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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. Use when configuring S2S/P2S VPNs, BGP routing, IPsec/IKE polici...

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SKILL.md

Full skill instructions

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), use read_file with the specified lines. For categories with file links (e.g., [security.md](security.md)), use read_file on the linked reference file

IMPORTANT for Agent: If metadata.generated_at is more than 3 months old, suggest the user pull the latest version from the repository. If mcp_microsoftdocs tools 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_fetch with query string from=learn-agent-skill. Returns Markdown.
  • Fallback: Use fetch_webpage with query string from=learn-agent-skill&accept=text/​markdown. Returns Markdown.

Category Index

CategoryLinesDescription
TroubleshootingL37-L44Diagnosing and fixing Azure VPN Gateway issues: client prerequisites, packet captures, tunnel resets, connection health checks, and answers to common troubleshooting FAQs.
Best PracticesL45-L49Guidance 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 MakingL50-L60Guidance on choosing VPN Gateway SKUs and public IPs, planning/​migrating gateways and clients (Linux, Classic, Basic), and shifting P2S protocols (SSTP→IKEv2/​OpenVPN) for remote access.
Architecture & Design PatternsL61-L67Design patterns and guidance for choosing VPN Gateway topologies, configuring active-active gateways, and building highly available, resilient site-to-site connectivity.
Limits & QuotasL68-L72VPN Gateway client version history, SKU comparisons, and FAQs about gateway limits, scale, performance, and connection behavior
SecurityL73-L94Configuring secure VPN connections: IPsec/​IKE policies, cert- and Entra-based auth, MFA/​RADIUS, access control, crypto requirements, and security best practices for Azure VPN Gateway.
ConfigurationL95-L155Configuring Azure VPN Gateway and clients: P2S/​S2S setup, auth (cert, Entra ID, RADIUS), routing/​BGP, IPsec/​NAT, monitoring, Always-On, and VNet/​ExpressRoute connectivity.
Integrations & Coding PatternsL156-L163Configuring 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.
DeploymentL164-L176Deploying 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

TopicURL
Run Azure VPN Client prerequisites check and fix issueshttps://learn.microsoft.com/en-us/azure/vpn-gateway/azure-vpn-client-prerequisites-check
Use packet capture on VPN Gateway for diagnosticshttps://learn.microsoft.com/en-us/azure/vpn-gateway/packet-capture
Reset VPN Gateway or connection to restore IPsec tunnelshttps://learn.microsoft.com/en-us/azure/vpn-gateway/reset-gateway
Verify Azure VPN Gateway connection healthhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-verify-connection-resource-manager

Best Practices

TopicURL
Use NVAs in Azure for remote access scenarioshttps://learn.microsoft.com/en-us/azure/vpn-gateway/nva-work-remotely-support

Decision Making

TopicURL
Select the right Azure VPN Gateway SKUhttps://learn.microsoft.com/en-us/azure/vpn-gateway/about-gateway-skus
Plan migration from Azure VPN Client for Linuxhttps://learn.microsoft.com/en-us/azure/vpn-gateway/azure-vpn-client-linux-retirement
Plan migration from Basic to Standard VPN public IPhttps://learn.microsoft.com/en-us/azure/vpn-gateway/basic-public-ip-migrate-about
Map and migrate Azure VPN Gateway SKUshttps://learn.microsoft.com/en-us/azure/vpn-gateway/gateway-sku-consolidation
Migrate P2S connections from SSTP to IKEv2/​OpenVPNhttps://learn.microsoft.com/en-us/azure/vpn-gateway/ikev2-openvpn-from-sstp
Migrate VPN Gateways from Classic to Resource Managerhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-classic-resource-manager-migration
Plan remote work using P2S VPN Gatewayshttps://learn.microsoft.com/en-us/azure/vpn-gateway/work-remotely-support

Architecture & Design Patterns

TopicURL
Design and configure active-active VPN Gatewayshttps://learn.microsoft.com/en-us/azure/vpn-gateway/about-active-active-gateways
Select Azure VPN Gateway topologies and designshttps://learn.microsoft.com/en-us/azure/vpn-gateway/design
Design highly available Azure VPN Gateway connectivityhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-highlyavailable

Limits & Quotas

TopicURL
Compare Azure VPN Gateway legacy SKUs and limitshttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-about-skus-legacy

