Python - Optimal way to check for a condition with a timeout?

Wrote two functions, 1. uploads a gzip file to Artifactory and 2. listens to the Kafka topic. As further steps, wanted to validate whether the upload is successful within 5 minutes by listening to the Kafka topic for the keyword - push_status: True, else fail the script. I'm kind of stumped with the logic that is more elegant and pythonic on the else part.

Code snippet:

upload_status = fetch_kafka_topic("topic", "brokers") #Returns messages from particular topic.

if bool(upload_status) == True: #Checks if the returned dictionary is empty or not
    if upload_status['file_sha'] == EXPECTED_SHA: # CHeck if the SHA Values  matches with the one I've in prior.
        if upload_status['push_status'] == True:
            print("upload is successful ...")
        else:
            Monitor and query the kafka topic again for the keyword for 5 mins and fail the build if it exceeds the timeout.

Is this the case?

from datetime import datetime, timedelta


def query_upload_success():
    upload_success = False
    upload_status = fetch_kafka_topic("topic", "brokers")
    if bool(upload_status) == False:
        return upload_success
    is_successful = (upload_status['file_sha'] == EXPECTED_SHA and upload_status['push_status'] == True)
    if is_successful:
        upload_success = True
        print("upload is successful ...")
    return upload_success


def timed_query_upload():
    start_time = datetime.now()
    stop_time = start_time + timedelta(minutes=5)
    while True:
        upload_success = query_upload_success()
        if upload_success:
            break
        start_time = datetime.now()
        if start_time > stop_time:
            print("exceeds the timeout ...")
            break

if __name__ == '__main__':
    timed_query_upload()