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Expert knowledge for Azure VPN Gateway development including troubleshooting, best practices, decision making, architecture & design patterns, limits & quotas, security, configuration, integrations & coding patterns, and deployment.
Passed 8 of 14 test cases with the skill, and 11 of 14 without it.
1 fixed12 passed either way4 still failing5 broke
Tokens, turns and time describe resource use, not a dollar price.
This benchmark measured an earlier version of the skill.
A test case the skill fixed. Same model, same prompt, with and without the skill.
We are planning to upgrade our current gateway resource to a higher tier that supports Availability Zones to improve our high-availability posture. Give me a brief text summary explaining how to execute this tier change with the least amount of disruption, followed by a two-column markdown table comparing the expected impact for various transition paths.
| Checked | Without skill | With skill |
|---|---|---|
| Recommends deploying a new zone-redundant VPN Gateway AZ SKU | Missed | Passed |
| Addresses the migration of IPsec tunnels for the VPN Gateway transition | Missed | Passed |
| Does not recommend generic Application Gateway DNS swap methods | Missed | Passed |
The instructions your model reads when the skill loads.
This skill provides expert guidance for Azure VPN Gateway. Covers troubleshooting, best practices, decision making, architecture & design patterns, limits & quotas, security, configuration, integrations & coding patterns, and deployment. It combines local quick-reference content with remote documentation fetching capabilities.
IMPORTANT for Agent: Use the Category Index below to locate relevant sections. For categories with line ranges (e.g.,
L35-L120), useread_filewith the specified lines. For categories with file links (e.g.,[security.md](security.md)), useread_fileon the linked reference file
IMPORTANT for Agent: If
metadata.generated_atis more than 3 months old, suggest the user pull the latest version from the repository. Ifmcp_microsoftdocstools are not available, suggest the user install it: Installation Guide
This skill requires network access to fetch documentation content:
mcp_microsoftdocs:microsoft_docs_fetch with query string from=learn-agent-skill. Returns Markdown.fetch_webpage with query string from=learn-agent-skill&accept=text/markdown. Returns Markdown.| Category | Lines | Description |
|---|---|---|
| Troubleshooting | L37-L43 | Diagnosing and fixing Azure VPN Gateway issues: client prerequisites, packet captures, tunnel resets, connection health checks, and answers to common troubleshooting FAQs. |
| Best Practices | L44-L48 | Guidance on using network virtual appliances (NVAs) in Azure as VPN endpoints for remote access, including design, routing, security, and integration with Azure VPN Gateway. |
| Decision Making | L49-L58 | Guidance on choosing VPN Gateway SKUs and planning migrations: Linux VPN client, P2S protocols (SSTP to IKEv2/OpenVPN), client types, and Classic-to-Resource Manager gateways. |
| Architecture & Design Patterns | L59-L65 | Designing Azure VPN Gateway architectures: choosing topologies, active-active setups, cross-region peering, and high-availability connectivity patterns. |
| Limits & Quotas | L66-L70 | VPN Gateway client version history, SKU comparisons, and FAQs about gateway limits, scale, performance, and connection behavior |
| Security | L71-L88 | Securing Azure VPN Gateway: IPsec/IKE crypto, forced tunneling, P2S auth (Entra ID, RADIUS, MFA, Device SSO), access control, cert migration, roles/permissions, and security best practices. |
| Configuration | L89-L137 | Configuring Azure VPN Gateway and clients: P2S/S2S setup, auth (cert, Entra, RADIUS), routing/BGP, IPsec/NAT/traffic selectors, monitoring, and VNet/ExpressRoute connectivity. |
| Integrations & Coding Patterns | L138-L145 | Configuring Azure VPN with external systems: NPS/RADIUS user groups, S2S certificate tunnels, VPN over ExpressRoute, Cisco ASA setups, and BGP connections with AWS. |
| Deployment | L146-L155 | Deploying and upgrading Azure VPN Gateways (SKUs, zones, active/active), creating S2S VPNs via PowerShell/CLI, and distributing Azure VPN client profiles with Intune. |
| Topic | URL |
|---|---|
| Use packet capture on VPN Gateway for diagnostics | https://learn.microsoft.com/en-us/azure/vpn-gateway/packet-capture |
| Reset VPN Gateway or connection to restore IPsec tunnels | https://learn.microsoft.com/en-us/azure/vpn-gateway/reset-gateway |
| Verify Azure VPN Gateway connection health | https://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-verify-connection-resource-manager |
| Topic | URL |
|---|---|
| Use NVAs in Azure for remote access scenarios | https://learn.microsoft.com/en-us/azure/vpn-gateway/nva-work-remotely-support |
test cases passed, vs 11 / 14 without
More skills from the same source and nearby in the registry, with their headline benchmark lift.