diff --git a/x-pack/plugins/observability_ai_assistant/server/service/client/index.test.ts b/x-pack/plugins/observability_ai_assistant/server/service/client/index.test.ts
index 3e7660c427be7..41beecee82245 100644
--- a/x-pack/plugins/observability_ai_assistant/server/service/client/index.test.ts
+++ b/x-pack/plugins/observability_ai_assistant/server/service/client/index.test.ts
@@ -1250,11 +1250,15 @@ describe('Observability AI Assistant client', () => {
 
       await requestAlertsFunctionCall();
 
+      await requestAlertsFunctionCall();
+
+      await requestAlertsFunctionCall();
+
       await finished(stream);
     });
 
     it('executed the function no more than three times', () => {
-      expect(functionClientMock.executeFunction).toHaveBeenCalledTimes(3);
+      expect(functionClientMock.executeFunction).toHaveBeenCalledTimes(5);
     });
 
     it('does not give the LLM the choice to call a function anymore', () => {
diff --git a/x-pack/plugins/observability_ai_assistant/server/service/client/index.ts b/x-pack/plugins/observability_ai_assistant/server/service/client/index.ts
index 0e3927f82370d..c100cd05cd7ae 100644
--- a/x-pack/plugins/observability_ai_assistant/server/service/client/index.ts
+++ b/x-pack/plugins/observability_ai_assistant/server/service/client/index.ts
@@ -175,7 +175,7 @@ export class ObservabilityAIAssistantClient {
 
     let numFunctionsCalled: number = 0;
 
-    const MAX_FUNCTION_CALLS = 3;
+    const MAX_FUNCTION_CALLS = 5;
     const MAX_FUNCTION_RESPONSE_TOKEN_COUNT = 4000;
 
     const next = async (nextMessages: Message[]): Promise<void> => {