setting up outlook.com custom domain account in Outlook client fails

pandafusion
pandafusion used Ask the Experts™
on
Windows 10
Outlook 2010 32 bit version 14.0.7162.5000
(Also fails in Outlook 2013, Nine app for Android, etc.)

I have an outlook.com account that uses a custom domain name. You could get that a couple of years ago. It has been working fine ever since.

I received an email informing me:

"In the next few weeks we’ll be making some updates that will impact your @outlook.com, @hotmail, @live, or @msn email account. Those changes will prevent your email from getting delivered to the Outlook desktop application you use. When you notice that you stop receiving messages, simply follow these two steps: "

Sure enough, my email account (user @ mydomain.com) stopped working in Outlook 2010. I can log on to the web interface using my credentials, so I know my credentials are correct.

I removed my account in Outlook 2010 successfully. However, I have not been able to successfully add the account using the linked instructions here:
https://support.office.com/en-us/article/Add-your-Outlook-com-account-to-Outlook-2010-6636e88f-3d21-413b-9fd1-38a99dfcb199?ui=en-US&rs=en-US&ad=US

When adding the account, I get the error message:

"An encrypted connection to your mail server is not available.

Click next to attempt using an unencrypted connection"

That also fails. Various other messages indicate I am using the incorrect password (though the password works fine when logging into the web client).

I appreciate any help. This is starting to really cost me time and money. Maximum points for a correct answer. I am also having trouble configuring the account using the outlook app - which tells me my credentials are wrong.

Thank you.
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Muhammad BurhanManager I.T.
Top Expert 2015

Commented:
give a try with SSL enable/disable.
Hi,

To add your Outlook.com account with Outlook 2010, the very first point is you must install Microsoft Outlook Hotmail Connector according to bit version of Outlook.

Like for 64-bit version use 64-bit version and for 32-bit version of Outlook use 32-bit version.

Regards
Most Valuable Expert 2015
Distinguished Expert 2018
Commented:
Actually, the connector will not longer work once your account is migrated to the new platform. You need to remove the account from Outlook then add it back as Exchange account. Diane has a short guide here: http://www.slipstick.com/outlook/outlookcom/first-look-outlook-com-on-office-365/

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Commented:
Vasil:

Thank you for the article. That is the first bright spot I have seen :)
Please see Mark's comments on November 22 for a thread relating to my issue. It appears Diane is having a similar issue. She indicates this is a known Microsoft issue and they are working on it, with no current ETA.

I can confirm the following:
The migration is on a per-account basis, not a per-domain basis. I currently have an account (user1@mydomain.com) that has been migrated (URL is outlook.live.com) and an account (user2@mydomain.com) that has not been migrated (URL is bay169.mail.live.com). To confirm, mydomain is the same domain name for both of these accounts. Based on viewing several of these accounts, I believe less active accounts are being migrated first, and highly active accounts will be migrated later.

I have attempted the work-around suggested by Clive for adding an @outlook.com alias to the account. However, I am unable to actually add the alias. Any alias address entered returns the error "(alias address)@outlook.com is not available". To be clear, I have tried obscure email addresses like usermydomainXXXX@outlook.com and various variations on that theme. None of them is working.

Still looking for help implementing a work-around.

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