Hi everyone,
We're currently migrating approximately 3,000 Windows endpoints from traditional Active Directory to Microsoft Entra Join, with Intune and Microsoft Global Secure Access (GSA / Entra Private Access).
One challenge we're facing is how to preserve effective remote troubleshooting capabilities for our L2/L3 support technicians and IT analysts.
Our current environment
With AD-joined devices, we use WinRM / PowerShell Remoting extensively for interactive troubleshooting, diagnostics, inventory queries, and remediation.
For example, a technician can:
- Connect to a remote workstation using PowerShell.
- Query services, processes, registry settings, WMI/CIM, event logs, and Windows configuration.
- Investigate an issue interactively.
- Execute a corrective action.
- Immediately verify the results.
- Continue troubleshooting based on what was discovered.
This is particularly valuable because troubleshooting is rarely a predefined sequence of actions.
The challenge with Entra Join and GSA
We understand that WinRM can work with Entra-joined devices under certain conditions.
However, using WinRM through GSA, especially for remote endpoints without direct network connectivity, appears to be considerably more complicated.
Our architects are understandably cautious about maintaining traditional remote administration capabilities in a modern Zero Trust environment.
But here's my concern: What about the technicians and analysts who actually troubleshoot workstations every day?
Why Intune Remediations may not be enough
Intune Remediations are useful for proactive management, automated corrections, and recurring issues.
However, they don't necessarily replace interactive troubleshooting.
Consider a technician investigating a Windows service issue.
With WinRM, they can query the service, inspect dependencies, examine logs, test a hypothesis, apply a correction, and immediately verify the outcome.
With Intune, the process may involve creating or selecting a remediation script, deploying it, waiting for execution, retrieving results, and repeating the process if additional investigation is required.
Furthermore, our L2/L3 technicians and analysts won't necessarily have access to Intune administrative functions, nor should they require broad Intune permissions simply to diagnose a workstation.
We don't want every troubleshooting operation to depend on an Intune administrator or someone developing a new remediation script.
My questions to the community
- How are you handling interactive remote troubleshooting for L2/L3 technicians in an Entra-joined environment?
- Have you successfully retained WinRM / PowerShell Remoting, including for remote endpoints using GSA?
- If you've moved away from WinRM, what solution replaced its interactive diagnostic capabilities?
- How do your technicians retrieve diagnostic information and execute corrective actions without having to create and deploy new scripts for every investigation?
- Has your organization implemented a solution that provides immediate, interactive PowerShell diagnostics while respecting Zero Trust and least-privilege principles?
I'm not opposed to modernization or replacing WinRM.
If a modern solution provides equivalent or better functionality with appropriate security controls, I'm all for it.
But I believe we need to distinguish endpoint management from interactive technical support.
Replacing a technology should not mean losing operational capabilities that support teams rely on daily.
I'd be particularly interested in hearing from organizations managing thousands of Windows endpoints that have already completed this transition.
What does your L2/L3 troubleshooting workflow actually look like today?