Troubleshooting Exchange 2010 Management Tools startup issues

🛠️ Exchange 2019 CU15 to Exchange Server SE on Windows Server 2025: Setup and Troubleshooting Summary

As part of a deployment initiative, I began building a new Exchange Server environment—starting with Exchange 2019 CU15 on a fresh Windows Server 2025 platform, then transitioning to Exchange Server SE. Here's an updated summary of the configuration path and detailed troubleshooting steps I’ve taken during this process.

✅ Initial Setup

• Installed Exchange 2019 CU15 on a brand-new Server 2025 machine.
• Completed prerequisites and configured IIS for the Exchange Server SE upgrade.
• Successfully upgraded to Exchange Server SE, verified core service roles and paths.

🔍 Diagnostic Tool: EMTshooter Enhancements

To improve traceability and modular diagnostics, I reworked the EMTshooter.ps1 script to include:

• 📄 Separate diagnostic logging to prevent transcript file conflicts.
• 🔁 Automated fallback from HTTP to HTTPS PowerShell session.
• 🔐 Credential prompt with optional internal SSL bypass.
• 📋 Inline error handling for WinRM, IIS, and Exchange components.

📋 Latest Diagnostic Results

The new script revealed valuable environment insights:

• ✅ WebAdministration module loaded successfully.
• ✅ WinRM connectivity confirmed via Test-WSMan.
• ✅ Exchange install path check passed.
• ✅ IIS bindings verified:
  • HTTP: *:80: and 127.0.0.1:80:
  • HTTPS: 127.0.0.1:443: and *:443:
• ✅ PowerShell Virtual Directory confirmed at:
  IIS://EXCHANGE/W3SVC/1/ROOT/PowerShell

⚠️ Remote PowerShell Connection Attempts

1️⃣ Attempted via HTTP:

• Failed with:The WinRM client cannot process the request. It cannot determine the content type of the HTTP response.

This suggests the endpoint exists but the configuration (likely SSL enforcement or misaligned headers) is blocking session creation.

2️⃣ Attempted via HTTPS with fallback:

• Prompted for credentials.
• Failed with:Basic authentication is currently disabled in the client configuration.

This indicates that the PowerShell client configuration (winrm set winrm/config/client/auth) does not allow Basic auth over HTTPS—even though the server may require it.

🔧 Next Steps

• Enable Basic Authentication on the client machine (if policy permits): winrm set winrm/config/client/auth '@{Basic="true"}'
• Evaluate whether the /PowerShell virtual directory requires SSL and whether it's configured for Windows or Basic authentication.
• Optionally rebuild the PowerShell vDir: Remove-PowerShellVirtualDirectory -Identity "PowerShell (Default Web Site)" New-PowerShellVirtualDirectory -Name "PowerShell" -WebSiteName "Default Web Site"

🎯 Conclusion The new script and diagnostics give deeper visibility into where remote session negotiation fails—allowing targeted fixes for authentication configuration and IIS endpoint behavior. Once these final issues are addressed, Exchange remote management via PowerShell should be fully operational.

If others in the community are running into similar connectivity symptoms post-upgrade to Exchange SE on Server 2025, I'd welcome your insights or refinements.