My instance had the same problem, the problem was that Hetzner (where I host my server) by default is not permitting outbound smtp ports. For me the solution was to use alternative port and even that a starttls alternative port which AWS SES luckily supports (that is what I am using for smtp server). Alternative would be also to just ask Hetzner to unblock the port (people have reported success with this method).

following… similar question!

Hi there! Going to take a minute to read through your post, as I banged my head against a the SMTP setup wall for several hours.

Edit ah, ansible, not Docker. Could still be the same issue though. Look in your lemmy backend instance logs for any timeout errors. If you see any, it means your lemmy backend can’t make any outgoing calls and you need to fix that.

But while I do that, assuming you are using the docker method, did you add a secondary external network to the lemmy container in docker-compose.yml? Your email setup looks fine, but without adding the secondary external network your lemmy instance can’t make outgoing calls (federation won’t work either).

Make sure you can connect from your server to ensure firewall rules, passwords, and SSL type are accurate.

openssl s_client -connect smtp.fastmail.com:465 -tls smtp

More directions here as you need to encode your username and password to login from the shell: https://www.stevenrombauts.be/2018/12/test-smtp-with-telnet-or-openssl/

You can replace postfix:25 with smtp.fastmail.com:465 in the config. Verify that you need tls and not starttls as the ssl type.

If this is docker then you need to ensure the container can route to their server and port. I don’t use docker so I can’t help you there but I think it’s something about internal vs external bridge.

Similar, I’m assuming gmail is a no go? I feel like theoretically it should work but it’s not. However, this may be because I’m using elest.io -> docker, but something’s fucked up with my domain’s SSL and it’s signed by itself. It gives the browser a big huge 'ol unsecured warning, so I would assume that because that’s messed up it’s causing gmail to not accept it? I’ve opened a ticket with them, so eventually maybe I can figure out if that’s the case, I’ve never had a problem pointing namecheap domains to anything before.

It says this, but I assure you, the password is correct.

lemmy_server::api_routes_websocket: email_send_failed: permanent error (535): 5.7.8 Username and Password not accepted. Learn more at5.7.8  https://support.google.com/mail/?p=BadCredentials [long chain of numbers and letters I'm not sure matter] - gsmtp

The settings

  # Email sending configuration. All options except login/password are mandatory
  email: {
    # Hostname and port of the smtp server
    smtp_server: "smtp.gmail.com:587"
    smtp_login: "crystals.rest.lm@gmail.com"
    smtp_password: "[the password]"
    # Address to send emails from, eg "noreply@your-instance.com"
    smtp_from_address: "crystals.rest.lm@gmail.com"
    # Whether or not smtp connections should use tls. Can be none, tls, or starttls
    tls_type: "tls"
  }

I also did start stattls and that didn’t work. Tried swapping ports around, nope.

edit: fixed the ssl issue with elest.io, they just had a configuration wrong, but tbf lemmy support was added literally yesterday

second edit: I just didn’t use gmail and instead made a zoho mail account that worked out after a lot of setting up

Mine works fine sending to my SMTP TLS port.

Are you hosting your instance in a cloud provider? Some may block outgoing SMTP ports as a spam-prevention measure. Other instance admins have reported Digital Ocean as one of those providers.