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My mail.office365.com aka outlook.office.com account has asked me to reconnected my mail.live.com account. This is what I have tried.

9:24 am at mail.office365.com...

  1. Clicked Settings > Mail > Connected accounts > New
  2. Added my mail.live.com email (foobar@outlook.com) and password.
  3. Clicked OK.

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The result says

Unsecured connection: A secured connection couldn't be established to this account. Not all providers offer secured connects. Click OK to try an unsecured connection. Click Skip to configure your account settings.

9:25 am at mail.live.com...

foobar@outlook.com inbox receives an email from the Microsoft account team, which cues me to "Review recent activity." I can see that activity but have no other action for me to take.

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9:32 am at mail.office365.com...

  1. Clicked OK to try an unsecured connection.
  2. Microsoft tells me, "We couldn't connect to the server for you other account..." and cues to me to choose either POP or IMAP.
  3. I try with both IMAP and POP.

IMAP failed with this message:

A test connection to that account wasn't successful. Either the email address or password that you typed isn't correct.

POP failed with this message:

Couldn't log on to the specified mail server because either the username or password was rejected.

I have verified that POP is enabled at my outlook.com account and have double checked my POP and IMAP settings.

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I am at a loss of what to do, because I know that both the email and password are correct.

My best guess is that this has something to do with the "Unusual activity" in my foobar@outlook.com account, and that I somehow have to allow this sign in attempt. That is, the unusual sign-in activity email said:

To regain access, you'll need to confirm that the recent activity was yours.

How do I confirm that the recent activity was mine?

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I faced the same problem with my accounts. Now solved...

You have 2 accounts: 1st = main and 2nd = to be connected. Go to 2nd account settings (web) > activate POP

Go to 1st account > start connection of 2nd account Step 1: user name and password > it will fail and will be able to click Skip to provide some additional settings Step 2: provide all required settings, incl. pop server and SSL flag > click to Connect > it will check your settings and fail with this message "... rejected" > do NOT click "Back"

It's the problem: Go to 2nd account > check your mails > in inbox or junk you will have a mail like "... bad activity" with URL to activities page > click on it

(you will need probably to provide a confirmation code and so on)

Solution: 2nd account > On activities page you have to click "It's me" > like confirm that the (last) activity is OK! 1st account > now, click "Back" and without any changes click on "Connect" again > it will be able finally to verify your account and connect your 2nd account to 1st!

PS: I personally spend 2 evenings solving it and called support that was absolutely not able to help me.

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