Ubuntu 22.04 LTS - Linode mirrors and image have some issues

I recently decided to upgrade from ubuntu 20.04 to 22.04.
I tried two different ways:
1) Spin up a fresh new instance, and install everything I need
2) Spin an instance from the image of my existing server (20.04), and then upgrade it in place

With both options, my website lost the ability to send emails. It uses Google SMTP-relay and kept throwing error. If someone else has a similar need, please don't upgrade your Linode yet.

I was able to boil down the issue to this simple piece of python code that will throw an error. Anyone who has access to Google's smtp-relay can try this to see what I mean.

import smtplib

fromaddr='your@email.com'
toaddr='your@email.com'

with smtplib.SMTP('smtp-relay.gmail.com', 587,'yourdomain.com') as s:
    s.sendmail(fromaddr, toaddr, 'hello')
    s.quit()

I wasted too much time trying to problem solve this. The above program runs fine in the following instances
1) My existing Linode 20.04
2) My local Ubuntu 22.04, upgraded in place from 20.04
3) My local Ubuntu 22.04, fresh installation
4) Ubuntu 22.04 on AWS