Agent skill

azure-application-gateway

Expert knowledge for Azure Application Gateway development including troubleshooting, best practices, decision making, limits & quotas, security, configuration, integrations & coding patterns, and deployment. Use when configuring listeners/routing, WAF/TLS, AGIC/AKS integration, autoscale/zone redundancy, or v1→v2 migration, and other Azure Application Gateway related development tasks. Not for Azure Front Door (use azure-front-door), Azure Load Balancer (use azure-load-balancer), Azure Traffic Manager (use azure-traffic-manager), Azure Firewall (use azure-firewall).

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2026-04-05

SKILL.md

Azure Application Gateway Skill

This skill provides expert guidance for Azure Application Gateway. Covers troubleshooting, best practices, decision making, 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

Category Lines Description
Troubleshooting L36-L41 Diagnosing and fixing Application Gateway runtime issues: backend health, 502s, certificates/Key Vault, listeners, session affinity, mTLS, redirects, AKS/ALB/containers, and HTTP response codes.
Best Practices L42-L46 Guidance on designing Application Gateway for very high traffic: sizing, autoscaling, performance tuning, capacity planning, and configuration patterns to handle large loads reliably.
Decision Making L47-L56 Guidance on choosing networking and pricing for Application Gateway, and planning migrations (AGIC to containers, v1 retirement, classic VMs to ARM)
Limits & Quotas L57-L63 Autoscaling and zone redundancy settings, gateway capacity and configuration limits, and guidance for migrating from Application Gateway v1 to v2.
Security L64-L105 TLS/SSL, certificates, mTLS, WAF, DDoS, HSTS, and secure access patterns for Application Gateway and App Gateway for Containers, including Key Vault, cert-manager, and protocol/cipher policies
Configuration L106-L170 Configuring and monitoring Azure Application Gateway and Application Gateway for Containers: listeners, routing, probes, health, headers/URL rewrite, session affinity, diagnostics, and AKS/AGIC integration.
Integrations & Coding Patterns L171-L178 Patterns for integrating App Gateway for Containers with monitoring, security, and scaling: Prometheus/Grafana, Istio, Sentinel/Defender, and autoscaling AKS pods via gateway metrics.
Deployment L179-L193 Guides for deploying and migrating Application Gateway (v1→v2, IPv6, mTLS), configuring autoscale, and setting up/upgrading AGIC with AKS using portal, ARM, PowerShell, and Helm.

Troubleshooting

Topic URL
Use ALB Controller backend health and metrics for troubleshooting https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/alb-controller-backend-health-metrics
Troubleshoot common issues in Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/troubleshooting-guide

Best Practices

Topic URL
Plan Application Gateway for high traffic volume scenarios https://learn.microsoft.com/en-us/azure/application-gateway/high-traffic-support

Decision Making

Topic URL
Choose container networking for Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/container-networking
Plan migration from AGIC to Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/migrate-from-agic-to-agc
Estimate and understand pricing for Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/understanding-pricing
Plan migration for Azure Application Gateway V1 retirement https://learn.microsoft.com/en-us/azure/application-gateway/retirement-faq
Understand billing and pricing for Azure Application Gateway SKUs https://learn.microsoft.com/en-us/azure/application-gateway/understanding-pricing
FAQ for migrating classic VMs to Azure Resource Manager https://learn.microsoft.com/en-us/previous-versions/azure/virtual-machines/migration/migration-classic-resource-manager-faq

Limits & Quotas

Topic URL
Configure autoscaling and zone redundancy for Application Gateway v2 https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-autoscaling-zone-redundant
Reference common limits and behaviors for Azure Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-faq
Plan migration from Application Gateway v1 to v2 https://learn.microsoft.com/en-us/azure/application-gateway/overview-v2

