I couldn't figure out how to separate out the envelope identity from the email address in the header in alpine (pine). There may not be a way to do this. I set up a workaround in your alpine so that it will use a different role when you send a message to gmail.com. > From: robert <http://dummy.us.eu.org/robert> > Date: Sun, 19 Mar 2023 11:34:24 -0700 > > According to https://support.google.com/mail/answer/81126#authentication , > these checks are randomly imposed. So, you may be able to get through > with it, eventually. > > However, in general, you should change your From: to be http://dummy.us.eu.org/noelleg > when sending to anyone with a gmail account, or use your Supersonic Noelle > role in alpine. >