So, I’ve migrated a site into a DO droplet, and everything seems fine, for the most part.
Except, whenever I try to send an email via the Office365 mail servers, I get the error message of “StartTLS is needed” using the Post SMTP plugin. I have tried WP Mail SMTP as well, but that just kicked out a lot of numbers (I cannot understand that).
Ports 25 and 587 are open, and I can even send emails from the droplet myself via CLI, but these need to be routed through Office365 and I’m not sure what needs fixing.
Once I rewewed the certs using certbot, it gave me a link to check the TLS, and it says I am ready for 1.3.
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