Security

Topic URL
Set listener-specific TLS/SSL policies on Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-configure-listener-specific-ssl-policy
Configure TLS protocol and cipher suite policy on Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-configure-ssl-policy-powershell
Configure end-to-end TLS on Application Gateway with PowerShell https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-end-to-end-ssl-powershell
Deploy a private Azure Application Gateway with restricted access https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-private-deployment
Secure Application Gateway session affinity cookie flags https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-secure-flag-session-affinity
Configure TLS policies and cipher suites for Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-ssl-policy-overview
Plan for TLS 1.0/1.1 retirement on Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-tls-version-retirement
Prepare certificates for backend authentication in Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/certificates-for-backend-authentication
Configure Key Vault-based TLS certificates via portal https://learn.microsoft.com/en-us/azure/application-gateway/configure-key-vault-portal
Integrate Key Vault certificates for TLS on Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/configure-keyvault-ps
Set up end-to-end TLS on Application Gateway via portal https://learn.microsoft.com/en-us/azure/application-gateway/end-to-end-ssl-portal
Enable FIPS 140-compliant mode on Application Gateway v2 https://learn.microsoft.com/en-us/azure/application-gateway/fips
Configure ECDSA and RSA TLS certificates on Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/ecdsa-rsa-certificates
Configure backend mTLS for Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-backend-mtls-gateway-api
Use cert-manager and Let’s Encrypt with Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-cert-manager-lets-encrypt-gateway-api
Integrate cert-manager and Let’s Encrypt with Application Gateway for Containers Ingress https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-cert-manager-lets-encrypt-ingress-api
Configure end-to-end TLS with Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-end-to-end-tls-gateway-api
Configure end-to-end TLS with Application Gateway for Containers Ingress https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-end-to-end-tls-ingress-api
Enable frontend mTLS on Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-frontend-mtls-gateway-api
Configure SSL offloading on Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-ssl-offloading-gateway-api
Configure SSL offloading using Ingress API for Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-ssl-offloading-ingress-api
Test and configure Web Application Firewall on Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-waf-gateway-api
Configure TLS policy for Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/tls-policy
Configure Web Application Firewall on Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/web-application-firewall
Add HSTS security header using Application Gateway rewrite https://learn.microsoft.com/en-us/azure/application-gateway/hsts-http-headers-portal
Use Let's Encrypt certificates with Application Gateway for AKS https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-letsencrypt-certificate-application-gateway
Configure JWT validation with Azure Application Gateway and Entra ID https://learn.microsoft.com/en-us/azure/application-gateway/json-web-token-overview
Use Azure Key Vault certificates for Application Gateway TLS termination https://learn.microsoft.com/en-us/azure/application-gateway/key-vault-certs
Export trusted client CA chains for Application Gateway client auth https://learn.microsoft.com/en-us/azure/application-gateway/mutual-authentication-certificate-management
Configure mutual TLS authentication on Azure Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/mutual-authentication-overview
Configure mutual TLS authentication on Application Gateway via portal https://learn.microsoft.com/en-us/azure/application-gateway/mutual-authentication-portal
Configure mutual TLS on Application Gateway with PowerShell https://learn.microsoft.com/en-us/azure/application-gateway/mutual-authentication-powershell
Renew TLS certificates for Azure Application Gateway listeners https://learn.microsoft.com/en-us/azure/application-gateway/renew-certificates
Generate self-signed certificates for Application Gateway v2 backends https://learn.microsoft.com/en-us/azure/application-gateway/self-signed-certificates
Manage listener TLS certificates in Azure Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/ssl-certificate-management
Protect Application Gateway with Azure DDoS Network Protection https://learn.microsoft.com/en-us/azure/application-gateway/tutorial-protect-application-gateway-ddos
Configure TLS termination on Application Gateway with CLI https://learn.microsoft.com/en-us/azure/application-gateway/tutorial-ssl-cli
Configure TLS termination on Application Gateway with PowerShell https://learn.microsoft.com/en-us/azure/application-gateway/tutorial-ssl-powershell

