The format of my secrets file is:

my_relay sender:PASSWORD

Any strange glyph to be concerned about?

At one point I was trying to connect to the server with openssl and when I used
perl -MMIME::Base64 -e 'print encode_base64("SomeBase64Code");' " for my
password it was truncating because of a char, so I changed that password out but
it made no difference.

Can you authenticate with openssl?

Ok, lets rethink this. Assuming it stopped working the moment the system got rebooted. Than there once was a working configuration, that can be recreated. But if it stopped working around the time of the reboot there is the possibility the provider changed something, making it incompatible with OpenSMTPD. (Than it would be nice to have real hostnames.)

You could try:

action "relay" relay host smtps:// auth <secrets>

action "relay" relay host smtp+tls://

(I assume you use smtpd only to send system message to your personal inbox on So maybe sending to someone on the system doesn't require authentication.)

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