Hi guys,

I've been running OpenSMTPD for a long time now forwarding mail to my
gmail account. It's a pretty basic rig - there are just a series of
forwarding rules, and different @somedomain.com emails get forwarded
to different @gmail.com emails.  I have DKIM, SPF, and even DMARC all
set up correctly. Outgoing emails that an authorized user on the MTA
sends are DKIM signed. Forwarding emails aren't, which is the correct
behavior.

It turns out this all is a lot harder than I initially thought. Gmail
often blocks spam at the SMTP level. My server tries to deliver to my
gmail account a piece of spam email, gmail's SMTP servers say "no way
josé here's error 502", and then my server generates a bounce email.
This bounce email contains the spam contents of the email that was
initially sent, meaning now my server is sending spam across the
Internet! My fix for this was to patch [1] OpenSMTPD not to include
the body of the email, but rather only the headers. This prevents my
IP from being blacklisted _too_ quickly. But still, bounce messages
are sent, and sometimes my IP does get banned by an organization I
send email to, and I have to apply for whitelisting and it's a
tremendous PITA. The other issue is that Google is now in the habit of
replying "you're forwarding spam; don't do that; bye" to my server,
and it doesn't know that my server is just forwarding the message. As
such, my IP's reputation with Google is steadily becoming horrible
over time.

Is there a good one-stop fix for this? The whole reason I'm still
using Gmail is because I like its spam filter! I certainly don't want
to run an additional spam filter on my OpenSMTPD machine. Are there
other configuration things I can do to make the situation better?

Thanks,
Jason



[1] https://bpaste.net/show/fbcc2134cfda

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