();
+                        var flagSet = agentMap != null && agentMap->FlagMarkerCount > 0;
                         using (ImRaii.Disabled(!flagSet))
                         {
                             if (ImGui.Selectable(HellionStrings.ChatLog_Insert_MapFlag))
+                            {
                                 Chat += "<flag>";
+                                Activate = true;
+                                ActivatePos = Chat.Length;
+                            }
                         }
 
-                        var itemSet = AgentChatLog.Instance()->LinkedItem.ItemId != 0;
+                        var agentChat = AgentChatLog.Instance();
+                        var itemSet = agentChat != null && agentChat->LinkedItem.ItemId != 0;
                         using (ImRaii.Disabled(!itemSet))
                         {
                             if (ImGui.Selectable(HellionStrings.ChatLog_Insert_ItemLink))
+                            {
                                 Chat += "<item>";
+                                Activate = true;
+                                ActivatePos = Chat.Length;
+                            }
                         }
                     }
                 }