diff --git a/core/core.ts b/core/core.ts
index f948491fc1..8f50d90e7f 100644
--- a/core/core.ts
+++ b/core/core.ts
@@ -474,6 +474,18 @@ export class Core {
       }
     });
 
+    on("llm/compileChat", async (msg) => {
+      const { title: modelName, messages, options } = msg.data;
+      const model = await this.configHandler.llmFromTitle(modelName);
+
+      const { compiledChatMessages, lastMessageTruncated } =
+        model.compileChatMessages(options, messages);
+      return {
+        compiledChatMessages,
+        lastMessageTruncated,
+      };
+    });
+
     on("llm/streamChat", (msg) =>
       llmStreamChat(
         this.configHandler,
diff --git a/core/index.d.ts b/core/index.d.ts
index dd96d16995..48cefeb6ca 100644
--- a/core/index.d.ts
+++ b/core/index.d.ts
@@ -132,6 +132,7 @@ export interface ILLM extends LLMOptions {
     messages: ChatMessage[],
     signal: AbortSignal,
     options?: LLMFullCompletionOptions,
+    messageOptions?: MessageOptions,
   ): AsyncGenerator<ChatMessage, PromptLog>;
 
   chat(
@@ -140,6 +141,11 @@ export interface ILLM extends LLMOptions {
     options?: LLMFullCompletionOptions,
   ): Promise<ChatMessage>;
 
+  compileChatMessages(
+    options: LLMFullCompletionOptions,
+    messages: ChatMessage[],
+  ): { compiledChatMessages: ChatMEssage[]; lastMessageTruncated: boolean };
+
   embed(chunks: string[]): Promise<number[][]>;
 
   rerank(query: string, chunks: Chunk[]): Promise<number[]>;
@@ -1388,3 +1394,7 @@ export interface TerminalOptions {
   reuseTerminal?: boolean;
   terminalName?: string;
 }
+
+export interface MessageOptions {
+  precompiled: boolean;
+}
diff --git a/core/llm/countTokens.ts b/core/llm/countTokens.ts
index 2fc01f9b8b..ac1978fff0 100644
--- a/core/llm/countTokens.ts
+++ b/core/llm/countTokens.ts
@@ -251,13 +251,15 @@ function pruneChatHistory(
   chatHistory: ChatMessage[],
   contextLength: number,
   tokensForCompletion: number,
-): ChatMessage[] {
+): { prunedChatHistory: ChatMessage[]; lastMessageTruncated: boolean } {
   let totalTokens =
     tokensForCompletion +
     chatHistory.reduce((acc, message) => {
       return acc + countChatMessageTokens(modelName, message);
     }, 0);
 
+  let lastMessageTruncated = false;
+
   // 0. Prune any messages that take up more than 1/3 of the context length
   const zippedMessagesAndTokens: [ChatMessage, number][] = [];
 
@@ -363,8 +365,10 @@ function pruneChatHistory(
       tokensForCompletion,
     );
     totalTokens = contextLength;
+    lastMessageTruncated = true;
   }
-  return chatHistory;
+
+  return { prunedChatHistory: chatHistory, lastMessageTruncated };
 }
 
 function messageIsEmpty(message: ChatMessage): boolean {
@@ -527,7 +531,7 @@ function compileChatMessages({
   functions: any[] | undefined;
   systemMessage: string | undefined;
   rules: Rule[];
-}): ChatMessage[] {
+}): { compiledChatMessages: ChatMessage[]; lastMessageTruncated: boolean } {
   let msgsCopy = msgs
     ? msgs
         .map((msg) => ({ ...msg }))
@@ -581,7 +585,7 @@ function compileChatMessages({
     }
   }
 
-  const history = pruneChatHistory(
+  const { prunedChatHistory: history, lastMessageTruncated } = pruneChatHistory(
     modelName,
     msgsCopy,
     contextLength,
@@ -595,7 +599,7 @@ function compileChatMessages({
 
   const flattenedHistory = flattenMessages(history);
 
-  return flattenedHistory;
+  return { compiledChatMessages: flattenedHistory, lastMessageTruncated };
 }
 
 export {
diff --git a/core/llm/index.ts b/core/llm/index.ts
index cc7d7123cf..c7aaaf59b8 100644
--- a/core/llm/index.ts
+++ b/core/llm/index.ts
@@ -18,6 +18,7 @@ import {
   ILLM,
   LLMFullCompletionOptions,
   LLMOptions,
+  MessageOptions,
   ModelCapability,
   ModelInstaller,
   PromptLog,
@@ -738,6 +739,15 @@ export abstract class BaseLLM implements ILLM {
     return { role: "assistant" as const, content: completion };
   }
 
