diff --git a/ChatView/ChatModel.cpp b/ChatView/ChatModel.cpp
index 806249c..932d711 100644
--- a/ChatView/ChatModel.cpp
+++ b/ChatView/ChatModel.cpp
@@ -195,6 +195,10 @@ QJsonArray ChatModel::prepareMessagesForRequest(const QString &systemPrompt) con
         case ChatRole::Assistant:
             role = "assistant";
             break;
+        case ChatRole::Tool:
+        case ChatRole::FileEdit:
+            // Skip Tool and FileEdit messages - they are UI-only
+            continue;
         default:
             continue;
         }
diff --git a/ChatView/ClientInterface.cpp b/ChatView/ClientInterface.cpp
index 8782fbd..72ff35f 100644
--- a/ChatView/ClientInterface.cpp
+++ b/ChatView/ClientInterface.cpp
@@ -142,6 +142,10 @@ void ClientInterface::sendMessage(
 
     QVector<LLMCore::Message> messages;
     for (const auto &msg : m_chatModel->getChatHistory()) {
+        // Skip Tool and FileEdit messages - they are UI-only and should not be in API history
+        if (msg.role == ChatModel::ChatRole::Tool || msg.role == ChatModel::ChatRole::FileEdit) {
+            continue;
+        }
         messages.append({msg.role == ChatModel::ChatRole::User ? "user" : "assistant", msg.content});
     }
     context.history = messages;