Security

TopicURL
Implement forced tunneling for S2S VPN connectionshttps://learn.microsoft.com/en-us/azure/vpn-gateway/about-site-to-site-tunneling
Configure custom IPsec/​IKE policies in Azure portalhttps://learn.microsoft.com/en-us/azure/vpn-gateway/ipsec-ike-policy-howto
Enable multifactor authentication for P2S VPN usershttps://learn.microsoft.com/en-us/azure/vpn-gateway/openvpn-azure-ad-mfa
Configure P2S VPN with Entra ID and manual app registrationhttps://learn.microsoft.com/en-us/azure/vpn-gateway/openvpn-azure-ad-tenant
Manage Azure VPN Gateway root certificate rotationhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-about-gateway-certificate-migration
Migrate P2S Entra VPN from manual to Microsoft app IDhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-entra-gateway-update
Create or update custom Entra app ID for P2S VPNhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-entra-register-custom-app
Configure P2S access control by Entra users and groupshttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-entra-users-access
Configure macOS Azure VPN Client for Entra ID P2S authhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-entra-vpn-client-mac
Configure Device SSO with Azure VPN Client on Windowshttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-entra-vpn-client-windows-device-sso
Configure Azure VPN Gateway for P2S RADIUS authenticationhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-radius-gateway
Understand roles and permissions for VPN Gatewayhttps://learn.microsoft.com/en-us/azure/vpn-gateway/roles-permissions
Apply security best practices to Azure VPN Gatewayhttps://learn.microsoft.com/en-us/azure/vpn-gateway/secure-vpn-gateway
Use certificate authentication for S2S VPN connectionshttps://learn.microsoft.com/en-us/azure/vpn-gateway/site-to-site-certificate-authentication-gateway-about
Configure S2S certificate authentication using PowerShellhttps://learn.microsoft.com/en-us/azure/vpn-gateway/site-to-site-certificate-authentication-gateway-powershell
Meet cryptographic requirements for Azure VPN gatewayshttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-about-compliance-crypto
Configure custom IPsec/​IKE policies with PowerShellhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-ipsecikepolicy-rm-powershell
Integrate Azure P2S RADIUS with NPS for MFAhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-radius-mfa-nsp

Configuration

TopicURL
Generate P2S VPN client profiles for Entra authenticationhttps://learn.microsoft.com/en-us/azure/vpn-gateway/about-vpn-profile-download
Add or remove S2S connections on a VPN Gatewayhttps://learn.microsoft.com/en-us/azure/vpn-gateway/add-remove-site-to-site-connections
Configure optional Azure VPN Client settings for P2Shttps://learn.microsoft.com/en-us/azure/vpn-gateway/azure-vpn-client-optional-configurations
Configure BGP for VPN Gateway using Azure CLIhttps://learn.microsoft.com/en-us/azure/vpn-gateway/bgp-how-to-cli
Configure BGP for VPN Gateway using portalhttps://learn.microsoft.com/en-us/azure/vpn-gateway/bgp-howto
Create custom IPsec policies for P2S VPNhttps://learn.microsoft.com/en-us/azure/vpn-gateway/create-custom-policies-p2s-ps
Configure custom traffic selectors for VPN Gatewayhttps://learn.microsoft.com/en-us/azure/vpn-gateway/custom-traffic-selectors
Configure customer-controlled maintenance windows for VPN Gatewayhttps://learn.microsoft.com/en-us/azure/vpn-gateway/customer-controlled-gateway-maintenance
Configure monitoring for Azure VPN Gateway with Azure Monitorhttps://learn.microsoft.com/en-us/azure/vpn-gateway/monitor-vpn-gateway
Reference for Azure VPN Gateway monitoring datahttps://learn.microsoft.com/en-us/azure/vpn-gateway/monitor-vpn-gateway-reference
Configure NAT rules on Azure VPN Gatewayhttps://learn.microsoft.com/en-us/azure/vpn-gateway/nat-howto
View and disconnect Azure P2S VPN sessionshttps://learn.microsoft.com/en-us/azure/vpn-gateway/p2s-session-management
Configure Azure VPN Client for Linux with P2S certificateshttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-certificate-client-linux-azure-vpn-client
Configure P2S certificate authentication on VPN Gatewayhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-certificate-gateway
Generate P2S VPN certificates on Linux with OpenSSLhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-certificates-linux-openssl
Configure P2S VPN gateway with Entra ID clienthttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-entra-gateway
Configure Azure VPN Client on Linux with Entra IDhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-entra-vpn-client-linux
Configure Azure VPN Client with Entra ID on Windowshttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-entra-vpn-client-windows
Configure P2S VPN with RADIUS using PowerShellhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-how-to-radius-ps
Install P2S client certificates on Windows, macOS, Linuxhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-how-to-vpn-client-install-azure-cert
Configure P2S VPN user groups and IP poolshttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-user-groups-about
Update point-to-site VPN client profiles in Azurehttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-user-vpn-profile-update
Configure macOS native VPN client for P2S certificateshttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-vpn-client-cert-mac
Configure Linux strongSwan IKEv2 client for P2S certificateshttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-vpn-client-certificate-ike-linux
Configure iOS OpenVPN client for P2S certificate VPNhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-vpn-client-certificate-openvpn-ios
Configure Linux OpenVPN client for P2S certificate VPNhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-vpn-client-certificate-openvpn-linux
Configure macOS OpenVPN client for P2S certificate VPNhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-vpn-client-certificate-openvpn-mac
Configure Azure VPN Client on Windows for P2S certificateshttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-vpn-client-certificate-windows-azure-vpn-client
Configure Windows native client for P2S certificate VPNhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-vpn-client-certificate-windows-native
Configure OpenVPN 2.x Windows client for P2S certificateshttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-vpn-client-certificate-windows-openvpn-client
Configure OpenVPN 3.x Windows client for P2S certificateshttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-vpn-client-certificate-windows-openvpn-client-version-3
Configure VPN client for P2S RADIUS certificate authhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-vpn-client-configuration-radius-certificate
Configure VPN client for other P2S RADIUS methodshttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-vpn-client-configuration-radius-other
Configure VPN client for P2S RADIUS password authhttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-vpn-client-configuration-radius-password
Configure high-bandwidth S2S tunnels via ExpressRoutehttps://learn.microsoft.com/en-us/azure/vpn-gateway/site-to-site-high-bandwidth-tunnel
Configure forced tunneling for S2S VPN with Default Sitehttps://learn.microsoft.com/en-us/azure/vpn-gateway/site-to-site-tunneling
Overview of partner VPN device configurations for Azurehttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-3rdparty-device-config-overview
Understand Point-to-Site VPN routing behavior in Azurehttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-about-point-to-site-routing
Supported VPN devices and IPsec parameters for Azurehttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-about-vpn-devices
Azure VPN Gateway resource and connection settingshttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-about-vpn-gateway-settings
Configure BGP for VPN Gateway using PowerShellhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-bgp-resource-manager-ps
Generate P2S VPN certificates using Windows PowerShellhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-certificates-point-to-site
Generate P2S VPN certificates on Linux with strongSwanhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-certificates-point-to-site-linux
Generate P2S VPN certificates using MakeCerthttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-certificates-point-to-site-makecert
Connect classic VNets to ARM VNets via portalhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-connect-different-deployment-models-portal
Connect classic VNets to ARM VNets with PowerShellhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-connect-different-deployment-models-powershell
Connect route-based gateway to multiple policy-based deviceshttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-connect-multiple-policybased-rm-ps
Configure Windows Always-On VPN device tunnel to Azurehttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-howto-always-on-device-tunnel
Configure macOS Always-On VPN device tunnel to Azurehttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-howto-always-on-device-tunnel-macos
Configure Windows Always-On VPN user tunnel to Azurehttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-howto-always-on-user-tunnel
Configure P2S VPN with certificate auth using PowerShellhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-howto-point-to-site-rm-ps
Connect VNets with VNet-to-VNet using Azure CLIhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-howto-vnet-vnet-cli
Configure VNet-to-VNet VPN connection in portalhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-howto-vnet-vnet-resource-manager-portal
Advertise custom routes to P2S VPN clientshttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-p2s-advertise-custom-routes
Configure VPN gateway transit for VNet peeringhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-peering-gateway-transit
Connect VNets with VNet-to-VNet using PowerShellhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-vnet-vnet-rm-ps
Configure and troubleshoot Azure VPN Gateway connectionshttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-vpn-faq

