Thanks to Bernard Reino for explaining why these two vpn problems are different. Here's a new thread.
OK, so once again, here's the issue. Mail works when the vpn is off, but does not work when the vpn is on. I have two personal servers I run for two different groups, one with exim and one with postfix. I use ProtonVPN and Mullvad as VPNs on my laptop. When I have either vpn running, mail works fine through my exim box and hangs sending to my postfix box. I'm running kubuntu on my laptop: $uname -a Linux n1 5.11.0-37-generic #41-Ubuntu SMP Mon Sep 20 16:39:20 UTC 2021 x86_64 x86_64 x86_64 GNU/Linux I use evolution as my mail client on the laptop. Here's the interaction with the vpn off (sending mail from fp...@libertyfp.org to fp...@libertyfp.org) using a Verizon hotspot: Oct 20 21:16:57 libertyfp postfix/smtpd[175562]: connect from 87.sub- 174-212-171.myvzw.com[174.212.171.87] Oct 20 21:16:59 libertyfp postfix/smtpd[175562]: F0DEF3FFFD: client=87.sub-174-212-171.myvzw.com[174.212.171.87], sasl_method=LOGIN, sasl_username=fp...@libertyfp.org Oct 20 21:17:00 libertyfp postfix/cleanup[175572]: F0DEF3FFFD: message- id=<19099fae22427a89ced6cf0e764d13749e7c9326.ca...@libertyfp.org> Oct 20 21:17:00 libertyfp opendkim[919]: F0DEF3FFFD: DKIM-Signature field added (s=mail, d=libertyfp.org) Oct 20 21:17:00 libertyfp postfix/qmgr[1542]: F0DEF3FFFD: from=<fp...@libertyfp.org>, size=557, nrcpt=1 (queue active) Oct 20 21:17:00 libertyfp dovecot: lmtp(175574): Connect from local Oct 20 21:17:00 libertyfp dovecot: lmtp(fp...@libertyfp.org)<175574><MiDXJyxrcGHWrQIAHPmxyw>: msgid=<19099fae22427a89ced6cf0e764d13749e7c9326.ca...@libertyfp.org>: saved mail to INBOX Oct 20 21:17:00 libertyfp postfix/lmtp[175573]: F0DEF3FFFD: to=<fp...@libertyfp.org>, relay=mail.libertyfp.org[private/dovecot- lmtp], delay=0.99, delays=0.87/0.08/0.03/0.02, dsn=2.0.0, status=sent (250 2.0.0 <fp...@libertyfp.org> MiDXJyxrcGHWrQIAHPmxyw Saved) Oct 20 21:17:00 libertyfp postfix/qmgr[1542]: F0DEF3FFFD: removed Oct 20 21:17:00 libertyfp dovecot: lmtp(175574): Disconnect from local: Client has quit the connection (state=READY) Oct 20 21:17:00 libertyfp postfix/smtpd[175562]: disconnect from 87.sub-174-212-171.myvzw.com[174.212.171.87] ehlo=2 starttls=1 auth=1 mail=1 rcpt=1 data=1 quit=1 commands=8 Here's the log from where the vpn is on: Oct 20 20:07:49 libertyfp postfix/smtpd[174025]: warning: hostname ip245.tervelnet.com does not resolve to address 87.246.7.245 Oct 20 20:07:49 libertyfp postfix/smtpd[174025]: connect from unknown[87.246.7.245] Oct 20 20:07:51 libertyfp postfix/smtpd[174025]: warning: unknown[87.246.7.245]: SASL LOGIN authentication failed: UGFzc3dvcmQ6 Oct 20 20:07:51 libertyfp postfix/smtpd[174025]: disconnect from unknown[87.246.7.245] ehlo=1 auth=0/1 rset=1 quit=1 commands=3/4 Oct 20 20:09:35 libertyfp postfix/smtpd[174449]: warning: hostname ip245.tervelnet.com does not resolve to address 87.246.7.245 Oct 20 20:09:35 libertyfp postfix/smtpd[174449]: connect from unknown[87.246.7.245] Oct 20 20:09:37 libertyfp postfix/smtpd[174449]: warning: unknown[87.246.7.245]: SASL LOGIN authentication failed: UGFzc3dvcmQ6 Oct 20 20:09:37 libertyfp postfix/smtpd[174449]: disconnect from unknown[87.246.7.245] ehlo=1 auth=0/1 rset=1 quit=1 commands=3/4 87.246.7.245 is the address the vpn is using (in Bulgaria) and a web utility like "whatismyipaddress.com" resolves it to ip245.tervelnet.com However, nslookup and dig on my laptop do not resolve it: %nslookup ip245.tervelnet.com Server: 127.0.0.53 Address: 127.0.0.53#53 ** server can't find ip245.tervelnet.com: NXDOMAIN > server 8.8.8.8 Default server: 8.8.8.8 Address: 8.8.8.8#53 > ip245.tervelnet.com Server: 8.8.8.8 Address: 8.8.8.8#53 ** server can't find ip245.tervelnet.com: NXDOMAIN Any help would be appreciated.