Microsoft’s forced migration of users from the old Outlook.com infrastructure based on Hotmail to the new one based on Exchange hit me today.

I can no longer send emails from my business address and Outlook 2016 desktop is broken.

This is partly because because the new system is unreliable and partly because Microsoft is going to make using your own domain a premium service.

What does work?

• Any email address like myname@outlook.com that is set to the be account’s primary alias. If it is not the primary alias then Outlook 2016 will turn your name into something like outlook_KDJEIAGEKDJLJSD@outlook.com.

What does not work?

• Many users report that you cannot successfully connect an account. Therefore you can no longer send using a different email address. For example, my business email address is hosted on 1and1 and is james@xxxx.co.uk. Yesterday I could connect Outlook.com to this address and send emails from web Outlook or desktop outlook using that address. Today I cannot.
• Yesterday I could use my alias james@xxxx.co.uk to create an account in Outlook 2016 because I manually set up the ExchangeSync access. Today I cannot. This is because now 1 must use the default method to add Exchange email addresses and I get autodiscovery failure (as I must because Microsoft don’t own the domain’s DNS records). Other users report that even creating your own autodiscovery records does not result in a successful addition of the account.

Options

I have spent the day on this problem and there are no obvious solutions but lots of problems

• Purchase a business essentials account on Office 365
  • This is cheap but would require Office 365 to handle ALL my mail on my business domain. I have lots of addresses for systems so that is not practical

— update 2018/09/25 —

I have now moved to Office 365 Business Premium and implemented a catch all address for my other email address. This is described here.

• Abandon using Outlook.com for email, just use it for calendaring. Connect to my 1and1 host using IMAP
  • I will have a big problem syncing all my data back to 1and1 and might lose it all. I will certainly lose all my Outlook categories.
• Try to use EAS again – eas.outlook.com and see if it works at least until they turn it off (Microsoft says it will corrupt my data they could be lying).

Next Steps

I will see if it all looks better in the morning.

Update 2016-11-13

I worked with Microsoft Support for 2 hours on this and I learnt.

• There was an issue with connected accounts and POP that was fixed in November 2016 (No information is available about IMAP)
• The migration of an account from old Outlook.com (EAS based access) to new Outlook.com can take TWO WEEKS to complete successfully.

RESOLUTION

Wait 48 hours after the migration before trying to connect accounts and then use POP

NOTE

I have also found by experimentation if you use Outlook 2016 Desktop then

• You cannot connect to the new Outlook.com using the alias of your connected account
• If your primary alias is xxxxxxx@outlook.com then you should, after 48 hours, be able to connect to Outlook.com
• If your primary alias is not the outlook.com one then you cannot connect to Outlook.com after 48 hours but might be able to do so after two weeks.

 

Keywords

Outlook.com, Outlook.com migration, connected accounts, pending update, imap, pop, custom domain