Issues with sending initial verification email on DigitalOcean

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DigitalOcean Email Verification Issue

A user, jennjenn, encountered issues with sending the initial verification email on DigitalOcean while installing Discourse. The problem was caused by setting up the app.yml file using an IP address as the host instead of a domain, resulting in the notification email being sent from noreply@IPaddress, which was blocked by DigitalOcean or Mandrill.

To resolve the issue, jennjenn suggested:

  • Creating a second admin account through the CLI
  • Changing the notification email to a non-IP-based email account in the Discourse admin panel
  • Regenerating the verification email for the original account

codinghorror recommended blocking the bootstrap process if an IP address is set as the mailing address or adding a warning comment in app.yml and the cloud install documentation. codinghorror updated the email troubleshooting guide to cover this scenario, thanking jennjenn for the feedback.

1

This is less of an issue and more of a summary of what I just spent the last 2 hours trying to debug - hopefully it’ll save you some time!

I followed the instructions to a T for installing Discourse on DO. Booted it up and tried to set up my admin account. Fail. The verification email never went through. I went through alllllll of the troubleshooting documentation and eventually contacted DO support to see if I was being blocked somehow. Nothing.

If your emails aren’t going thru on DO (via Mandrill specifically, not sure if this is true for others):

If you set up your app.yml using an IP as your host instead of a domain, that’s the root of your issue. The notification email is coming from noreply@IPaddress which DigitalOcean or Mandrill or someone in between views as no bueno.

  • Set up a second admin account thru the CLI
  • Log into Discourse and go to the admin panel.
  • Change your notification email to a non-IP-based email account (preferably the one you have connected with Mandrill)
  • Save that
  • Log out of your second account and regenerate the verification email for that first account.
  • Success

Hope that helps!

2

Others have discovered this as well. We should block bootstrap if an IP address is set up as the mailing address, or at least put a comment to that effect in app.yml and the cloud install doc.

3

For now I updated the email troubleshooting guide to explicitly cover this scenario. Thanks for the feedback, sorry for the frustration.