diff --git a/src/cleanlab_codex/internal/validator.py b/src/cleanlab_codex/internal/validator.py
index 8921673..e5aa518 100644
--- a/src/cleanlab_codex/internal/validator.py
+++ b/src/cleanlab_codex/internal/validator.py
@@ -2,11 +2,14 @@
 
 from typing import TYPE_CHECKING, Any, Optional, Sequence, cast
 
+from cleanlab_tlm.tlm import TLMResponse
 from cleanlab_tlm.utils.rag import Eval, TrustworthyRAGScore, get_default_evals
 
 from cleanlab_codex.types.validator import ThresholdedTrustworthyRAGScore
 
 if TYPE_CHECKING:
+    from cleanlab_tlm import TLM
+
     from cleanlab_codex.validator import BadResponseThresholds
 
 
@@ -21,6 +24,17 @@
     "context_sufficiency": "is_not_context_sufficient",
 }
 
+REWRITE_QUERY = """Given a conversational Message History and a Query, rewrite the Query to be a self-contained question. If the query is already self contained, return it as-is.
+
+Query: {query}
+
+--
+Message History: \n{messages}
+
+--
+Remember, return the Query as-is except in cases where the Query is missing key words or has content that should be additionally clarified."""
+REWRITE_QUERY_TRUSTWORTHINESS_THRESHOLD = 0.5
+
 
 def get_default_evaluations() -> list[Eval]:
     """Get the default evaluations for the TrustworthyRAG.
@@ -40,6 +54,16 @@ def get_default_trustworthyrag_config() -> dict[str, Any]:
     }
 
 
+def get_default_tlm_config() -> dict[str, Any]:
+    """Get the default configuration for the TLM."""
+
+    return {
+        "quality_preset": "medium",
+        "verbose": False,
+        "options": {"model": "gpt-4.1-nano"},
+    }
+
+
 def update_scores_based_on_thresholds(
     scores: TrustworthyRAGScore | Sequence[TrustworthyRAGScore], thresholds: BadResponseThresholds
 ) -> ThresholdedTrustworthyRAGScore:
@@ -108,3 +132,38 @@ def is_bad(metric: str) -> bool:
     if is_bad("trustworthiness"):
         return "hallucination"
     return "other_issues"
+
+
+def validate_messages(messages: Optional[list[dict[str, Any]]] = None) -> None:
+    """Validate the format of messages based on OpenAI."""
+
+    if messages is None:
+        return
+    if not isinstance(messages, list):
+        raise TypeError("Messages must be a list of dictionaries.")  # noqa: TRY003
+    for message in messages:
+        if not isinstance(message, dict) or "role" not in message or "content" not in message:
+            raise TypeError("Each message must be a dictionary containing 'role' and 'content' keys.")  # noqa: TRY003
+        if not isinstance(message["content"], str):
+            raise TypeError("Message content must be a string.")  # noqa: TRY003
+
+
+def prompt_tlm_for_rewrite_query(query: str, messages: list[dict[str, Any]], tlm: TLM) -> TLMResponse:
+    """Given the query and message history, prompt the TLM for a response that could possibly be self contained.
+    If the tlm call fails, then the original query is returned.
+    """
+
+    messages_str = ""
+    for message in messages:
+        messages_str += f"{message['role']}: {message['content']}\n"
+
+    response = tlm.prompt(
+        REWRITE_QUERY.format(
+            query=query,
+            messages=messages_str,
+        )
+    )
+
+    if response is None:
+        return TLMResponse(response=query, trustworthiness_score=1.0)
+    return cast(TLMResponse, response)
diff --git a/src/cleanlab_codex/validator.py b/src/cleanlab_codex/validator.py
index c18922f..c4c03a4 100644
--- a/src/cleanlab_codex/validator.py
+++ b/src/cleanlab_codex/validator.py
@@ -7,19 +7,21 @@
 from copy import deepcopy
 from typing import TYPE_CHECKING, Any, Callable, Optional, cast
 
