MAX_RETRIES = 2

def extract_with_retry(document: str) -> Transaction:
    history = [
        {"role": "system", "content": "Extract the transaction details."},
        {"role": "user", "content": document},
    ]
    for attempt in range(MAX_RETRIES + 1):
        completion = client.beta.chat.completions.parse(
            model="gpt-4o", messages=history, response_format=Transaction
        )
        raw = completion.choices[0].message.content
        try:
            return Transaction.model_validate_json(raw)
        except ValidationError as e:
            if attempt == MAX_RETRIES:
                raise  # give up, let the caller route this to a human
            logger.warning("validation failed on attempt %d: %s", attempt, e)
            history += [
                {"role": "assistant", "content": raw},
                {"role": "user", "content": f"That failed validation: {e}. Fix only the bad field."},
            ]