Okay... I'm on Chapter 4. As far as mail is concerned, everything is working beautifully. Already had relaying set up in IIS and I've done the web.config mail setup on many other sites.

Create new user, password recovery, change password, all the mail goes through fine. EXCEPT...if I set up a user with a Gmail account, no dice. WTF?!?

The mail "sends" successfully. No error messages show up. It's just that the mail never gets to the Gmail account. All other email accounts I've tried receive these mails almost instantaneously.

Why should this be happening? It makes absolutely no sense to me at all!

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I had the same problem when I set up the mail, and it turned out that the mails I sent to my Google account was considered spam by Google, and then placed in the spam folder...

If this is the case, mark the message as not-spam. Worked for me...

Yes, I thought of that, but they are not ending up in the Spam folder either. They are simply not getting to the Gmail mailbox AT ALL. Again, this only seems to happen with Gmail addresses.

Has anyone else seen this issue?