My email is hosted by GoDaddy and the servers are smtpout.secureserver.net and pop.secureserver.net.
Gmail re-writes the from: field when I use an invalid email address, putting the original into X-Google-Original-From:
Does GoDaddy do that?
Is this a free GoDaddy account? I don’t think the free accounts allow you configure an email alias at all?
Right, so your ISP has nothing to do with it - you are just using them as a conduit to connect to Godaddy.
It’s not about comparing Reply-To and From as much as it is noticing that the email did not actually originate from the server where the From: line says.
Personally, I’d expect the only way to reliably do what the OP wants would be to actually set up the address to be able to send mail, and then log into that account when you need to send things. That is how I pull it off with multiple accounts on Gmail.
Also, FYI, Outlook.com will freak if you send more than one email from the same address in a short period of time. That’s how dumb spam filters can be.
That would be nice but it’s not possible for reasons described upthread. The hosting contract does not include email without a significant extra charge that our HOA does not think is worth paying.
I don’t know why I didn’t think of this before–I have my own web site with a mailing list, and it includes PHP code for the admin (me) to send email to the list. It’s a small list, a dozen or so. I can put anything I want for From and Reply To. I could gin up a page to do this for the HOA.