On Wed, Oct 20, 2021 at 02:57:27PM -0400, Dan Ziolkowski wrote:

> Oct 20 14:28:17 xxxx-OptiPlex-990 postfix/smtp[2522]: 2DA852E306A:
> to=<x...@gmail.com>, relay=none, delay=20, delays=0.13/0.02/20/0,
> dsn=4.4.3, status=deferred (Host or domain name not found.
> Name service error for name=smtp.gmail.com type=AAAA:
> Host not found, try again)

Well, there you are.  With the VPN on your DNS no longer works to
resolve the A and/or AAAA records of smtp.google.com.  You need to make
sure that /etc/resolv.conf contains at least one nameserver IP address
that continues to work when the VPN is up.

> VPN off
> 
> Oct 20 14:31:50 xxxx-OptiPlex-990 postfix/smtp[13019]: 8CDEC2E306E:
> to=<x...@gmail.com>, relay=smtp.gmail.com[173.194.208.109]:587, delay=1.8,
> delays=0.09/0.02/0.73/0.97, dsn=2.0.0, status=sent
> (250 2.0.0 OK 1634754710 128sm1354479qkl.111 - gsmtp)

And now the IPv4 address resolves.  You may be unlucky enought to be
using systemd-resolved, in which case... good luck!

-- 
    Viktor.

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