diff --git a/packages/bbrt/src/llm/conversation.ts b/packages/bbrt/src/llm/conversation.ts
index 4facef3ede..19cc4790fb 100644
--- a/packages/bbrt/src/llm/conversation.ts
+++ b/packages/bbrt/src/llm/conversation.ts
@@ -24,6 +24,8 @@ import type { JsonSerializableObject } from "../util/json-serializable.js";
 import { coercePresentableError } from "../util/presentable-error.js";
 import type { Result } from "../util/result.js";
 
+const MAX_TOOL_ITERATIONS = 5;
+
 export interface ConversationOptions {
   state: ReactiveSessionState;
   drivers: Map<string, BBRTDriver>;
@@ -99,25 +101,22 @@ export class Conversation {
 
     const done = (async (): Promise<void> => {
       const activeTools = await this.#getActiveTools();
-      const { functionCalls } = await this.#callModel(
-        driver.value,
-        activeTools,
-        initialTimestamp,
-        systemPrompt
-      );
-      if (functionCalls.length > 0) {
-        await Promise.all(
-          functionCalls.map((call) =>
-            this.#executeFunctionCall(call, activeTools)
+      let remainingModelCalls = 1 + Math.max(0, MAX_TOOL_ITERATIONS);
+      let functionCalls: ReactiveFunctionCallState[];
+      do {
+        const allowFunctionCalls = remainingModelCalls > 1;
+        functionCalls = (
+          await this.#callModel(
+            driver.value,
+            allowFunctionCalls ? activeTools : undefined,
+            systemPrompt
           )
-        );
-        await this.#callModel(
-          driver.value,
-          undefined,
-          this.#clock.now(),
-          systemPrompt
-        );
-      }
+        ).functionCalls;
+        if (functionCalls.length > 0) {
+          await this.#executeFunctionCalls(functionCalls, activeTools);
+        }
+        remainingModelCalls--;
+      } while (functionCalls.length > 0);
       this.#status = "ready";
     })();
 
@@ -162,9 +161,9 @@ export class Conversation {
   async #callModel(
     driver: BBRTDriver,
     tools: Map<string, BBRTTool> | undefined,
-    timestamp: number,
     systemPrompt: string
   ): Promise<{ functionCalls: ReactiveFunctionCallState[] }> {
+    const timestamp = this.#clock.now();
     // TODO(aomarks) This is a little weird. The natural thing to do would seem
     // to be to create a ReactiveSessionEventTurn, and pass it in. But in fact
     // our State constructors treat all initializer data as pure data, so that
@@ -187,7 +186,8 @@ export class Conversation {
     this.state.events.push(event);
     const turn = (event.detail as ReactiveSessionEventTurn).turn;
     const functionCalls = [];
-    // Don't include the pending turn we just created.
+    // Don't include the pending turn we just created. We want the user to see
+    // it, but not the model.
     const slice = this.state.turns.slice(0, -1);
     try {
       const chunks = driver.send({
@@ -197,7 +197,7 @@ export class Conversation {
       });
       for await (const chunk of chunks) {
         if (chunk.kind === "function-call") {
-          if (tools !== undefined) {
+          if (tools?.size) {
             const call = new ReactiveFunctionCallState(chunk.call);
             functionCalls.push(call);
             turn.chunks.push({
@@ -227,6 +227,15 @@ export class Conversation {
     return { functionCalls };
   }
 
+  #executeFunctionCalls(
+    calls: ReactiveFunctionCallState[],
+    tools: Map<string, BBRTTool>
+  ): Promise<void[]> {
+    return Promise.all(
+      calls.map((call) => this.#executeFunctionCall(call, tools))
+    );
+  }
+
   async #executeFunctionCall(
     call: ReactiveFunctionCallState,
     tools: Map<string, BBRTTool>