[Root] Access is an advice column for IT professionals.
How Can I Resolve Conflicts Between On-Premises AD and Azure AD Integration?
An IT pro asks for advice on troubleshooting synchronization and password issues when integrating on-premises Active Directory with Azure AD.
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Dear [Root] Access,
I've recently taken on the challenge of integrating our on-premises Active Directory with Azure AD as part of our organization's push toward a hybrid cloud environment . While I understand the potential benefits—like single sign-on, better security, and centralized identity management—this integration has been far more complicated than I predicted.
Troubleshooting technical issues between on-premises and cloud environments has been a headache, especially regarding synchronization and password issues. Do you have any tips that might help?
—Untangling a Hybrid AD Mess
Dear Untangling a Hybrid AD Mess,
I am sorry you have issues with your hybrid Active Directory environment. Synchronization issues can be frustrating, especially when they disrupt user access, authentication, or group policies. Here are some key steps to diagnose and resolve the problem.
Assess Your Active Directory Synchronization Solution
First, ask whether your Active Directory synchronization solution needs to be upgraded. For quite a few years, Azure AD Connect was the go-to solution for synchronizing an on-premises Active Directory environment with Azure Active Directory. However, Microsoft recommends using Microsoft Entra Connect V2 instead of Azure AD Connect. In fact, Microsoft retired Azure AD Connect in 2022, though many organizations continue to use it.
Microsoft Entra Connect V2 provides the same basic functionality as Azure AD Connect and is generally considered more secure and reliable than its predecessor. It is worth noting, however, that Microsoft Entra Connect version 2 does not work with Windows Server 2012 R2 and earlier systems. Hence, if you are running a version of Windows that is no longer supported, you will need to update to a newer version before switching to Microsoft Entra Connect version 2.
Consider Microsoft Entra Cloud Sync
If you are already using Microsoft Entra Connect V2 and still having trouble, consider using Microsoft Entra Cloud Sync. Microsoft Entra Cloud Sync is an agent-based system that replaces Microsoft Entra Connect (though the two can be used together). It greatly simplifies synchronizations in complex environments, such as those requiring high availability or environments where you need to synchronize multiple Active Directory forests. Another advantage to using Microsoft Entra Cloud Sync is that it supports synchronization for large groups containing up to 50,000 members.
Clean Up Your Active Directory
While it's important to use synchronization software that Microsoft currently supports, synchronization problems are often tied to the health of your Active Directory environment. As such, cleaning up your Active Directory is a good idea.
To get started, remove any Active Directory users or groups that are no longer needed. Remember, any object you can remove from your Active Directory is one less object that could potentially cause a problem.
While you are at it, verify that every Active Directory user has a unique User Principal Name (UPN). This UPN should match the user's email address.
Check for Missing Active Directory Attributes
I have also occasionally seen synchronization problems caused by missing Active Directory attributes. Suppose a particular attribute is required but has been deleted at some point. In that case, the object may not be synchronized because Windows may consider the Active Directory object damaged or invalid. As such, make sure that commonly used attributes such as DisplayName, Mail, and SAMAccountName are populated.
Use IDFix To Detect and Resolve Problems
The good news is that Microsoft provides a free tool to help you detect and resolve Active Directory health issues that are likely to cause synchronization problems. The tool is called IDFix and is available for download here: https://microsoft.github.io/idfix/
IDFix scans your on-premises Active Directory and reports any detected object attribute values that are considered problematic. In some cases, IDFix can correct problems that it detects automatically. In other situations, however, you may need to manually modify the problematic attribute or delete the corresponding Active Directory object.
Final Tip: Run IDFix Multiple Times
If IDFix reports Active Directory errors, fix them and rerun the tool. A single object can have more than one issue. Hence, even if you correct an error associated with an object, additional errors may still exist. You should keep running IDFix until it no longer reports any errors.
More Active Directory-related Tips:
About the Author
Technology Analyst
Brien Posey is a bestselling technology author, a speaker, and a 20X Microsoft MVP. In addition to his ongoing work in IT, Posey has spent the last several years training as a commercial astronaut candidate in preparation to fly on a mission to study polar mesospheric clouds from space.
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