[pkamb]

The worst is their abysmal "On Behalf of:" handling when sending as an @gmail.com address from another @gmail.com address. There is no way around having your "main" email end up in plaintext in the header of every email you send as the "anonymous" email. And anyone replying to you via Outlook replies to the main address. You can send as @yahoo or @hotmail addresses with no evidence of your main gmail account, but for some reason they don't let you with a second gmail address.

[gabemart]

Where does this "On Behalf of:" text appear? I just tested this, and sending an "on behalf of" email to another gmail account doesn't result in this text appearing anywhere in the gmail client. The original mail address appears in the headers under "Sender:" with the alias mail address appearing under "From:". However, if you open the email in gmail and don't check the headers manually, there's no indication it's not from the alias address. Replying to such an email, the "To:" field populates properly with the alias address.

[krakensden]

I have a client company who uses exchange, it generates that line, instead of the more old school

On Oct 99, 2012, at 3:33 PM, KrakensDen yawped:

[pkamb]

In gmail, you'll be able to see the person's "secret" main email address in the `Sender:` field after clicking `Show Original`.

The real annoyance is Outlook. If someone responds to that email via Outlook/Exchange, the reply will be sent `To:` your main email address rather than to the address you sent with.