Try this:
set the FLASK_DEBUG environment variable to 1 and then restart your systemd services / docker containers.
Then go to
https://your-instance.tld/test_email?email=your-email%40whatever.com
If it fails is there anything interesting in the logs?
Try removing the MAIL_USE_TLS=True from your .env file. Often SMTP providers will let you use two ports, one of them for TLS and one without. You'll need to try both ports, with MAIL_USE_TLS on and off to eliminate all possibilities.