Hey all, I'm having a lot of trouble trying to get OctoText SMTP settings to work on OctoPrint running inside a jail on a TrueNAS server. I used this amazing guide to set up the octoprint server and it works flawlessly, however when trying to use the OctoText plugin it doesn't want to cooperate.
I tried making both gmail and outlook accounts, I tested using SMTP Test Tool and both accounts worked using TLS, google also worked using SSL with respective ports. I also tried using the "app passwords" for google multifactor authentication accounts, which worked in gmass testing but not for OctoText.
I also tried to telnet to smtp.google.com from the shell of the TrueNAS jail and it let me do it so I'm assuming that connectivity isn't the issue.
TrueNAS jail setup!