-from cleanlab_tlm import TrustworthyRAG
+from cleanlab_tlm import TLM, TrustworthyRAG
 from pydantic import BaseModel, Field, field_validator
 
 from cleanlab_codex.internal.validator import (
+    REWRITE_QUERY_TRUSTWORTHINESS_THRESHOLD,
     get_default_evaluations,
+    get_default_tlm_config,
     get_default_trustworthyrag_config,
 )
 from cleanlab_codex.internal.validator import (
     process_score_metadata as _process_score_metadata,
 )
-from cleanlab_codex.internal.validator import (
-    update_scores_based_on_thresholds as _update_scores_based_on_thresholds,
-)
+from cleanlab_codex.internal.validator import prompt_tlm_for_rewrite_query as _prompt_tlm_for_rewrite_query
+from cleanlab_codex.internal.validator import update_scores_based_on_thresholds as _update_scores_based_on_thresholds
+from cleanlab_codex.internal.validator import validate_messages as _validate_messages
 from cleanlab_codex.project import Project
 
 if TYPE_CHECKING:
@@ -32,6 +34,7 @@ def __init__(
         codex_access_key: str,
         tlm_api_key: Optional[str] = None,
         trustworthy_rag_config: Optional[dict[str, Any]] = None,
+        tlm_config: Optional[dict[str, Any]] = None,
         bad_response_thresholds: Optional[dict[str, float]] = None,
     ):
         """Real-time detection and remediation of bad responses in RAG applications, powered by Cleanlab's TrustworthyRAG and Codex.
@@ -74,11 +77,20 @@ def __init__(
             ValueError: If any threshold value is not between 0 and 1.
         """
         trustworthy_rag_config = trustworthy_rag_config or get_default_trustworthyrag_config()
+        tlm_config = tlm_config or get_default_tlm_config()
+        self._tlm: Optional[TLM] = None
+
         if tlm_api_key is not None and "api_key" in trustworthy_rag_config:
             error_msg = "Cannot specify both tlm_api_key and api_key in trustworthy_rag_config"
             raise ValueError(error_msg)
         if tlm_api_key is not None:
             trustworthy_rag_config["api_key"] = tlm_api_key
+            if "api_key" not in tlm_config:
+                tlm_config["api_key"] = tlm_api_key
+            else:
+                error_msg = "Cannot specify both tlm_api_key and api_key in tlm_config"
+                raise ValueError(error_msg)
+            self._tlm = TLM(**tlm_config)
 
         self._project: Project = Project.from_access_key(access_key=codex_access_key)
 
@@ -108,6 +120,7 @@ def validate(
         query: str,
         context: str,
         response: str,
+        messages: Optional[list[dict[str, Any]]] = None,
         prompt: Optional[str] = None,
         form_prompt: Optional[Callable[[str, str], str]] = None,
         metadata: Optional[dict[str, Any]] = None,
@@ -129,6 +142,10 @@ def validate(
                 - 'is_bad_response': True if the response is flagged as potentially bad, False otherwise. When True, a Codex lookup is performed, which logs this query into the Codex Project for SMEs to answer.
                 - Additional keys from a [`ThresholdedTrustworthyRAGScore`](/codex/api/python/types.validator/#class-thresholdedtrustworthyragscore) dictionary: each corresponds to a [TrustworthyRAG](/tlm/api/python/utils.rag/#class-trustworthyrag) evaluation metric, and points to the score for this evaluation as well as a boolean `is_bad` flagging whether the score falls below the corresponding threshold.
         """
+        _validate_messages(messages)
+        if messages is not None:
+            query = self._maybe_rewrite_query(query=query, messages=messages)
+
         scores, is_bad_response = self.detect(
             query=query, context=context, response=response, prompt=prompt, form_prompt=form_prompt
         )
@@ -154,6 +171,7 @@ async def validate_async(
         query: str,
         context: str,
         response: str,
+        messages: Optional[list[dict[str, Any]]] = None,
         prompt: Optional[str] = None,
         form_prompt: Optional[Callable[[str, str], str]] = None,
         metadata: Optional[dict[str, Any]] = None,
@@ -175,6 +193,10 @@ async def validate_async(
                 - 'is_bad_response': True if the response is flagged as potentially bad, False otherwise. When True, a Codex lookup is performed, which logs this query into the Codex Project for SMEs to answer.
                 - Additional keys from a [`ThresholdedTrustworthyRAGScore`](/codex/api/python/types.validator/#class-thresholdedtrustworthyragscore) dictionary: each corresponds to a [TrustworthyRAG](/tlm/api/python/utils.rag/#class-trustworthyrag) evaluation metric, and points to the score for this evaluation as well as a boolean `is_bad` flagging whether the score falls below the corresponding threshold.
         """
+        _validate_messages(messages)
+        if messages is not None:
+            query = self._maybe_rewrite_query(query=query, messages=messages)
+
         scores, is_bad_response = await self.detect_async(query, context, response, prompt, form_prompt)
         final_metadata = metadata.copy() if metadata else {}
         if log_results:
@@ -296,6 +318,25 @@ def _remediate(self, *, query: str, metadata: dict[str, Any] | None = None) -> s
         codex_answer, _ = self._project.query(question=query, metadata=metadata)
         return codex_answer
 