Integrations & Coding Patterns

TopicURL
Configure NPS RADIUS VSAs for P2S user groupshttps://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-user-groups-radius
Configure S2S VPN over ExpressRoute private peeringhttps://learn.microsoft.com/en-us/azure/vpn-gateway/site-to-site-vpn-private-peering
Sample Cisco ASA configuration for Azure VPN Gatewayhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-3rdparty-device-config-cisco-asa
Configure BGP VPN connection between Azure and AWShttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-howto-aws-bgp

Deployment

TopicURL
Execute Basic-to-Standard public IP migration for VPN Gatewayhttps://learn.microsoft.com/en-us/azure/vpn-gateway/basic-public-ip-migrate-howto
Create a Basic SKU VPN Gateway via PowerShellhttps://learn.microsoft.com/en-us/azure/vpn-gateway/create-gateway-basic-sku-powershell
Deploy a VPN Gateway using PowerShellhttps://learn.microsoft.com/en-us/azure/vpn-gateway/create-gateway-powershell
Deploy a VPN Gateway using Azure CLIhttps://learn.microsoft.com/en-us/azure/vpn-gateway/create-routebased-vpn-gateway-cli
Deploy zone-redundant VPN and ExpressRoute gatewayshttps://learn.microsoft.com/en-us/azure/vpn-gateway/create-zone-redundant-vnet-gateway
Change Azure VPN Gateway between active and active-activehttps://learn.microsoft.com/en-us/azure/vpn-gateway/gateway-change-active-active
Upgrade Azure VPN Gateway SKU with minimal downtimehttps://learn.microsoft.com/en-us/azure/vpn-gateway/gateway-sku-upgrade
Create S2S VPN with shared key using PowerShellhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-create-site-to-site-rm-powershell
Create S2S VPN with shared key using Azure CLIhttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-howto-site-to-site-resource-manager-cli
Deploy Azure VPN client profiles using Intunehttps://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-profile-intune