+  compileChatMessages(
+    options: LLMFullCompletionOptions,
+    messages: ChatMessage[],
+  ) {
+    let { completionOptions } = this._parseCompletionOptions(options);
+    completionOptions = this._modifyCompletionOptions(completionOptions);
+    return this._compileChatMessages(completionOptions, messages);
+  }
+
   protected modifyChatBody(
     body: ChatCompletionCreateParams,
   ): ChatCompletionCreateParams {
@@ -762,13 +772,23 @@ export abstract class BaseLLM implements ILLM {
     _messages: ChatMessage[],
     signal: AbortSignal,
     options: LLMFullCompletionOptions = {},
+    messageOptions?: MessageOptions,
   ): AsyncGenerator<ChatMessage, PromptLog> {
     let { completionOptions, logEnabled } =
       this._parseCompletionOptions(options);
 
     completionOptions = this._modifyCompletionOptions(completionOptions);
 
-    const messages = this._compileChatMessages(completionOptions, _messages);
+    const { precompiled } = messageOptions ?? {};
+
+    let messages = _messages;
+    if (!precompiled) {
+      const { compiledChatMessages } = this._compileChatMessages(
+        completionOptions,
+        _messages,
+      );
+      messages = compiledChatMessages;
+    }
 
     const prompt = this.templateMessages
       ? this.templateMessages(messages)
diff --git a/core/llm/streamChat.ts b/core/llm/streamChat.ts
index 9b1ea87b3a..17332ce1dc 100644
--- a/core/llm/streamChat.ts
+++ b/core/llm/streamChat.ts
@@ -23,8 +23,13 @@ export async function* llmStreamChat(
     void TTS.kill();
   }
 
-  const { title, legacySlashCommandData, completionOptions, messages } =
-    msg.data;
+  const {
+    title,
+    legacySlashCommandData,
+    completionOptions,
+    messages,
+    messageOptions,
+  } = msg.data;
 
   const model = await configHandler.llmFromTitle(title);
 
@@ -113,6 +118,7 @@ export async function* llmStreamChat(
       messages,
       new AbortController().signal,
       completionOptions,
+      messageOptions,
     );
     let next = await gen.next();
     while (!next.done) {
diff --git a/core/protocol/core.ts b/core/protocol/core.ts
index 0213cd0e55..f043942e15 100644
--- a/core/protocol/core.ts
+++ b/core/protocol/core.ts
@@ -20,6 +20,7 @@ import type {
   FileSymbolMap,
   IdeSettings,
   LLMFullCompletionOptions,
+  MessageOptions,
   ModelDescription,
   PromptLog,
   RangeInFile,
@@ -115,12 +116,21 @@ export type ToCoreFromIdeOrWebviewProtocol = {
     },
     string,
   ];
+  "llm/compileChat": [
+    {
+      title: string;
+      messages: ChatMessage[];
+      options: LLMFullCompletionOptions;
+    },
+    { compiledChatMessages: ChatMessage[]; lastMessageTruncated: boolean },
+  ];
   "llm/listModels": [{ title: string }, string[] | undefined];
   "llm/streamChat": [
     {
       messages: ChatMessage[];
       completionOptions: LLMFullCompletionOptions;
       title: string;
+      messageOptions: MessageOptions;
       legacySlashCommandData?: {
         command: SlashCommandDescription;
         input: string;
diff --git a/core/protocol/passThrough.ts b/core/protocol/passThrough.ts
index 272a6d148b..cd22784156 100644
--- a/core/protocol/passThrough.ts
+++ b/core/protocol/passThrough.ts
@@ -35,6 +35,7 @@ export const WEBVIEW_TO_CORE_PASS_THROUGH: (keyof ToCoreFromWebviewProtocol)[] =
     "autocomplete/cancel",
     "autocomplete/accept",
     "tts/kill",
+    "llm/compileChat",
     "llm/complete",
     "llm/streamChat",
     "llm/listModels",
diff --git a/extensions/intellij/src/main/kotlin/com/github/continuedev/continueintellijextension/constants/MessageTypes.kt b/extensions/intellij/src/main/kotlin/com/github/continuedev/continueintellijextension/constants/MessageTypes.kt
index 60d2d3b338..083dbf9c8a 100644
--- a/extensions/intellij/src/main/kotlin/com/github/continuedev/continueintellijextension/constants/MessageTypes.kt
+++ b/extensions/intellij/src/main/kotlin/com/github/continuedev/continueintellijextension/constants/MessageTypes.kt
@@ -101,6 +101,7 @@ class MessageTypes {
             "autocomplete/cancel",
             "autocomplete/accept",
             "tts/kill",
+            "llm/compileChat",
             "llm/complete",
             "llm/streamChat",
             "llm/listModels",
diff --git a/gui/src/pages/gui/Chat.tsx b/gui/src/pages/gui/Chat.tsx
index 682671cbb1..06a3aa4b45 100644
--- a/gui/src/pages/gui/Chat.tsx
+++ b/gui/src/pages/gui/Chat.tsx
@@ -132,6 +132,9 @@ export function Chat() {
   const hasDismissedExploreDialog = useAppSelector(
     (state) => state.ui.hasDismissedExploreDialog,
   );
+  const warningMessage = useAppSelector(
+    (state) => state.session.warningMessage,
+  );
 
