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I guess I need to get serious about finding a solution to this problem of my mail to gmail users being rejected because of my laptop VPN IP -- even though the mail is actually delivered by an upstream SMTP server that gmail has no issue with.

@johns wow, how does gmail know your client IP? Shouldn't your SMTP server hide it?

@tahnu Actually looks like I was wrong about the example this morning -- it *was* just gmail rejecting my upstream SMTP server. But I have had issues with them looking into the prior headers in the past.

@johns
Yes, mailservers looking into received headers they should ignore is a thing, I added some config to strip the received headers from fsf.org email because of you. I don't want to do it universally for fencepost email, but I should setup an option. Touch ~/more-private-email ? Then you can send through fencepost for your personal domain. You weren't into that happening, but I think it is fine and good! Obviously, this is post-LibrePlanet.

@johns I just found out that at least in spamassassin from trisquel 11 with the latest ruleset downloaded, it will do checks on all the received headers beyond your defined internal network. So I just made fencepost strip all received headers for mail submitted to it.

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