ReddRadar
Agent skill
azure-vpn-gateway
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. Use when configuring S2S/P2S tunnels, BGP routing, IPsec/IKE policies, Entra/RADIUS auth, or ExpressRoute VPNs, and other Azure VPN Gateway related development tasks. Not for Azure ExpressRoute (use azure-expressroute), Azure Virtual WAN (use azure-virtual-wan), Azure Virtual Network (use azure-virtual-network), Azure Virtual Network Manager (use azure-virtual-network-manager).
Install this agent skill to your Project
npx add-skill https://github.com/MicrosoftDocs/Agent-Skills/tree/main/skills/azure-vpn-gateway
Metadata
Additional technical details for this skill
- generator
- docs2skills/1.0.0
- generated at
- 2026-04-05
SKILL.md
Azure VPN Gateway Skill
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.
How to Use This Skill
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:
- Preferred: Use
mcp_microsoftdocs:microsoft_docs_fetchwith query stringfrom=learn-agent-skill. Returns Markdown. - Fallback: Use
fetch_webpagewith query stringfrom=learn-agent-skill&accept=text/markdown. Returns Markdown.
Category Index
| Category | Lines | Description |
|---|---|---|
| Troubleshooting | L37-L44 | Diagnosing and fixing Azure VPN Gateway issues: S2S/P2S connection failures, certificate/auth errors, macOS IKEv2, throughput, health checks, resets, and packet-capture/log-based debugging |
| Best Practices | L45-L49 | 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 | L50-L58 | Guidance on choosing VPN Gateway SKUs, understanding SKU mappings, migrating gateways and P2S protocols (SSTP→IKEv2/OpenVPN, Classic→ARM), and planning remote work with P2S VPN. |
| Architecture & Design Patterns | L59-L65 | Design patterns and guidance for choosing VPN Gateway topologies, configuring active-active gateways, and building highly available, resilient site-to-site connectivity. |
| Limits & Quotas | L66-L71 | VPN Gateway client version history, SKU comparisons, and FAQs about gateway limits, scale, performance, and connection behavior |
| Security | L72-L94 | Securing Azure VPN Gateway: IPsec/IKE policies, forced tunneling, cert/RADIUS auth, Entra ID & MFA for P2S, client config (Win/macOS/Linux), access control, roles, and crypto best practices. |
| Configuration | L95-L151 | Configuring Azure VPN Gateway and clients: P2S/S2S setup, auth (cert, Entra, RADIUS), BGP, IPsec/NAT, routing, monitoring, maintenance, and client configs for Windows, macOS, Linux, iOS. |
| Integrations & Coding Patterns | L152-L159 | Configuring Azure VPN Gateway with on-prem devices and services: NPS/RADIUS VSAs for P2S, S2S over ExpressRoute, Cisco ASA samples, and BGP VPN connectivity with AWS. |
| Deployment | L160-L173 | Deploying and migrating Azure VPN Gateways: create/upgrade gateways and SKUs, switch active/active modes, set up S2S VPNs, and manage client profiles and IP migrations via PowerShell/CLI. |
Troubleshooting
| Topic | URL |
|---|---|
| Run Azure VPN Client prerequisites check and fix issues | https://learn.microsoft.com/en-us/azure/vpn-gateway/azure-vpn-client-prerequisites-check |
| 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 |
Best Practices
| Topic | URL |
|---|---|
| Use NVAs in Azure for remote access scenarios | https://learn.microsoft.com/en-us/azure/vpn-gateway/nva-work-remotely-support |
Decision Making
| Topic | URL |
|---|---|
| Select appropriate Azure VPN Gateway SKU | https://learn.microsoft.com/en-us/azure/vpn-gateway/about-gateway-skus |
| Understand Azure VPN Gateway SKU consolidation mappings | https://learn.microsoft.com/en-us/azure/vpn-gateway/gateway-sku-consolidation |
| Migrate P2S connections from SSTP to IKEv2/OpenVPN | https://learn.microsoft.com/en-us/azure/vpn-gateway/ikev2-openvpn-from-sstp |
| Migrate VPN Gateways from Classic to Resource Manager | https://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-classic-resource-manager-migration |
| Plan remote work using P2S VPN Gateways | https://learn.microsoft.com/en-us/azure/vpn-gateway/work-remotely-support |
Architecture & Design Patterns
| Topic | URL |
|---|---|
| Design and configure active-active VPN Gateways | https://learn.microsoft.com/en-us/azure/vpn-gateway/about-active-active-gateways |
| Select Azure VPN Gateway topologies and designs | https://learn.microsoft.com/en-us/azure/vpn-gateway/design |
| Design highly available Azure VPN Gateway connectivity | https://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-highlyavailable |
Limits & Quotas
| Topic | URL |
|---|---|
| Compare Azure VPN Gateway legacy SKUs and limits | https://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-about-skus-legacy |
| Azure VPN Gateway FAQ with limits and behaviors | https://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-vpn-faq |
Security
Configuration
Integrations & Coding Patterns
| Topic | URL |
|---|---|
| Configure NPS RADIUS VSAs for P2S user groups | https://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-user-groups-radius |
| Configure S2S VPN over ExpressRoute private peering | https://learn.microsoft.com/en-us/azure/vpn-gateway/site-to-site-vpn-private-peering |
| Sample Cisco ASA configuration for Azure VPN Gateway | https://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-3rdparty-device-config-cisco-asa |
| Configure BGP VPN connection between Azure and AWS | https://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-howto-aws-bgp |
Deployment
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