Configuration

Topic URL
Configure HTTP header rewrite in Application Gateway via PowerShell https://learn.microsoft.com/en-us/azure/application-gateway/add-http-header-rewrite-rule-powershell
Use backend health reports in Azure Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-backend-health
Configure custom probe in classic Application Gateway via PowerShell https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-create-probe-classic-ps
Create custom health probe in Application Gateway portal https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-create-probe-portal
Configure custom probe in Application Gateway via PowerShell https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-create-probe-ps
Configure and interpret Application Gateway diagnostic logs https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-diagnostics
Create and manage Application Gateway with ILB endpoint https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-ilb-arm
Use Azure Monitor metrics for Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-metrics
Health probe behavior and configuration in Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-probe-overview
Configure frontend IP addresses for Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/configuration-frontend-ip
Configure backend HTTP settings for Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/configuration-http-settings
Configure Azure Application Gateway infrastructure networking https://learn.microsoft.com/en-us/azure/application-gateway/configuration-infrastructure
Configure listeners and protocols on Azure Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/configuration-listeners
Configure core components of Azure Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/configuration-overview
Configure request routing rules in Azure Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/configuration-request-routing-rules
Configure Azure Monitor alerts for Application Gateway via templates https://learn.microsoft.com/en-us/azure/application-gateway/configure-alerts-with-templates
Configure private frontend IP for Application Gateway v1 https://learn.microsoft.com/en-us/azure/application-gateway/configure-application-gateway-with-private-frontend-ip
Configure Application Gateway with Azure App Service backend https://learn.microsoft.com/en-us/azure/application-gateway/configure-web-app
Create custom error pages in Azure Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/custom-error
Configure ALB Controller Helm chart for Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/alb-controller-helm-chart
Use Kubernetes API specification for Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/api-specification-kubernetes
Configure components of Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/application-gateway-for-containers-components
Use Azure Monitor metrics with Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/application-gateway-for-containers-metrics
Configure custom health probes for Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/custom-health-probe
Enable and use diagnostic logs for Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/diagnostics
Enable and configure gRPC support on Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/grpc
Configure HTTP header rewrite rules in Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-header-rewrite-gateway-api
Configure HTTP header rewrite using Ingress API for Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-header-rewrite-ingress-api
Configure multi-site hosting on Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-multiple-site-hosting-gateway-api
Configure multi-site hosting using Ingress API for Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-multiple-site-hosting-ingress-api
Set up path, header, and query string routing in Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-path-header-query-string-routing-gateway-api
Configure traffic splitting and weighted routing in Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-traffic-splitting-gateway-api
Configure URL redirect rules in Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-url-redirect-gateway-api
Configure URL redirects using Ingress API for Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-url-redirect-ingress-api
Configure URL rewrite rules in Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-url-rewrite-gateway-api
Configure URL rewrite using Ingress API for Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-url-rewrite-ingress-api
Configure WebSocket support in Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-websockets-gateway-api
Configure server-sent events with Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/server-sent-events
Configure ALB Service Mesh Helm chart for Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/service-mesh-helm-chart
Configure session affinity for Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/session-affinity
Use WebSocket protocol with Application Gateway for Containers https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/websockets
Configure readiness and liveness probes for AKS pods via Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-add-health-probes
Configure AGIC-specific Kubernetes ingress annotations https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-annotations
Configure cookie-based session affinity with Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-cookie-affinity
Expose AKS services over HTTP/HTTPS using Application Gateway ingress https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-expose-service-over-http-https
Expose WebSocket servers through Application Gateway with AGIC https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-expose-websocket-server
Enable multi-namespace support in Application Gateway Ingress Controller https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-multiple-namespace-support
Use private IPs for internal ingress routing with AGIC https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-private-ip
Monitor Azure Application Gateway with Azure Monitor https://learn.microsoft.com/en-us/azure/application-gateway/monitor-application-gateway
Reference for monitoring data from Azure Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/monitor-application-gateway-reference
Configure multi-site hosting on Azure Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/multiple-site-overview
Route traffic with parameter-based path selection in Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/parameter-based-path-selection-portal
Configure Private Link for Azure Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/private-link-configure
Configure request and response buffering in Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/proxy-buffers
Configure client IP preservation with Application Gateway Layer 4 proxy https://learn.microsoft.com/en-us/azure/application-gateway/proxy-protocol-header
Configure traffic redirection rules in Azure Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/redirect-overview
Configure HTTP header rewrite in Application Gateway portal https://learn.microsoft.com/en-us/azure/application-gateway/rewrite-http-headers-portal
Configure HTTP header and URL rewrite rules in Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/rewrite-http-headers-url
Configure URL and query string rewrite in Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/rewrite-url-portal
Create Application Gateway and configure header rewrite https://learn.microsoft.com/en-us/azure/application-gateway/tutorial-http-header-rewrite-powershell
Configure URL path-based routing in Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/url-route-overview

Integrations & Coding Patterns

Topic URL
Integrate App Gateway for Containers with Prometheus and Grafana https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/prometheus-grafana
Integrate Application Gateway for Containers with Istio service mesh https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/service-mesh-integration
Integrate Application Gateway for Containers logs with Microsoft Sentinel and Defender https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/siem-integration-with-sentinel
Autoscale AKS pods using Application Gateway metrics https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-autoscale-pods

Deployment

Topic URL
Configure externally managed scheduled autoscaling for Application Gateway v2 https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-externally-managed-scheduled-autoscaling
Deploy Application Gateway Basic (Preview) in portal https://learn.microsoft.com/en-us/azure/application-gateway/deploy-basic-portal
Disable and re-enable AGIC add-on on AKS clusters https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-disable-addon
Deploy AGIC using an existing Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-install-existing
Deploy AGIC with a new Application Gateway instance https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-install-new
Migrate AGIC from Helm deployment to AKS add-on https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-migration
Upgrade Application Gateway Ingress Controller using Helm https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-update-ingress-controller
ARM template for Application Gateway IPv6 frontend https://learn.microsoft.com/en-us/azure/application-gateway/ipv6-application-gateway-arm-template
Deploy Application Gateway IPv6 frontend with PowerShell https://learn.microsoft.com/en-us/azure/application-gateway/ipv6-application-gateway-powershell
Migrate Azure Application Gateway V1 to V2 with PowerShell https://learn.microsoft.com/en-us/azure/application-gateway/migrate-v1-v2
Deploy Application Gateway mTLS passthrough with ARM template https://learn.microsoft.com/en-us/azure/application-gateway/mutual-authentication-arm-template
Enable AGIC add-on for existing AKS and Application Gateway https://learn.microsoft.com/en-us/azure/application-gateway/tutorial-ingress-controller-add-on-existing

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