this post was submitted on 25 Jan 2026
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As the topic would suggest I've run into another problem with PieFed...I have Mailgun set up as my SMTP host for password resets and the like, the password to my knowledge is correct as I've tested the configuration out in a separate Python script and it logged into smtp.mailgun.org successfully on port 587.

Has anyone else set up Mailgun or similar external SMTP hosting that may be able to help debug the issue?

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[–] rimu@piefed.social 3 points 2 days ago* (last edited 2 days ago) (1 children)

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.

[–] Phoenix1@piefed.social 1 points 2 days ago (1 children)

Thank you, I tried this from my Docker version of the instance, mail seems to be sent as normal through that...I just need to figure out why it's happening with the non-Docker version, so I'll have to test that and check the logs once I get a chance. It's probably something in the "hard way" configuration that I didn't get right along the way!

[–] wjs018@piefed.wjs018.xyz 4 points 2 days ago (1 children)

If you are trying to run things on a VPS, many hosting companies will block the standard email ports by default to prevent spammers from using their network. Usually you have to go through some extra steps to open up those ports.

Some smtp services will allow you to use a nonstandard port. I use resend.com to send smtp emails, and this is what my PieFed environment variables look like:

MAIL_USE_TLS=True
MAIL_SERVER='smtp.resend.com'
MAIL_PORT=2587
MAIL_USERNAME='resend'
MAIL_PASSWORD='my_api_key'
MAIL_FROM='my_from_email@instance.tld'
[–] Phoenix1@piefed.social 1 points 2 days ago

Ah, my configuration looks very similar, the only difference is that I'm using Mailgun 😁 I am self-hosting and our IP does allow HTTP/HTTPS, but not SMTP for obvious reasons!