Microsoft has been putting a lot of upgrades into Outlook.com – its free mail service. A recent update now has many of us using outlook.com at a business-class email experience.
Updated 1-26-2017 – this tip applies to people who use Outlook 2016/2013 on Windows only. If you have a Mac, you don’t need this tip.
The process of upgrading these accounts somehow disconnects or degrades the connection between outlook.com and the desktop Outlook 2016/2013. Microsoft has sent emails out on how to reconnect to Outlook 2016/2013 to continue with uninterrupted mail delivery to your desktop Outlook.
I first got a notice in the summer, but I was just too busy with a number of projects to look at it. I got another one this week and decided to take care of it.
Do You Have The Outlook.com Upgrade?
If you got an email from Microsoft, that means that account has been upgraded. I have several Outlook.com accounts and when I went to read about this upgrade, the blog post said they have upgraded ALL Outlook accounts – that means if you have a .hotmail, .live or .msn account, they have been or will be upgraded.
Here’s the link to the Microsoft article on how to reconnect Outlook 2016 or 2013.
How do you know if you’ve been upgraded? Luckily, there is an easy way. Just log into your Microsoft email account and if you have a search box that says, “Search Mail and People”, you are upgraded. Here are two of my accounts and it is easy to see which is which.
How To Reconnect Your Outlook.com to Desktop Outlook
There are three ways to do the reconnect – they are:
- If you only have one Outlook.com email on your desktop application.
- If you have more than one email running on your desktop application.
- Work-arounds for known issues (custom domain, outlook crashes, outlook appears with a long string of numbers).
Reconnect to Outlook – Only 1 Email Account on Desktop Outlook
Note: You do not need to delete the old profile first and can refer to it to get the new one set up. Once you have the new profile set up, you should select to “Always use this profile” option, or delete the old profile.
- Go to Control Panel
- Search for Mail
- Choose Show Profiles,
- Then Add – choose a name, then click OK
- Now, it’s time to set up the new Outlook account. You can do it from this screen and click on Email Accounts and add it right there, or you can do as Microsoft suggests and open your desktop Outlook and go to File>Add and add your account there.
- You should only need to fill in your name, email address and password and Outlook should find all the settings for you.
Reconnect to Outlook – More Than 1 Email Account on Desktop Outlook
I tried this way to see if it would work, but it would not connect to the server. The email account I was trying to update was a custom domain, so I needed to go to the Work-Around method. Here are the steps if you have a ‘regular’ Outlook account.
- Open Outlook.
- On the File tab, under Account Information, choose Account Settings > Account Settings.
- On the E-mail tab, select the email account you want to remove, and then choose Remove on the mini toolbar
- Now go through the steps listed above to add your account by filling in your name, email address and password and you should be all set!
Remove your current, or old Outlook account here 
Reconnect to Outlook – 3 Known Issues
Microsoft has listed 3 of their top known issues which are detailed at the beginning of this article.
I’m going to talk about the issue I had – which was since I had a custom domain, I was having problems reconnecting. For the last several months, I’ve noticed my mail has been extremely slow to pop in on my desktop Outlook, but it was always there when I checked it from the web. I didn’t put two and two together until I got the second reminder email this week – duuhhh.
If you’re wondering what a custom domain is, let me explain. For a number of years, Microsoft had a little-known perk where they’d let anyone configure a personally-branded custom domain. I blogged about this in 2013 and set up two accounts. Several years later, Microsoft took that nice perk away and they said everyone who had a custom domain could keep it for free, for the time being.
Back to the instructions…
To fix my problem, I logged into my domain registrar (I use Hover), and took a look at my MX records. There I saw a MX entry with the term ‘invalid’ in there. I figured that had to be wrong and I deleted that record. Now Microsoft didn’t address that at all, their fix is to add a CNAME record to the DNS settings. But I thought first I’d try removing this invalid record and then try to set my account up and wa-la, it worked.
I decided to try reconnecting to Outlook without adding a CNAME record and things are working well, so for now, I will leave it as is. After I took out the invalid MX record, it all worked for me.
The Other Two Known Issues
They are Outlook crashing and Outlook showing up in your email account with an extremely long name.
Since I didn’t face either of these, I’ll leave you with this link for the troubleshooting fixes for those.
If you haven’t logged into your Outlook email account for a while, you may be greeted with this image after your account is upgraded. I signed into a little-used Outlook account and found it was upgraded with this message. There’s a series of images and even some video to tell about the changes. Enjoy!
