connection time out

[alaaaz]

I am encountering an issue with my Proxmox Mail Gateway setup.

Issue Description:Both incoming and outgoing emails are getting stuck in the queue on our PMG. Despite proper configuration, emails are not being forwarded as expected.

Network Setup:

• Two Exchange servers located behind the firewall:
  • 1st Exchange server: [IP Address 1]
  • 2nd Exchange server: [IP Address 2]
• Proxmox Mail Gateway located in the DMZ: [IP Address 3]
• External relay used for communication: [IP Address 4] (Port 25)

those are outgoing mails

Feb 15 11:16:16 Proxmix postfix/error[193716]: 06128701273: to=<externalmail@externalemail.test>, relay=none, delay=0.05, delays=0.05/0/0/0, dsn=4.4.1, status=deferred (delivery temporarily suspended: connect to ip4[ip4]:25: Connection timed out)
Feb 15 11:16:16 Proxmix postfix/error[193716]: 06128701273: to=<externalmail@externalemail.test>, relay=none, delay=0.06, delays=0.05/0/0/0, dsn=4.4.1, status=deferred (delivery temporarily suspended: connect to ip4up4]:25: Connection timed out)
Feb 15 11:16:16 Proxmix postfix/error[193716]: 06128701273: to=<externalmail@externalemail.test>, relay=none, delay=0.06, delays=0.05/0/0/0, dsn=4.4.1, status=deferred (delivery temporarily suspended: connect to ip4[ip4]:25: Connection timed out)
Feb 15 11:16:16 Proxmix postfix/error[193716]: 06128701273: to=<externalmail@externalemail.test>, relay=none, delay=0.06, delays=0.05/0/0/0, dsn=4.4.1, status=deferred (delivery temporarily suspended: connect to ip4[ip4]:25: Connection timed out)
Feb 15 11:16:16 Proxmix pmg-smtp-filter[193732]: 70127765CDC84FE6526: processing time: 0.131 seconds (0, 0.05, 0)
Feb 15 11:16:16 Proxmix postfix/lmtp[193737]: BABAB701274: to=<externalmail@externalemail.test>, relay=127.0.0.1[127.0.0.1]:10023, delay=0.32, delays=0.12/0.01/0.04/0.14, dsn=2.5.0, status=sent (250 2.5.0 OK (70127765CDC84FE6526))
Feb 15 11:16:16 Proxmix postfix/error[193716]: 06128701273: to=<externalemail@externalemail.test>, relay=none, delay=0.06, delays=0.05/0/0/0, dsn=4.4.1, status=deferred (delivery temporarily suspended: connect to ip4[ip4]:25: Connection timed out)
those are incoming mails
Feb 15 11:19:51 Proxmix postfix/lmtp[193711]: 7A14970126D: to=<test@mydomain.com>, relay=127.0.0.1[127.0.0.1]:10024, delay=302, delays=2.2/0/0.04/300, dsn=2.5.0, status=sent (250 2.5.0 OK (70127265CDC7FBA0D59))
Feb 15 11:19:51 Proxmix postfix/qmgr[193619]: 7A14970126D: removed
Feb 15 11:19:56 Proxmix postfix/smtp[193913]: C928970123D: to=<test@mydomain.com>, relay=ip1[ip1]:25, delay=5.1, delays=0.06/0.02/0.05/5, dsn=4.4.2, status=deferred (lost connection with ip1[ip1] while sending MAIL FROM)
2024-02-15T11:28:32.456088+03:00 Proxmix postfix/qmgr[193619]: C928970123D: from=<test@mydomain.com>, size=5308, nrcpt=1 (queue active)
2024-02-15T11:28:37.557624+03:00 Proxmix postfix/smtp[194079]: C928970123D: to=<test@mydomain.com>, relay=ip2[ip2]:25, delay=526, delays=521/0.03/0.06/5, dsn=5.7.57, status=bounced (host ip2[ip2] said: 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM (in reply to MAIL FROM command))

Despite checking network configurations, firewall settings.
can anyone help me with solving this problem ?

 

[Stoiko Ivanov]

(delivery temporarily suspended: connect to ip4[ip4]:25: Connection timed out)
those are incoming mails

This line tells you that PMG could not connect to ip4 on port 25 - either there is an error in the IP Address or a firewall policy allowing this connection is missing or the host at ip4 does not listen on port 25 (and is not an SMTP server)

2024-02-15T11:28:37.557624+03:00 Proxmix postfix/smtp[194079]: C928970123D: to=<test@mydomain.com>, relay=ip2[ip2]:25, delay=526, delays=521/0.03/0.06/5, dsn=5.7.57, status=bounced (host ip2[ip2] said: 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM (in reply to MAIL FROM command))

This line tells you that the server at ip2 expects everybody sending through it to authenticate with SMTP-AUTH - PMG is meant to be used as a Proxy between the internet and your downstream server - and thus does not have support for outbound SMTP-AUTH
https://pmg.proxmox.com/pmg-docs/pmg-admin-guide.html#chapter_deployment

I hope this helps!