Score:-1

Server

What could be causing PowerMTA not to forward emails over port 465 SSL...?

Sabrina sage

6/4/24, 9:56 PM

We have a PowerMTA server that receives incoming e-mail. and forward it to external SMTP server that's not running PowerMTA i tried to do it using port 587 and port 25 both working fine and emails forwarded successfully but with port 465 its not working

173

1 + 9

linux

ssl

smtp

centos

certificate-authority

anx

6/4/24, 11:01 PM

Relaying to many different SMTP servers does not inspire confidence in reasonable practices.. Do you have a User Manual for the software you are using? What does it say on the topic?

joeqwerty

6/5/24, 12:10 AM

Just because your server is listening on port 465 doesn't mean that the remote server is listening on port 465, which it probably isn't.

Jaromanda X

6/5/24, 12:45 AM

`i tried to connecte with port 465` was this to `external-smtp-server.com`? `using OpenSSL` in what way did you "use" OpenSSL for this

Jaromanda X

6/5/24, 12:51 AM

is [this](https://stackoverflow.com/questions/76388589/what-could-be-causing-powermta-not-to-forward-emails-over-port-465-ssl) you as well, or did both you and that user sign up on the same day and ask the same question with the same config in two different stack exchange sites?

Steffen Ullrich

6/5/24, 5:17 AM

*"i tried to connecte with port 465 using OpenSSL and its working fine"* - could you add more detail on what you were doing, specifically: did you try **from** the same host where PowerMTA is running **to** the same target host port 465 as PowerMTA should use? Because ETIMEDOUT suggests that there is some firewall blocking the connection to the target host, in which case openssl should not work either from the same source to the same destination.

Sabrina sage

6/5/24, 10:37 AM

@anx All SMTPs are our SMTPs we preferred to connect with it using Powermta just because they offer too many features that will help as improve your quality of deliverability

Sabrina sage

6/5/24, 10:39 AM

@jaromanda-x conneting with OpenSSL was in same server of Powermta i tried this just to make sure that my server allow outbound connection using port 465 and we connected with same SMTP i used in Powermta (External SMTP)

Sabrina sage

6/5/24, 10:43 AM

@jaromanda-x yes both are me but as i see here serverfault is much better as I got many engagements from many great members in stackoverflow i got no answer

Sabrina sage

6/5/24, 10:46 AM

@steffen-ullrich yes that the exact problem tha openSSL allow me to connecte to same SMTP using same port and from same host where powermta running but with OpenSLL email sent successfully and in Powermta i got error i think there is problem with Powermta Config thats why i hade no success

Score:1

Server

HBruijn

6/5/24, 7:08 AM

SMTPS on port 465 for use by MTA's quickly became a legacy protocol and evolutionary dead-end, abandoned already in the 1990's in favour of the STARTTLS mechanism on default SMTP port 25 and appears to simply not be supported by PowerMTA.

For securely sending e-mail PowerMTA appears to only support STARTTLS.

The SMTPS protocol is supported by PowerMTA, but only as the secure submission port for clients and not for the MTA:

<smtp-listener 127.0.0.1:465>
  immediate-tls true
</smtp-listener>

+ 5

Sabrina sage

6/5/24, 10:52 AM

Oh got you So there is no way to use Port 465 on "smtp-hosts " inside VMTA to route emails to an external SMTP ? or maybe any other method inside Powermta we can use to forward emails to port 465 of an external SMTP

Steffen Ullrich

6/5/24, 10:59 AM

This explains the *"ETIMEDOUT while connecting - Connection closed by the remote host port"*: the client is waiting for the SMTP servers plain text welcome message before sending anything, while the server is waiting for the client to start with the TLS handshake before sending anything.

HBruijn

6/5/24, 11:06 AM

Indeed. Powermta doesn't recognise port 465 as intended for smtps, won't spontaneously initiate a TLS handshake and AFAIK can't be configured to do so either.

Sabrina sage

6/5/24, 11:09 AM

@HBruijn so in this situation there is nothing to do to fix ??

HBruijn

6/5/24, 11:12 AM

Not server side as the sender. Your recipients need to properly support current standards i.e. STARTTLS on port 25 and/or the submission port 587. Unless there is undocumented feature in PowerMTA

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