diff --git a/server-cloudflare/models/openai.ts b/server-cloudflare/models/openai.ts
index ff15b48..2f0ec61 100644
--- a/server-cloudflare/models/openai.ts
+++ b/server-cloudflare/models/openai.ts
@@ -1,7 +1,7 @@
 import { DurableObject } from "cloudflare:workers";
 import type { Env } from "../src/types";
 import { createOpusPacketizer } from "../src/opus";
-import { getSystemPrompt } from "../src/prompt";
+import { getFirstMessagePrompt, getSystemPrompt } from "../src/prompt";
 
 const AUDIO_OUTPUT_SAMPLE_RATE = 24_000;
 
@@ -42,15 +42,20 @@ async function transcribePcm(env: Env, audio: Uint8Array): Promise<string> {
 
 async function generateOpenAIReply(
   env: Env,
-  transcript: string,
+  transcript: string | null,
   history: OpenAIChatMessage[],
 ): Promise<string> {
   const messages: OpenAIChatMessage[] = [
     { role: "system", content: getSystemPrompt(env) },
     ...history,
-    { role: "user", content: transcript },
   ];
 
+  if (transcript && transcript.trim().length > 0) {
+    messages.push({ role: "user", content: transcript });
+  } else {
+    messages.push({ role: "user", content: getFirstMessagePrompt(env) });
+  }
+
   const response = await fetch("https://api.openai.com/v1/chat/completions", {
     method: "POST",
     headers: {
@@ -98,6 +103,7 @@ export class ElatoOpenAiVoiceAgent extends DurableObject<Env> {
   private audioBuffer = new Uint8Array(0);
   private isGenerating = false;
   private opusPromise: Promise<Awaited<ReturnType<typeof createOpusPacketizer>>> | null = null;
+  private hasStartedConversation = false;
 
   constructor(ctx: DurableObjectState, env: Env) {
     super(ctx, env);
@@ -130,35 +136,8 @@ export class ElatoOpenAiVoiceAgent extends DurableObject<Env> {
     return this.opusPromise;
   }
 
-  private async handleTurn(
-    websocket: WebSocket,
-  ) {
+  private async streamAssistantReply(websocket: WebSocket, reply: string) {
     const opus = await this.getOpusPacketizer(websocket);
-    const pcm = this.audioBuffer;
-    this.resetBufferedAudio();
-
-    if (pcm.byteLength === 0) {
-      return;
-    }
-
-    websocket.send(createServerMessage("AUDIO.COMMITTED"));
-
-    const transcript = await transcribePcm(this.env, pcm);
-    if (!transcript) {
-      websocket.send(createServerMessage("RESPONSE.ERROR"));
-      return;
-    }
-    /* Add user transcript DB call here */
-
-    const session = await this.loadSessionState();
-    const reply = await generateOpenAIReply(this.env, transcript, session.history);
-    session.history.push(
-      { role: "user", content: transcript },
-      { role: "assistant", content: reply },
-    );
-    await this.saveSessionState(session);
-    /* Add AI transcript DB call here */
-
     opus.reset();
     websocket.send(createServerMessage("RESPONSE.CREATED"));
 
@@ -184,6 +163,58 @@ export class ElatoOpenAiVoiceAgent extends DurableObject<Env> {
     }
   }
 
+  private async handleTurn(
+    websocket: WebSocket,
+  ) {
+    const pcm = this.audioBuffer;
+    this.resetBufferedAudio();
+
+    if (pcm.byteLength === 0) {
+      return;
+    }
+
+    websocket.send(createServerMessage("AUDIO.COMMITTED"));
+
+    const transcript = await transcribePcm(this.env, pcm);
+    if (!transcript) {
+      websocket.send(createServerMessage("RESPONSE.ERROR"));
+      return;
+    }
+    /* Add user transcript DB call here */
+
+    const session = await this.loadSessionState();
+    const reply = await generateOpenAIReply(this.env, transcript, session.history);
+    session.history.push(
+      { role: "user", content: transcript },
+      { role: "assistant", content: reply },
+    );
+    await this.saveSessionState(session);
+    /* Add AI transcript DB call here */
+    await this.streamAssistantReply(websocket, reply);
+  }
+
+  private async startInitialTurn(websocket: WebSocket) {
+    if (this.hasStartedConversation || this.isGenerating) {
+      return;
+    }
+
+    this.hasStartedConversation = true;
+    this.isGenerating = true;
+
+    try {
+      const session = await this.loadSessionState();
+      const reply = await generateOpenAIReply(this.env, null, session.history);
+      session.history.push({ role: "assistant", content: reply });
+      await this.saveSessionState(session);
+      /* Add AI transcript DB call here */
+      await this.streamAssistantReply(websocket, reply);
+    } catch {
+      websocket.send(createServerMessage("RESPONSE.ERROR"));
+    } finally {
+      this.isGenerating = false;
+    }
+  }
+
   async fetch(request: Request): Promise<Response> {
     if (request.headers.get("Upgrade") !== "websocket") {
       return new Response("Expected websocket", { status: 426 });
@@ -194,6 +225,7 @@ export class ElatoOpenAiVoiceAgent extends DurableObject<Env> {
     server.accept();
 
     server.send(JSON.stringify(createAuthMessage()));
+    void this.startInitialTurn(server);
 
     server.addEventListener("message", (event) => {
       void this.ctx.blockConcurrencyWhile(async () => {
diff --git a/server-cloudflare/src/prompt.ts b/server-cloudflare/src/prompt.ts
index ccd51d3..3d966a5 100644
--- a/server-cloudflare/src/prompt.ts
+++ b/server-cloudflare/src/prompt.ts
@@ -3,6 +3,13 @@ import type { Env } from "./types";
 const DEFAULT_PROMPT =
   "You are an Elato voice companion. Keep responses concise, natural to speak aloud, and friendly for a realtime conversation.";
 
+const DEFAULT_FIRST_MESSAGE =
+  "Start the conversation now with a short spoken greeting. Introduce yourself naturally in one sentence.";
+
 export function getSystemPrompt(env: Env): string {
   return env.ELATO_OPENAI_SYSTEM_PROMPT?.trim() || DEFAULT_PROMPT;
 }
+
+export function getFirstMessagePrompt(env: Env): string {
+  return env.ELATO_OPENAI_FIRST_MESSAGE?.trim() || DEFAULT_FIRST_MESSAGE;
+}
diff --git a/server-cloudflare/src/types.ts b/server-cloudflare/src/types.ts
index 016c2d3..b2d8b9a 100644
--- a/server-cloudflare/src/types.ts
+++ b/server-cloudflare/src/types.ts
@@ -4,5 +4,6 @@ export interface Env {
   OPENAI_API_KEY: string;
   ELATO_OPENAI_MODEL?: string;
   ELATO_OPENAI_SYSTEM_PROMPT?: string;
+  ELATO_OPENAI_FIRST_MESSAGE?: string;
   ElatoOpenAiVoiceAgent: DurableObjectNamespace;
 }