10 days and 10 tips for Microsoft Tunnel Gateway: Day 1

Run the Readiness Tool

  • Always run mst-readiness.sh before installation
  • Validates OS, network, firewall, and system requirements
  • Saves you from troubleshooting issues that could’ve been caught upfront
  • Download from directly from Microsoft: https://aka.ms/microsofttunnelready

Key Parameters:

  • utils: System utilities, OS version, and required packages
    • No output = success. The script only prints errors when something fails. Don’t panic if you see nothing, that mean’s all checks passed
  • network: Connectivity to Intune endpoints, DNS resolution, and firewall rules
  • account: Account roles and licensing needed for installation

Run all checks: sudo ./mst-readiness.sh utils network account

⚠️ Heads up on the network check: In locked-down environments with restricted outbound connectivity, the script won’t show you which redirected host is actually blocked. If an endpoint redirects and the destination is blocked, you’ll just see a generic failure. That’s why I built my own diagnostic script to trace the full redirect chain – more on that next time. 🙂

Example: login.windows.net redirects to office.com – if office.com is blocked, the readiness script won’t tell you which one failed.

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