Outbound SMTP not working on my External Relay

[girish]

@subtlecourage So, the connections are failing with "socket timeout waiting on connect" . Can you SSH into your server and check if "telnet smtp.xxx.com 465" works? If it doesn't , then it could either be the VPS provider is blocking it OR that the smtp provider is blocking it. I tried to connect from my server(s) and it connects fine. So, it's probably a VPS thing. Are you on linode by any chance? I recently learnt they block outbound port 465 and 587 by default on new accounts.

[subtlecourage]

@girish No, I am using hetzner

I am getting a -bash: telnet: command not found

Ok, just kidding.

I installed it.

I got this

:~$ telnet smtp.fastmail.com 465
Trying 66.111.4.140...
Connected to smtp.fastmail.com.
Escape character is '^]'.
Connection closed by foreign host.

[girish]

@subtlecourage Ah ok, so the smtp connection works well enough. Strange then, did you figure this one out already?

[subtlecourage]

@girish said in Outbound SMTP not working on my External Relay:

@subtlecourage Ah ok, so the smtp connection works well enough. Strange then, did you figure this one out already?

Sadly, no.
I keep getting these messages
[outbound] Ongoing connection failed to 66.111.4.140:465 : socket timeout waiting on connect

That is to fastmails servers

Is there any DNS setting that could cause that?

[subtlecourage]

@subtlecourage

I cant get any welcome emails to send, nor password reset emails. This is neutering my install.

[girish]

@subtlecourage Not sure what is going on here. Are you able to contact us on support@cloudron.io, so we can debug on the server?

[girish]

@subtlecourage my bad, I should have noticed. The issue here is that Cloudron's relay system only supports STARTTLS. This means that you have to use port 587 in your relay. Port 465 is pure "TLS" (as opposed to port 587 which is opportunistic TLS). Can you try with port 587? If that doesn't work, let me debug further.

[subtlecourage]

@girish said in Outbound SMTP not working on my External Relay:

@subtlecourage my bad, I should have noticed. The issue here is that Cloudron's relay system only supports STARTTLS. This means that you have to use port 587 in your relay. Port 465 is pure "TLS" (as opposed to port 587 which is opportunistic TLS). Can you try with port 587? If that doesn't work, let me debug further.

Hah, that solved it.

Thank you.

[subtlecourage]

@girish

It is doing something weird though.

It says it should be coming from noreplay@domain.com, but instead it is coming from imanalias@domain.com

Any ideas?

[girish]

@subtlecourage said in Outbound SMTP not working on my External Relay:

It says it should be coming from noreplay@domain.com, but instead it is coming from imanalias@domain.com

Can you clarify what you mean by "it says"? Is there some error/warning somewhere? Also, I assume that you have put a custom domain in fastmail and also fastmail is able to relay mail as any email address i.e <anything>@domain.com ?