+    def _maybe_rewrite_query(self, *, query: str, messages: list[dict[str, Any]]) -> str:
+        """Rewrite the query based on the message history if the query is not a self-contained question but could be improved to be one with context from the messages.
+
+        Args:
+            query (str): The original query.
+            messages (list[dict[str, Any]]): The message history to use for rewriting the query.
+
+        Returns:
+            final_query (str): Either the original query and a rewritten self-contained version of the original query.
+        """
+        if self._tlm is not None:
+            response = _prompt_tlm_for_rewrite_query(query=query, messages=messages, tlm=self._tlm)
+            if (
+                response["trustworthiness_score"] is not None
+                and response["trustworthiness_score"] >= REWRITE_QUERY_TRUSTWORTHINESS_THRESHOLD
+            ):
+                return str(response["response"])
+        return query  # If the trustworthiness score is below the threshold or we don't have access to the TLM, omit the rewrite
+
 
 class BadResponseThresholds(BaseModel):
     """Config for determining if a response is bad.
diff --git a/tests/internal/test_validator.py b/tests/internal/test_validator.py
index 48e6503..13e5986 100644
--- a/tests/internal/test_validator.py
+++ b/tests/internal/test_validator.py
@@ -1,11 +1,15 @@
 from typing import cast
+from unittest.mock import MagicMock
 
+import pytest
 from cleanlab_tlm.utils.rag import TrustworthyRAGScore
 
 from cleanlab_codex.internal.validator import (
     get_default_evaluations,
     process_score_metadata,
+    prompt_tlm_for_rewrite_query,
     update_scores_based_on_thresholds,
+    validate_messages,
 )
 from cleanlab_codex.types.validator import ThresholdedTrustworthyRAGScore
 from cleanlab_codex.validator import BadResponseThresholds
@@ -108,3 +112,40 @@ def test_update_scores_based_on_thresholds() -> None:
     for metric, expected in expected_is_bad.items():
         assert scores[metric]["is_bad"] is expected
     assert all(scores[k]["score"] == raw_scores[k]["score"] for k in raw_scores)
+
+
+def test_prompt_tlm_with_message_history() -> None:
+    messages = [
+        {"role": "user", "content": "What is the capital of France?"},
+        {"role": "assistant", "content": "The capital of France is Paris."},
+    ]
+
+    dummy_tlm = MagicMock()
+    dummy_tlm.prompt.return_value = {
+        "response": "What is the capital of France?",
+        "trustworthiness_score": 0.99,
+    }
+
+    mocked_response = prompt_tlm_for_rewrite_query(query="What is the capital?", messages=messages, tlm=dummy_tlm)
+    dummy_tlm.prompt.assert_called_once()
+
+    assert mocked_response["response"] == "What is the capital of France?"
+    assert mocked_response["trustworthiness_score"] == 0.99
+
+
+def test_validate_messages() -> None:
+    # Valid messages
+    valid_messages = [
+        {"role": "user", "content": "Hello"},
+        {"role": "assistant", "content": "Hi there!"},
+    ]
+    validate_messages(valid_messages)  # Should not raise
+    validate_messages(None)
+    validate_messages()
+
+    # Invalid messages
+    with pytest.raises(TypeError, match="Each message must be a dictionary containing 'role' and 'content' keys."):
+        validate_messages([{"role": "assistant"}])  # Missing 'content'
+
+    with pytest.raises(TypeError, match="Message content must be a string."):
+        validate_messages([{"role": "user", "content": 123}])  # content not string
diff --git a/tests/test_validator.py b/tests/test_validator.py
index 574ed31..f9f09d0 100644
--- a/tests/test_validator.py
+++ b/tests/test_validator.py
@@ -64,6 +64,18 @@ def mock_trustworthy_rag() -> Generator[Mock, None, None]:
         yield mock_class
 
