TIL that the `requests` library supports automatic retries with exponential backoff

You can use a customized Adapter and force several retries with an exponential backoff factor on all HTTP/HTTPS requests. See example below:

import requests
from requests import adapters
from urllib3.util import Retry

# Create a transport adapter with a custom retry strategy.
retries = Retry(
    total=3,
    backoff_factor=3,
    status_forcelist=[500, 502, 503, 504]
)
adapter = adapters.HTTPAdapter(max_retries=retries)

# Ensure adapter is used for both HTTP and HTTPS requests.
session = requests.Session()
session.mount('https://', adapter)
session.mount('http://', adapter)

# Testing the retry mechanism
response = session.get("http://httpbin.org/status/500")

This returns the error below:

RetryError: HTTPConnectionPool(host='httpbin.org', port=80): Max retries exceeded with url: /status/500 (Caused by ResponseError('too many 500 error responses'))

The unfortunate thing is that there doesn't seem to be a way to tell how many times the above mechanism has attempted to retry, only when all attempts have been exhausted

Reference

https://stackoverflow.com/a/47475019/4477547