   useEffect(() => {
     // Cmd + Backspace to delete current step
@@ -394,6 +397,13 @@ export function Chat() {
             </ErrorBoundary>
           </div>
         ))}
+        {warningMessage.length > 0 && (
+          <div className="relative m-2 flex justify-center rounded-md border border-solid border-red-600 bg-transparent p-4">
+            <p className="thread-message text-red-500">
+              {`Warning: ${warningMessage}`}
+            </p>
+          </div>
+        )}
       </StepsDiv>
       <div className={"relative"}>
         {toolCallState?.status === "generated" && <ToolCallButtons />}
diff --git a/gui/src/redux/slices/sessionSlice.ts b/gui/src/redux/slices/sessionSlice.ts
index 0906fdd451..c426855131 100644
--- a/gui/src/redux/slices/sessionSlice.ts
+++ b/gui/src/redux/slices/sessionSlice.ts
@@ -56,6 +56,7 @@ type SessionState = {
   };
   activeToolStreamId?: [string, string];
   newestToolbarPreviewForInput: Record<string, string>;
+  warningMessage: string;
 };
 
 function isCodeToEditEqual(a: CodeToEdit, b: CodeToEdit) {
@@ -94,6 +95,7 @@ const initialState: SessionState = {
   },
   lastSessionId: undefined,
   newestToolbarPreviewForInput: {},
+  warningMessage: "",
 };
 
 export const sessionSlice = createSlice({
@@ -234,6 +236,7 @@ export const sessionSlice = createSlice({
     deleteMessage: (state, action: PayloadAction<number>) => {
       // Deletes the current assistant message and the previous user message
       state.history.splice(action.payload - 1, 2);
+      state.warningMessage = "";
     },
     updateHistoryItemAtIndex: (
       state,
@@ -679,6 +682,9 @@ export const sessionSlice = createSlice({
       state.newestToolbarPreviewForInput[payload.inputId] =
         payload.contextItemId;
     },
+    setWarningMessage: (state, action: PayloadAction<string>) => {
+      state.warningMessage = action.payload;
+    },
   },
   selectors: {
     selectIsGatheringContext: (state) => {
@@ -780,6 +786,7 @@ export const {
   deleteSessionMetadata,
   setNewestToolbarPreviewForInput,
   cycleMode,
+  setWarningMessage,
 } = sessionSlice.actions;
 
 export const {
diff --git a/gui/src/redux/thunks/streamNormalInput.ts b/gui/src/redux/thunks/streamNormalInput.ts
index afc80fbe46..05e9a9ac7b 100644
--- a/gui/src/redux/thunks/streamNormalInput.ts
+++ b/gui/src/redux/thunks/streamNormalInput.ts
@@ -9,7 +9,8 @@ import {
   addPromptCompletionPair,
   selectUseTools,
   setToolGenerated,
-  streamUpdate
+  setWarningMessage,
+  streamUpdate,
 } from "../slices/sessionSlice";
 import { ThunkApiType } from "../store";
 import { callTool } from "./callTool";
@@ -39,6 +40,34 @@ export const streamNormalInput = createAsyncThunk<
     }
     const includeTools = useTools && modelSupportsTools(defaultModel);
 
+    const res = await extra.ideMessenger.request("llm/compileChat", {
+      title: defaultModel.title,
+      messages,
+      options: includeTools
+        ? {
+            tools: state.config.config.tools.filter(
+              (tool) =>
+                toolSettings[tool.function.name] !== "disabled" &&
+                toolGroupSettings[tool.group] !== "exclude",
+            ),
+          }
+        : {},
+    });
+
+    if (res.status === "error") {
+      throw new Error(res.error);
+    }
+
+    const { compiledChatMessages, lastMessageTruncated } = res.content;
+
+    if (lastMessageTruncated) {
+      dispatch(
+        setWarningMessage(
+          "The provided context items are too large. They have been truncated to fit within the model's context length.",
+        ),
+      );
+    }
+
     // Send request
     const gen = extra.ideMessenger.llmStreamChat(
       {
@@ -52,8 +81,9 @@ export const streamNormalInput = createAsyncThunk<
             }
           : {},
         title: defaultModel.title,
-        messages,
+        messages: compiledChatMessages,
         legacySlashCommandData,
+        messageOptions: { precompiled: true },
       },
       streamAborter.signal,
     );