Discourse setup on official Digital Ocean droplet not producing emails

I’m using the officially supported installation of Discourse through the official Digital Ocean droplet. I set one site up successfully (jordanviolet.dev) and currently setting up a second site (violetfamily.com).

  • Domain is through Google Domains, but nameservers are on Digital Ocean
  • Both are using their respective domain emails, which are Google Workspace accounts (so @jordanviolet.dev and @violetfamily.com, respectively)
  • Both have 110% identity configurations on Google Workspace, domains, etc. I have checked what feels like two dozen times.

jordanviolet.dev setup great and sent the emails out!

violetfamily.com had an email error, I fixed that by allowing non-secure applications per this guide (which worked for jordanviolet.dev):

It sent out one email, but the registration expired and it hasn’t sent out an email since, though it seems to be getting 200 OK in the logs when I run tail -f shared/standalone/log/rails/production.log and then send the email out—I get this:

Started HEAD "/" for 13.57.1.58 at 2024-05-18 18:39:43 +0000
Processing by FinishInstallationController#index as */*
  Rendered finish_installation/index.html.erb within layouts/finish_installation (Duration: 0.9ms | Allocations: 187)
  Rendered layout layouts/finish_installation.html.erb (Duration: 23.7ms | Allocations: 2771)
Completed 200 OK in 61ms (Views: 25.3ms | ActiveRecord: 0.0ms | Allocations: 8607)
Started GET "/" for 13.57.1.58 at 2024-05-18 18:39:43 +0000
Processing by FinishInstallationController#index as */*
  Rendered finish_installation/index.html.erb within layouts/finish_installation (Duration: 0.6ms | Allocations: 187)
  Rendered layout layouts/finish_installation.html.erb (Duration: 9.4ms | Allocations: 2575)
Completed 200 OK in 14ms (Views: 10.5ms | ActiveRecord: 0.0ms | Allocations: 3736)

I receive no emails. Any suggestions? I feel I’ve exhausted my options at the moment.

EDIT:

After sitting still for a while and not making changes, one oddly came through but with a timestamp of about 10 minutes old (and also then the link to confirm my email was expired).

I wonder if something is just stuck in the smtp relay somewhere, and I just need to wait it out.

It seems that Google will soon be deprecating less secure apps from being possible with their platform for email:

Will have to do some research to see if there are any Discourse guides currently for setting up a new install with Google email using OAuth.

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For anyone else who comes across this, what finally worked for me (though not understandably so):

Disabling and reenabling my MX servers seems to have done the trick.

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