diff --git a/packages/bolt/app/lib/.server/llm/constants.ts b/packages/bolt/app/lib/.server/llm/constants.ts
index bfe772e..b24acdf 100644
--- a/packages/bolt/app/lib/.server/llm/constants.ts
+++ b/packages/bolt/app/lib/.server/llm/constants.ts
@@ -1,2 +1,5 @@
 // see https://docs.anthropic.com/en/docs/about-claude/models
 export const MAX_TOKENS = 8192;
+
+// limits the number of model responses that can be returned in a single request
+export const MAX_RESPONSE_SEGMENTS = 2;
diff --git a/packages/bolt/app/lib/.server/llm/prompts.ts b/packages/bolt/app/lib/.server/llm/prompts.ts
index f811376..e691066 100644
--- a/packages/bolt/app/lib/.server/llm/prompts.ts
+++ b/packages/bolt/app/lib/.server/llm/prompts.ts
@@ -1,4 +1,5 @@
 import { WORK_DIR } from '../../../utils/constants';
+import { stripIndents } from '../../../utils/stripIndent';
 
 export const getSystemPrompt = (cwd: string = WORK_DIR) => `
 You are Bolt, an expert AI assistant and exceptional senior software developer with vast knowledge across multiple programming languages, frameworks, and best practices.
@@ -198,3 +199,8 @@ Here are some examples of correct usage of artifacts:
   </example>
 </examples>
 `;
+
+export const CONTINUE_PROMPT = stripIndents`
+  Continue your prior response. IMPORTANT: Immediately begin from where you left off without any interruptions.
+  Do not repeat any content, including artifact and action tags.
+`;
diff --git a/packages/bolt/app/lib/.server/llm/switchable-stream.ts b/packages/bolt/app/lib/.server/llm/switchable-stream.ts
new file mode 100644
index 0000000..bedc883
--- /dev/null
+++ b/packages/bolt/app/lib/.server/llm/switchable-stream.ts
@@ -0,0 +1,65 @@
+export default class SwitchableStream extends TransformStream {
+  private _controller: TransformStreamDefaultController | null = null;
+  private _currentReader: ReadableStreamDefaultReader | null = null;
+  private _switches = 0;
+
+  constructor() {
+    let controllerRef: TransformStreamDefaultController | undefined;
+
+    super({
+      start(controller) {
+        controllerRef = controller;
+      },
+    });
+
+    if (controllerRef === undefined) {
+      throw new Error('Controller not properly initialized');
+    }
+
+    this._controller = controllerRef;
+  }
+
+  async switchSource(newStream: ReadableStream) {
+    if (this._currentReader) {
+      await this._currentReader.cancel();
+    }
+
+    this._currentReader = newStream.getReader();
+
+    this._pumpStream();
+
+    this._switches++;
+  }
+
+  private async _pumpStream() {
+    if (!this._currentReader || !this._controller) {
+      throw new Error('Stream is not properly initialized');
+    }
+
+    try {
+      while (true) {
+        const { done, value } = await this._currentReader.read();
+
+        if (done) {
+          break;
+        }
+
+        this._controller.enqueue(value);
+      }
+    } catch (error) {
+      this._controller.error(error);
+    }
+  }
+
+  close() {
+    if (this._currentReader) {
+      this._currentReader.cancel();
+    }
+
+    this._controller?.terminate();
+  }
+
+  get switches() {
+    return this._switches;
+  }
+}
diff --git a/packages/bolt/app/routes/api.chat.ts b/packages/bolt/app/routes/api.chat.ts
index 3974b6e..b75d4e5 100644
--- a/packages/bolt/app/routes/api.chat.ts
+++ b/packages/bolt/app/routes/api.chat.ts
@@ -1,12 +1,40 @@
 import { type ActionFunctionArgs } from '@remix-run/cloudflare';
-import { streamText, type Messages } from '../lib/.server/llm/stream-text';
+import { MAX_RESPONSE_SEGMENTS } from '../lib/.server/llm/constants';
+import { CONTINUE_PROMPT } from '../lib/.server/llm/prompts';
+import { streamText, type Messages, type StreamingOptions } from '../lib/.server/llm/stream-text';
+import SwitchableStream from '../lib/.server/llm/switchable-stream';
+import { StreamingTextResponse } from 'ai';
 
 export async function action({ context, request }: ActionFunctionArgs) {
   const { messages } = await request.json<{ messages: Messages }>();
+  const stream = new SwitchableStream();
 
   try {
-    const result = await streamText(messages, context.cloudflare.env, { toolChoice: 'none' });
-    return result.toAIStreamResponse();
+    const options: StreamingOptions = {
+      toolChoice: 'none',
+      onFinish: async ({ text: content, finishReason }) => {
+        if (finishReason !== 'length') {
+          return stream.close();
+        }
+
+        if (stream.switches >= MAX_RESPONSE_SEGMENTS) {
+          throw Error('Cannot continue message: maximum segments reached');
+        }
+
+        messages.push({ role: 'assistant', content });
+        messages.push({ role: 'user', content: CONTINUE_PROMPT });
+
+        const result = await streamText(messages, context.cloudflare.env, options);
+
+        return stream.switchSource(result.toAIStream());
+      },
+    };
+
+    const result = await streamText(messages, context.cloudflare.env, options);
+
+    stream.switchSource(result.toAIStream());
+
+    return new StreamingTextResponse(stream.readable);
   } catch (error) {
     console.log(error);