In November 2015, Microsoft announced changes to their Outlook.com services that will impact your ability to send/receive emails if you’re using any email account @hotmail, @live, @msn, @outlook.com. They have also provided a guide on how to fix the problem if, at some point, you stop receiving emails to your Office Outlook email client.

While working on other unrelated issues, I had the opportunity to also work on this particular case, where emails suddenly stopped being delivered to the Outlook desktop application.

Although they were all fixed just by following Microsoft’s guide, there was one instance where it did not work, and I had to find a solution on my own.

This was the scenario: PC running Windows XP PRO, MS Outlook 2003 with Outlook Connector. This machine used to sync 2 @hotmail.com and 2 @msn.com accounts, but after the “Latest and Greatest” Microsoft upgrade to Outlook.com none of them were working.

Here I am going to detail a solution, should you incur in a similar situation. Basically, the difference between Microsoft’s suggested guide (that didn’t work) and my guide (that works) is on the IMAP and SMTP settings. Microsoft indicates to use the following:
imap-mail.live.com
smtp-mail.live.com
but it didn’t work for me. I used imap-mail.outlook.com, smtp-mail.outlook.com.

Anyhow, let’s go step-by-step.

First, you must remove the email account that’s not working from your Outlook. Go to Tools > Email Accounts… > View or change existing email accounts, select the email account you want to remove and click on the “Remove” button, click Finish. Exit Outlook.

Log in to your web-based account by pointing your browser to outlook.com, or hotmail.com, live.com. Once you’re logged in, click on the upper right “gear” icon,

then click on Options. Under Mail,
select POP and Imap. Tick Yes Under POP options (Let devices and apps use POP).

The next two options, you’ll have to decide which one to choose, based on your needs. If you don’t know, here’s an explanation of what they mean:

Don’t allow devices and apps delete messages from Outlook on the web. It will move the messages to a special POP folder instead. By selecting this, when you delete a message from your application (in this example, Outlook 2003), your message is not actually deleted from your mailbox. Instead, it is moved to an automatically created folder named POP, waiting for you to bring it back to life or delete it permanently.

Let apps and devices delete messages from Outlook on the web. If you select this, deleting a message from your app it will permanently delete it. Don’t look for it on outlook.com because it won’t be there.

So, make your choice and click on the Save icon at the top of the page.

Now leave the cloud and come back to earth, on your PC, open Outlook, click on Tools > E-mail Accounts… > Add a new e-mail account > Next.

Add a new e-mail account.

Select IMAP

On the following screen, select IMAP and click Next.

Next screen, enter your account details. For the purpose of this guide, I have named my email account my_name@hotmail.com.

Incoming mail server (IMAP):
imap-mail.outlook.com

Outgoing mail server (SMTP):
smtp-mail.outlook.com

Click on More Settings…

General tab, type in your name or whatever you like,
Outgoing Server tab, check My outgoing server (SMTP) requires authentication,

My outgoing server (SMTP) requires authentication

Advanced tab, select both Incoming server (IMAP): Port 993 This server requires an encrypted connection (SSL)
and Outgoing server (SMTP): Port 25 This server requires an encrypted connection (SSL).

Click OK.

Your email account is now listed in Outlook, along with any other accounts you might have.

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