Problem with email on non-default SMTP port

Ok. I can’t get email to work with my Discourse install. I’ve got it setup on a DigitalOcean 2gb Droplet and the domain name is on Namecheap. I was able to do the workaround discribed in this post to gain access to finish setup and prep the site, but I still can’t figure out the email controls.

Below I’ve tried to provide as much info as possible for my setup. I’m hoping someone can find the issue so I can move on. Thanks in advance.

Here is my “app.yml” setup:

I run sudo ./launcher rebuild app whenever I change “app.yml”

Here is my Namecheap DNS record: redacted

Here is my DigitalOcean DNS record: redacted

Here is my log file from error when sending test email out of admin panel:

I’m using Namecheap private email for SMTP settings.

I can receive emails to hello(at)peer(dot)cafe so I think the Namecheap records are correct. I can run telnet 465 on my DO droplet and am connected. So I’m thinking the problem is either in my “app.yml” file or the DO records. Any thoughts?

I’m ignoring all the DNS stuff because that has nothing to do with connecting to a SMTP server hosted by someone else.

I think setting DISCOURSE_SMTP_ENABLE_START_TLS to false will solve the problem here.

Generally port 465 is TLS (otherwise known as SSL) - it doesn’t require the START_TLS as it’s already TLS.

You would set START_TLS to true if you were using port 26 (yes 26 perhaps 25 as well) with Namecheap’s service.

Also I believe Namecheap’s SMTP server is responding poorly here - it should be bailing out early and causing an error rather than holding the connection open and not responding - causing a “timeout”.

You would see a no peer certificate available or Secure Renegotiation IS NOT supported error, if both the server handled this correctly and there more verbose error logging here.


Thanks for the help. I tried just changing DISCOURSE_SMTP_ENABLE_START_TLS to false and I’m still getting no delivery. I’m going to try switching it to true and changing port to 26 to see if that will work.

Thanks @DeanMarkTaylor You solved my problem.

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