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The Microsoft Outlook desktop application supports Outlook.com addresses ending in @outlook.com, @hotmail.com, @live.com, and @msn.com. However, it's not necessarily obvious how to add them--especially if you're using two-step verification.
We used Outlook 2016 for this tutorial, although this same process also works on Outlook 2013 and up-to-date versions of Outlook 2010.
How to Add an Outlook.com Email Address to Outlook
Even if you've signed into Windows 10 with a Microsoft account, Microsoft Outlook won't notice and offer to add that account. Only the much more basic Mail app included with Windows 10 can automatically sign into your the Outlook.com email address associated with your Microsoft account.
To add an Outlook.com email address to Microsoft Outlook, you'll have to add it like any other email account. First, open the Outlook application on your PC.
Click the "File" menu at the top left corner of the Outlook window.
Click the "Add Account" button under Account Information on the Info pane to start adding your email account.
In the Add Account screen that appears, enter your Outlook.com email address and password in the "Email Address" and "Password" fields.
You should also enter your name in the "Your Name" box--this name will be sent attached to any outgoing emails you send from Microsoft Outlook.
Assuming you provided the correct login information, Microsoft Outlook should quickly establish the network connection, get the appropriate settings for your @outlook.com, @hotmail.com, @live.com, or @msn.com address, and log on to the mail server. Outlook will tell you the account was successfully configured and ready to use if you entered the details correctly.
If you see a "Problem Connecting to Server" error and you're sure you typed the correct password and email address, read below for the likely solution.
How to Fix the "Problem Connecting to Server" Error if You have Two-Step Verification
If you see a "Problem Connecting to Server" error, there's a good chance you've set up two-step verification for your Outlook.com email account.
Microsoft Outlook does a very poor job of handling this and informing you of the problem. Instead, it says that "an encrypted connection to your mail server is not available." This just isn't true.
To get past this error, you'll need to generate an app password for Microsoft Outlook. Outlook itself should tell you this, but doesn't.
To create a special password for Outlook, sign into the Microsoft account page with the Outlook.com email address you're trying to add and click "Security & Privacy".
If two-step verification is enabled, you'll see a message saying "Your account is protected by two-step verification." If so, click "Create a new app password" under App passwords.
If two-step verification isn't enabled, there's a different problem with connecting to your Outlook.com account. Be sure you've entered your account details correctly. You should also ensure you can connect to the Internet properly--there may be a problem with your Internet connection, proxy server, or VPN.
Go through the account-adding process in Microsoft Outlook again, providing the "App password" shown here instead of your actual Outlook.com password.
Outlook should now connect to the Outlook.com account properly, with no errors.
You don't need to write down the app password. Instead, if you ever want to create a new app password, head to the Microsoft account security page and click the "Create a new app password" link.
To erase any existing app passwords, click "Remove existing app passwords" here. Any applications you signed into with app passwords will then stop working until you provide a new app password.
How to Use Your Outlook.com Account
Your Outlook.com account will appear alongside any other email accounts you've added in Outlook's sidebar.
Microsoft Outlook uses the Exchange ActiveSync protocol to synchronize your emails with Outlook.com. This means that any changes you make in the Outlook desktop application will also be made in Outlook.com. For example, if you delete an email in Outlook, it'll also be deleted on Outlook.com.
To configure your account, remove it, or choose your default email account if you have multiple accounts in Outlook, head to File > Info > Account Settings and use the options in the Account Settings window.
