diff --git a/HellionChat/Ui/ChatLogWindow.cs b/HellionChat/Ui/ChatLogWindow.cs
index 168e41b..9318935 100644
--- a/HellionChat/Ui/ChatLogWindow.cs
+++ b/HellionChat/Ui/ChatLogWindow.cs
@@ -14,6 +14,7 @@ using Dalamud.Interface.Utility.Raii;
 using Dalamud.Interface.Windowing;
 using Dalamud.Memory;
 using FFXIVClientStructs.FFXIV.Client.UI;
+using FFXIVClientStructs.FFXIV.Client.UI.Agent;
 using HellionChat.Code;
 using HellionChat.GameFunctions;
 using HellionChat.GameFunctions.Types;
@@ -1122,6 +1123,27 @@ public sealed class ChatLogWindow : Window
                     using var pushedColor = ImRaii.PushColor(ImGuiCol.Text, normalColor);
                     if (ImGui.Selectable(Language.ChatLog_HideChat))
                         UserHide();
+
+                    // Insert game text-macro tokens. The game expands <flag>/<item> at
+                    // send time, so inserting literal token text is enough. Each entry is
+                    // disabled when its precondition is unmet (no map flag, no linked item)
+                    // so the inserted token cannot expand to nothing.
+                    unsafe
+                    {
+                        var flagSet = AgentMap.Instance()->FlagMarkerCount > 0;
+                        using (ImRaii.Disabled(!flagSet))
+                        {
+                            if (ImGui.Selectable(HellionStrings.ChatLog_Insert_MapFlag))
+                                Chat += "<flag>";
+                        }
+
+                        var itemSet = AgentChatLog.Instance()->LinkedItem.ItemId != 0;
+                        using (ImRaii.Disabled(!itemSet))
+                        {
+                            if (ImGui.Selectable(HellionStrings.ChatLog_Insert_ItemLink))
+                                Chat += "<item>";
+                        }
+                    }
                 }
             }
         }