Discourse Email does not work after fresh installation (Zoho SMTP server)

After a fresh install of Discourse on a new Ramnode server following these instructions, I am trying to configure the email to interact properly with a Zoho email client. So far, I have not been able to send any emails using Discourse. I’ve already checked out this page: https://meta.discourse.org/t/cannot-get-email-to-send-using-zoho-mail/45554/4.

When I test my smtp server using swaks, an email is sent properly:

swaks --to me@example.com --from do-not-reply@sfhepbfree-bayarea.org --server smtp.zoho.com --auth LOGIN --auth-user do-not-reply@sfhepbfree-bayarea.org -tls -p 587.

This leads me to believe there is an issue with Discourse. Using the following settings:

DISCOURSE_SMTP_ADDRESS: smtp.zoho.com DISCOURSE_SMTP_PORT: 587 DISCOURSE_SMTP_AUTHENTICATION: "login" DISCOURSE_SMTP_USER_NAME: do-not-reply@sfhepbfree-bayarea.org DISCOURSE_SMTP_PASSWORD: "..." DISCOURSE_SMTP_ENABLE_START_TLS: true # (optional, default true)

I have received the following error:

530 Must issue a STARTTLS command first.

What settings are possible for the DISCOURSE_SMTP_ variables? Why would email work with swaks but not through Discourse?

I don’t have any ideas. You might run ./discourse-doctor and see if its mail debug tester sheds any light.

Zoho won’t work for bulk emails. It’s against their policies.

Use mailgun or something similar instead.

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That error is from the ./discourse-doctor

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Can you point to where in their policies they forbid bulk emails? They just seem to have a strict anti-spam policy…

Anyway, I don’t believe that to be the cause of the technical problem…

I just recommended a less painful option for You. If you absolutely gotta have zoho to send emails, try contacting their support as they are the ones who can help with the error code. The recommended email providers do work well for discourse and I don’t see anywhere in the documentation where discourse recommends zoho or google apps for business to send emails.

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And did you rebuild after you made those settings?

Does the host name of your forum match what the mail server is configured for?

I did rebuild. And I decided to give elasticemail a try. Now, with elasticemail, I have the rather intriguing problem that email works when test emails are sent with ./discourse-doctor (they arrive in my inbox, receive a 10/10 score at mailtester, etc), but I am not receiving the activation emails when trying to register for the admin account. The logs only say:

Started POST "/finish-installation/register" for 136.152.143.124 at 2018-08-20 22:58:06 +0000 Processing by FinishInstallationController#register as HTML Parameters: {"utf8"=>"✓", "authenticity_token"=>"S9k3wSRqJ2/M+JNLbWNMu8S8YJ/+0KyaRI+CGbxRxWrzNkfhhT/Fz8+G+hn/DnKl3jSxIYd+mkZf2MqdIW1Z0Q==", "email"=>"pinkardmichael@gmail.com", "username"=>"mpinkard", "password"=>"[FILTERED]", "commit"=>"Register"} Redirected to https://forum.sfhepbfree.org/finish-installation/confirm-email Completed 302 Found in 11ms (ActiveRecord: 1.0ms) Started GET "/finish-installation/confirm-email" for 136.152.143.124 at 2018-08-20 22:58:06 +0000 Processing by FinishInstallationController#confirm_email as HTML Rendering finish_installation/confirm_email.html.erb within layouts/finish_installation Rendered finish_installation/confirm_email.html.erb within layouts/finish_installation (2.0ms) Rendered common/_special_font_face.html.erb (0.5ms) Rendered layouts/_head.html.erb (0.3ms) Completed 200 OK in 7ms (Views: 4.8ms | ActiveRecord: 0.0ms)

However, the email is not being logged in elasticemail at all. Any ideas?

I think I’ve seen a problem before where if the first attempt at sending the registration email fails it’s hard to get Discourse to try again.

Try going to /login and doing forgot password.

Nice! That worked! Thanks so much!

That information should perhaps be added to the email troubleshooting page?

Well, I think it’s more of a bug/UX issue that I’ve reported here: Wizard will not send validation email more than once.

@gerhard, did you have a chance to take a look?

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