Hello PythonAnywhere folks,
There are several providers out there which offer a service known as transactional email. It means they act as a third party for sending out email - see table comparison at socialcompare
It seems the selling point of these solutions is the ability to gather statistics about what recipients click in messages, but as I see it, it can also be used as a middle man for sending out mails for low-volume websites (when outbound SMTP is blocked like in PA).
Apparently all of them provide some sort of REST API on top of SMTP, with a daily usage cap to prevent abuse. There are several Python libraries which seem to provide a more convenient interface to those APIs, such as python-mailsnake or more specific ones like django_email_multibackend, django-mandrill, or djrill which integrate as an EMAIL_BACKEND for Django.
Do you think you could add a couple of those sites to the whitelist? I personally would not mind if you set a limit on message size in the proxy configuration, since most delivered mails are either email confirmation, error reporting, notifications etc. messages and do not require a large body.
Thanks for your attention