Question

WordPress Marketplace Droplet and Office365 SMTP - StartTLS is needed

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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This question was answered by @Quin452:

Update: no sooner had I posted this, I figured out some changes needed.

I cannot say why WP Mail SMTP didn’t work, but for Post SMTP, I simply had to enable the login details and make sure they were saved properly.

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