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I'm trying to configure my Gmail account so that I can use it to send mail as my Microsoft address (let's say it's example@hotmail.com), but I'm getting a weird error.

I've already gone into Gmail's Settings > Accounts and Import and added the Hotmail address under the "Send mail as" section, using server smtp.live.com, on port 587 with TLS. Gmail is now asking me to verify that I own the Hotmail address via an e-mailed code.

Unfortunately, every automatic verification mail that Gmail sends to example@hotmail.com results in this:

Delivery to the following recipient failed permanently:

    example@hotmail.com

Technical details of permanent failure:
Google tried to deliver your message, but it was rejected by the server for the recipient domain hotmail.com by mx4.hotmail.com. [65.55.92.184].

The error that the other server returned was:
550 Requested action not taken: mailbox unavailable

----- Message suppressed -----

The exact Hotmail server varies but the message is otherwise the same.

Some quick searching shows that a 550 error usually results when an e-mail address is entirely invalid, as would happen if the account didn't exist. However, I can log into Hotmail as example@hotmail.com and when I manually type up an e-mail in Gmail and send it to example@hotmail.com, it goes through just fine.

What can I do to finish setting up this mail alias?

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    If I'm not mistaken, the SMTP server is smtp-mail.outlook.com not hotmail. – Braiam Dec 4 '15 at 6:06
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Well, I don't know why Gmail wants to send a test message to anyone, the only thing I had to do to prove myself the owner of the account was to provide the correct password. If you followed http://windows.microsoft.com/en-us/windows/outlook/send-receive-from-app, and set up the smpt as smtp-mail.outlook.com, and can send mails using the "From" selector, I wouldn't worry about the failed "test".

  • example@hotmail.com isn't the actual address. I just didn't want to post the actual address in the question. – Pops Dec 4 '15 at 8:39
  • Separately from the previous comment, sending mail does not work. Gmail won't let me send mail until I prove (to Google, at least) that I own the Hotmail account by passing its test. While I was writing the first half of this comment though, I restarted the whole procedure using the alternate SMTP server you mentioned in the comment under the question, and setup was successful, so if you update the answer I'll accept. – Pops Dec 4 '15 at 8:47
  • @Pops I set up my account yesterday (before writing this answer) and Gmail didn't asked me for a test email. I wrote what you said was the problem, but I would recommend also verifying the POP/IMAP configurations too and make sure they are as the guide says. – Braiam Dec 4 '15 at 15:21

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