diff --git a/src/mcp_agent/llm/providers/augmented_llm_openai.py b/src/mcp_agent/llm/providers/augmented_llm_openai.py
index 59127a170..42c728f70 100644
--- a/src/mcp_agent/llm/providers/augmented_llm_openai.py
+++ b/src/mcp_agent/llm/providers/augmented_llm_openai.py
@@ -274,7 +274,9 @@ async def _openai_completion(
             # Calculate new conversation messages (excluding prompts)
             new_messages = messages[len(prompt_messages) :]
 
-            # Update conversation history
+            if system_prompt:
+                new_messages = new_messages[1:]
+
             self.history.set(new_messages)
 
         self._log_chat_finished(model=self.default_request_params.model)
diff --git a/tests/e2e/smoke/base/test_e2e_smoke.py b/tests/e2e/smoke/base/test_e2e_smoke.py
index d8321f7f0..c64191029 100644
--- a/tests/e2e/smoke/base/test_e2e_smoke.py
+++ b/tests/e2e/smoke/base/test_e2e_smoke.py
@@ -7,9 +7,9 @@
 from pydantic import BaseModel, Field
 
 from mcp_agent.core.prompt import Prompt
-from mcp_agent.llm.memory import Memory
 
 if TYPE_CHECKING:
+    from mcp_agent.llm.memory import Memory
     from mcp_agent.mcp.prompt_message_multipart import PromptMessageMultipart
 
 
@@ -74,7 +74,7 @@ async def test_open_ai_history(fast_agent, model_name):
     async def agent_function():
         async with fast.run() as agent:
             await agent.send("MESSAGE ONE")
-            await agent.send("MEESAGE TWO")
+            await agent.send("MESSAGE TWO")
 
             provider_history: Memory = agent.agent._llm.history
             multipart_history = agent.agent.message_history