Add Outlook.com to Microsoft Outlook - Step-by-Step Guide

Adding Outlook.com Accounts to the Outlook Desktop Application
The desktop version of Microsoft Outlook is compatible with email addresses from Outlook.com, specifically those concluding with @outlook.com, @hotmail.com, @live.com, and @msn.com.
The method for incorporating these accounts isn't always straightforward, particularly when two-step verification is enabled.
Supported Outlook Versions
This guide utilizes Outlook 2016 for demonstration purposes.
However, the outlined procedure remains consistent across Outlook 2013 and current iterations of Outlook 2010 as well.
Users of more recent Outlook versions will find the steps identical.
Successfully adding your Outlook.com account allows centralized email management within the Microsoft Outlook application.
Adding an Outlook.com Email to Outlook
Despite being signed into Windows 10 using a Microsoft account, Outlook doesn't automatically recognize and offer to incorporate that account. The built-in Mail app within Windows 10 is the only application capable of automatically logging in with your Outlook.com email address linked to your Microsoft account.
To integrate an Outlook.com email address into Microsoft Outlook, it must be added as a separate email account. Begin by launching the Outlook application on your computer.
Navigate to the "File" menu, located in the upper-left corner of the Outlook window.

Within the Info pane, select the "Add Account" button, found under Account Information, to initiate the process of adding your email account.

On the Add Account screen, input your Outlook.com email address and corresponding password into the designated "Email Address" and "Password" fields.
Also, specify your name in the "Your Name" field; this name will accompany all outgoing emails sent through Microsoft Outlook.

Provided the login credentials are accurate, Outlook should swiftly establish a network connection and automatically retrieve the necessary settings for your @outlook.com, @hotmail.com, @live.com, or @msn.com address. Successful configuration will be indicated by a message confirming the account is ready for use.
Should a "Problem Connecting to Server" error appear, and you are certain of the password and email address accuracy, consult the troubleshooting steps provided below.

Important Note: While Windows 10's Mail app automatically connects, Outlook requires manual configuration for Outlook.com accounts.
Troubleshooting Connection Issues
If you encounter difficulties, double-check your email address and password for any typos. Ensure your internet connection is stable. Sometimes, a temporary server issue on Microsoft's end can cause connection problems.
Consider enabling two-factor authentication on your Microsoft account, which may require an app password to be generated for use within Outlook. This enhances security.
Resolving the "Problem Connecting to Server" Error with Two-Step Verification
Related: The Importance of Utilizing Two-Factor Authentication (2FA)
Encountering a "Problem Connecting to Server" message often indicates that you have activated two-step verification for your Outlook.com email account.
Microsoft Outlook’s handling of this situation, and its subsequent communication of the issue, is frequently inadequate. The error message often incorrectly states that "an encrypted connection to your mail server is unavailable."
Understanding the Issue
The core of this problem lies in how Outlook interacts with accounts secured by two-step verification. A standard password will not suffice for authentication.
To overcome this connectivity error, generating a dedicated app password specifically for Microsoft Outlook is necessary. While Outlook should ideally guide you through this process, it often fails to do so.
Creating an App Password
Begin by accessing the Microsoft account page using the Outlook.com email address you are attempting to configure. Then, navigate to the "Security & Privacy" section.
If two-step verification is currently enabled on your account, a corresponding message will be displayed: "Your account is protected by two-step verification."
Within this section, locate and click the "Create a new app password" option, found under the "App passwords" heading.
Troubleshooting Alternative Scenarios
Should two-step verification not be activated, the connection issue stems from a different source. Double-check the accuracy of your entered account credentials.
Furthermore, verify a stable Internet connection. Potential problems could involve your internet service, a proxy server configuration, or an active VPN.
Configuring Outlook with the App Password
Re-initiate the account addition process within Microsoft Outlook.
Instead of your regular Outlook.com password, input the newly generated "App password" provided during the previous step.
Verifying Successful Connection
Following these steps, Outlook should establish a successful connection to your Outlook.com account, resolving the error message.
Managing App Passwords
There is no need to record the app password for future reference.
To generate a new app password at any time, revisit the Microsoft account security page and select the "Create a new app password" link.
To revoke existing app passwords, choose "Remove existing app passwords." This will disable access for any applications currently utilizing those passwords until a new password is provided.
Any applications that relied on the removed app passwords will require a new password to function correctly.
Utilizing Your Outlook.com Email Account
Within Outlook, your Outlook.com account will be displayed in the sidebar, alongside any other email accounts you may have integrated.
The synchronization of your emails between Outlook.com and the Microsoft Outlook desktop application is facilitated by the Exchange ActiveSync protocol. Consequently, modifications performed in one location are mirrored in the other. For instance, deleting an email within the Outlook application will also result in its removal from Outlook.com.
Configuration of your account, its removal, or the selection of a default account when managing multiple accounts can be achieved by navigating to File > Info > Account Settings. The necessary options are then available within the Account Settings window.