 
+@pytest.fixture
+def mock_tlm() -> Generator[Mock, None, None]:
+    mock = Mock()
+    mock.prompt.return_value = {
+        "response": "rewritten test query",
+        "trustworthiness_score": 0.99,
+    }
+    with patch("cleanlab_codex.validator.TLM") as mock_class:
+        mock_class.return_value = mock
+        yield mock_class
+
+
 def assert_threshold_equal(validator: Validator, eval_name: str, threshold: float) -> None:
     assert validator._bad_response_thresholds.get_threshold(eval_name) == threshold  # noqa: SLF001
 
@@ -109,6 +121,56 @@ def test_validate(self, mock_project: Mock, mock_trustworthy_rag: Mock) -> None:
             assert "score" in result[metric]
             assert "is_bad" in result[metric]
 
+    @pytest.mark.usefixtures("mock_project")
+    def test_validate_with_message_history(self, mock_trustworthy_rag: Mock, mock_tlm: Mock) -> None:
+        validator = Validator(codex_access_key="test")
+
+        result = validator.validate(
+            query="test query",
+            context="test context",
+            response="test response",
+            messages=[
+                {"role": "user", "content": "previous message"},
+                {"role": "assistant", "content": "previous response"},
+            ],
+        )
+
+        # Verify TrustworthyRAG.score was called
+        mock_trustworthy_rag.return_value.score.assert_called_once_with(
+            response="test response",
+            query="test query",
+            context="test context",
+            prompt=None,
+            form_prompt=None,
+        )
+
+        # Verify TLM was called for rewriting query
+        mock_tlm.return_value.prompt.assert_called_once()
+
+        # Verify expected result structure
+        assert result["is_bad_response"] is False
+        assert result["expert_answer"] is None
+
+        eval_metrics = ["trustworthiness", "response_helpfulness"]
+        for metric in eval_metrics:
+            assert metric in result
+            assert "score" in result[metric]
+            assert "is_bad" in result[metric]
+
+    def test_maybe_rewrite_query(self, mock_project: Mock, mock_trustworthy_rag: Mock, mock_tlm: Mock) -> None:  # noqa: ARG002
+        validator = Validator(codex_access_key="test")
+
+        result = validator._maybe_rewrite_query(  # noqa: SLF001 -- intentional test of private method
+            query="confusing test query",
+            messages=[
+                {"role": "user", "content": "previous message"},
+                {"role": "assistant", "content": "previous response"},
+            ],
+        )
+
+        mock_tlm.assert_called_once()
+        assert result == "rewritten test query"
+
     def test_validate_expert_answer(self, mock_project: Mock, mock_trustworthy_rag: Mock) -> None:  # noqa: ARG002
         # Setup mock project query response
         mock_project.from_access_key.return_value.query.return_value = ("expert answer", None)
diff --git a/tests/utils/test_function.py b/tests/utils/test_function.py
index dc4706c..916d697 100644
--- a/tests/utils/test_function.py
+++ b/tests/utils/test_function.py
@@ -23,7 +23,7 @@ def function_without_annotations(a) -> None:  # type: ignore # noqa: ARG001
 
     fn_schema = pydantic_model_from_function("test_function", function_without_annotations)
     assert fn_schema.model_json_schema()["title"] == "test_function"
-    assert fn_schema.model_fields["a"].annotation is Any  # type: ignore[comparison-overlap]
+    assert fn_schema.model_fields["a"].annotation is Any
     assert fn_schema.model_fields["a"].is_required()
     assert fn_schema.model_fields["a"].description is None