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Old 11 Jan 2017, 09:25 AM   #8
jhollington
Essential Contributor
 
Join Date: Apr 2008
Posts: 371
Strange. What level of FastMail account are you using? Are you using your own domain or a common FastMail domain?

I'm using a legacy Family Enhanced account with my own domain. While I can't speak for what eumx might be doing, I know that when I send a message from my FastMail account as my Gmail address, there's absolutely no sign of FastMail anywhere in the headers, so I can't see where eumx would be picking that up from at all.

I know that some systems — Microsoft Exchange, Outlook, and Gmail in particular, but perhaps eumx as well — will read different headers within the email message, and if the various "FROM" headers don't match, you get this "Sent on behalf of" situation where it discloses the "real" address used to send the message (also known as the "envelope" address). However, I've just tested all of this in my setup, sending test messages from my FastMail account, via my Gmail account, to other services like iCloud and Hotmail, and then examine the actual raw headers, and I don't see my own domain anywhere in the headers.

That said, if you're using a fastmail.fm domain or similar, the behaviour might be different than using your own domain name. However, regardless of this, I really don't see why the new interface should behave in any way differently from the classic interface in that regard, as this would seem to be more of a back-end thing.... I wouldn't think the web UI would normally have anything to do with what headers are being set.

Are you using the Gmail identity you configured in the "Personalities" section of the classic interface settings or did you configure it under "Identities & Fetch" in the new interface? That might make a different, particularly with Gmail since the new UI actually uses full Gmail authentication and therefore might configure things differently to line up with the new interface, whereas on the classic interface you have to specify all of your settings manually.

Further, if you configured manually in the classic interface and you're not using Gmail's SMTP server to send your outbound messages, it's very possible that this may be part of the issue, since in this case eumx would be receiving a message from a "gmail.com" address from servers that aren't authorized to send for gmail.com. Best practice is to always configure your personality/identity settings to use the provider's own SMTP server. Setting up a Gmail identity in the new interface does this automatically.
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