Remote Desktop Access to Microsoft Entra ID Joined Device

All content and design elements on this website are the exclusive property of Josh Fridey and are protected by United States copyright and intellectual property laws. Unauthorized use, reproduction, or distribution of any material without prior written permission is strictly prohibited and may result in civil or criminal penalties.

This website includes third-party code, assets, or open-source libraries used under their respective licenses.

Remote Desktop Protocol (RDP) is an essential tool for IT professionals and end users alike, allowing seamless remote management and access to multiple devices. However, with the transition to Microsoft Entra ID (formerly Azure Active Directory), the traditional process of accessing remote devices has changed slightly, introducing a few additional steps.

In this guide, I’ll share my preferred method for accessing Microsoft Entra ID-joined devices via RDP. Keep in mind that there are multiple ways to accomplish this, some potentially easier. However, this method works effectively for both onsite and offsite configurations.

Prerequisites

To ensure a successful remote connection, you’ll need the following:

• VPN Connection if wanting off-site access.

Configuring the Remote Device (The device you want to access)

1. Set a Static Local IP Address

   1. This helps maintain a consistent connection and prevents address changes from affecting access.

2. Enable Remote Desktop Protocol (RDP)

   1. Go to Settings > System > Remote Desktop and enable Remote Desktop.

3. Network Level Authentication (NLA), recommended enabled. Keep this checked for security. If you are having trouble connecting and suspect NLA is the blocker, you can temporarily disable it to test.

   1. Open System Properties › Remote.
   2. Under Remote Desktop, uncheck Allow connections only from computers running Remote Desktop with Network Level Authentication (NLA).
   3. Try the connection again. If it works, address the root cause, then re-enable NLA.

Configuring the Local Device (The device you’re accessing from)

1. (For Offsite Access) Connect to VPN

   1. Ensure you’re connected to your organization’s VPN before proceeding.

2. Modify the Host File

   1. Open Notepad as Administrator
   2. Navigate to C:\Windows\System32\drivers\etc\hosts
   3. Add the static IP address and exact computer name of the remote device to the file.
   4. Note: The computer name must be exact, as Microsoft Entra ID requires an exact match for authentication.

3. Launch the Remote Desktop Application

   1. Open the Remote Desktop app and enter the host name of your remote device.
   2. Important: IP addresses will not work with this method; you must use the computer name.

4. Enter Login Credentials

   1. Username: Enter your Microsoft 365 email address
   2. Navigate to the Advanced tab > User Authentication section
   3. Check the box for “Use a web account to sign into the remote computer”

Conclusion

By following these steps, you can successfully remote into a Microsoft Entra ID joined device using RDP. This method ensures compatibility with both onsite and offsite (with VPN) setups, allowing seamless access across different environments.