Stop Joining New Windows Devices to On-Premises Active Directory (AD)

The topic of on-premises Active Directory (AD) domain-joined vs Microsoft Entra joined Windows devices comes up quite often in my conversations with MSPs and IT professionals. The conversation usually goes:

“But there are on-premises file shares which are dependent upon on-premises AD, so we have to join Windows device to on-premises AD.”

This is NOT a true statement. You can have Microsoft Entra joined Windows devices and users can still access on-premises file shares without having to type a password or having to cache credentials which are treasure troves for attackers.

“We tried to solve this problem with Microsoft Entra hybrid joined Windows devices, but it’s been an IT management nightmare for us.”

Please, spare yourself and your team the headache. Microsoft Entra hybrid devices are co-managed, which forces you to maintain and support both on-premises and cloud-based tools simultaneously. This redundancy doesn’t just double your infrastructure overhead—it doubles your troubleshooting time whenever something goes wrong. And something will go wrong!

Here are ten (10) reasons why Microsoft Entra joined Windows devices are the “way” moving forward:

1. VPN-Free Remote Access: Users can log in and access cloud resources from anywhere with an Internet connection. Traditional AD-joined devices often require a VPN to process password changes or update security policies, which can lead to locked accounts or “domain trust relationship” errors for users.
2. Native Passwordless Login: Microsoft Entra joined Windows devices support passwordless login via Windows Hello for Business (biometrics like face or fingerprint scan and a PIN). These device-specific authentication methods are not only more secure, but significantly faster and more convenient for the user than typing complex passwords.
3. True Single Sign-On (SSO): It provides an immediate SSO experience for all Microsoft 365 and integrated SaaS apps. Users sign-in to their Windows device and are automatically authenticated for Microsoft Teams, Outlook, and other apps. The Windows device becomes part of their authentication to Microsoft 365, so there are no additional prompts for credentials, or MFA approval prompts on another device.
4. Faster “Out-of-the-Box” Setup: With Windows Autopilot, users can self-deploy a new Windows device from anywhere, sign-in with their corporate email address, and have the new Windows device automatically configured with all their apps and settings in minutes with little if any involvement from IT support staff.
5. Seamless Access to Legacy Resources: Despite being cloud-native, Microsoft Entra-joined devices can still access on-premises file shares and printers using Cloud Kerberos Trust, providing the same “it just works” feel as a domain-joined PC while on the office network. For remote users, they will still need VPN to provide a network path to the on-premises network, but they won’t have to type an additional set of credentials. You can even integrate VPN with Microsoft Entra, so users never have to type a password at all.
6. Infrastructure Reduction: By moving to the cloud, you can decommission or reduce the footprint of physical servers, including on-premises AD domain controllers, file servers and print servers. This removes the burden of hardware maintenance, patching, and OS licensing for local infrastructure.
7. Zero-Touch Deployment: With Windows Autopilot, IT can ship a new Windows device directly from the vendor to a user. Once the user signs in with their corporate email, Windows Autopilot joins the computer to Microsoft Entra and automatically configures policies, security settings, and applications via Microsoft Intune without IT ever touching the computer.
8. Unified Policy Management: Instead of complex, nested Group Policy Objects (GPOs) that only update when on-network, administrators can use Microsoft Intune cloud management to push configuration and compliance policies over the Internet.
9. Simplified Remote Support: IT support techs don’t have to deal with resetting passwords anymore since users sign in to their Windows device with biometric face or fingerprint scan, or a PIN. IT support techs can remotely lock, wipe, or “Fresh Start” a Windows device through the Microsoft Intune admin portal if it is lost, stolen, or being reassigned to a new employee. They don’t have to spend hours manually re-loading an infected device or setting up for transitioning to a new employee.
10. Dynamic Compliance: With Microsoft Entra joined Windows devices, the device is part of the Zero Trust layered security in Microsoft 365. If the Windows device falls out of compliance (e.g., antivirus or security agents are not enabled), it is automatically blocked from accessing corporate resources until IT remediates the compliance issue.

The bottom line is clinging to on-premises AD join for new Windows devices is tethering your team to an outdated, high-maintenance past. By embracing Microsoft Entra join, you aren’t just modernizing your tech stack; you’re reclaiming your time, slashing your infrastructure overhead, and providing a frictionless “it just works” experience for your users. Stop fighting the “hybrid nightmare” and the limitations of legacy domains. Make the shift to cloud-native management today—your help desk, your security posture, and your sanity will thank you.