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azure-application-gateway

Expert knowledge for Azure Application Gateway development including troubleshooting, best practices, decision making, architecture & design patterns, limits & quotas, security, configuration, integrations & coding patterns, and deployment. Use when configuring App Gateway v2 listeners/routing, WAF/TLS with Key Vault, AKS/AGIC, Private Link, or Containers, 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 Virtual Network (use azure-virtual-network), Azure Web Application Firewall (use azure-web-application-firewall).

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MicrosoftDocs/Agent-Skills
Works withAzureKubernetes
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SKILL.md (original)

Review the instructions the agent will receive before you install.

Azure Application Gateway Skill

This skill provides expert guidance for Azure Application 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-L43Diagnosing backend health and metrics, interpreting health states, and troubleshooting configuration, connectivity, and runtime issues for Application Gateway and Application Gateway for Containers.
Best PracticesL44-L49Tuning health probes, understanding probe behavior, and planning Application Gateway capacity, scaling, and configuration for high-traffic workloads.
Decision MakingL50-L60Guidance on choosing networking and pricing for Application Gateway for Containers and planning/migrating from AGIC, App Gateway V1, and classic VMs to newer Azure offerings.
Architecture & Design PatternsL61-L65Guidance on choosing and designing load-balancing strategies and traffic distribution patterns when using Azure Application Gateway for Containers.
Limits & QuotasL66-L71Configuring autoscaling, zone redundancy, and multi-site hosting limits for Application Gateway v2, including capacity, scaling behavior, and site/hostname constraints.
SecurityL72-L112TLS/SSL and mTLS setup, cert prep/rotation, Key Vault integration, cipher/TLS policy config, WAF and security headers, private access, and FIPS/security hardening for Application Gateway and Containers
ConfigurationL113-L175Configuring Application Gateway and Application Gateway for Containers: listeners, routing, probes, health, headers/URL rewrites, WebSockets, HTTP/3, mTLS, Private Link, monitoring, and AKS/Ingress integration.
Integrations & Coding PatternsL176-L185Patterns and scripts for integrating App Gateway with AKS, Key Vault, Prometheus/Grafana, Sentinel/Defender, HTTP header rewrites, request mirroring, and autoscaling pods via gateway metrics
DeploymentL186-L198Deploying and scaling Application Gateway and AGIC: portal/ARM/PowerShell setup, IPv6 frontends, AKS add-on enable/disable, migrations, and Helm-based upgrades.

Troubleshooting

TopicURL
Diagnose backend health states in Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-backend-health
Use ALB Controller backend health and metrics for troubleshootinghttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/alb-controller-backend-health-metrics
Diagnose and fix Application Gateway for Containers issueshttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/troubleshooting-guide

Best Practices

TopicURL
Health probe behavior and tuning for Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-probe-overview
Plan Application Gateway for high traffic volume scenarioshttps://learn.microsoft.com/en-us/azure/application-gateway/high-traffic-support

Decision Making

TopicURL
Choose AKS networking for App Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/container-networking
Decide and plan migration from AGIC to Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/migrate-from-agic-to-agc
Estimate and understand pricing for Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/understanding-pricing
Migrate Azure Application Gateway from V1 to V2https://learn.microsoft.com/en-us/azure/application-gateway/migrate-v1-v2
FAQ for Azure Application Gateway V1 retirement and migrationhttps://learn.microsoft.com/en-us/azure/application-gateway/retirement-faq
Plan migration from Application Gateway V1 to V2https://learn.microsoft.com/en-us/azure/application-gateway/v1-retirement
Decide and plan migration from classic to Azure Resource Manager VMshttps://learn.microsoft.com/en-us/previous-versions/azure/virtual-machines/migration/migration-classic-resource-manager-faq

Architecture & Design Patterns

TopicURL
Choose load balancing strategies in Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/load-balancing-strategies

Limits & Quotas

TopicURL
Configure autoscaling and zone redundancy for Application Gateway v2https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-autoscaling-zone-redundant
Configure multi-site hosting limits on Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/multiple-site-overview

Security

TopicURL
Configure listener-specific SSL policies in Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-configure-listener-specific-ssl-policy
Configure TLS policy and cipher suites for Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-configure-ssl-policy-powershell
Set up end-to-end TLS on Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-end-to-end-ssl-powershell
Secure private-only access to Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-private-deployment
Secure Application Gateway session affinity cookie flagshttps://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-secure-flag-session-affinity
Configure TLS policies for Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-ssl-policy-overview
Plan for TLS 1.0/1.1 retirement on Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-tls-version-retirement
Prepare certificates for backend authentication in Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/certificates-for-backend-authentication
Configure Key Vault TLS termination for Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/configure-key-vault-portal
Set up end-to-end TLS on Application Gateway via portalhttps://learn.microsoft.com/en-us/azure/application-gateway/end-to-end-ssl-portal
Enable FIPS 140-compliant mode on Application Gateway v2https://learn.microsoft.com/en-us/azure/application-gateway/fips
Configure ECDSA and RSA TLS certificates on Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/ecdsa-rsa-certificates
Configure backend mTLS for Application Gateway for Containershttps://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 Containershttps://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 Ingresshttps://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 Containershttps://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 Ingresshttps://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 Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-frontend-mtls-gateway-api
Configure SSL offloading on Application Gateway for Containershttps://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 Containershttps://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 Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-waf-gateway-api
Configure Istio mTLS ingress with Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/service-mesh-integration
Configure Web Application Firewall on Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/web-application-firewall
Add HSTS security header using Application Gateway rewritehttps://learn.microsoft.com/en-us/azure/application-gateway/hsts-http-headers-portal
Use Let's Encrypt certificates with Application Gateway for AKShttps://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-letsencrypt-certificate-application-gateway
Configure JWT validation with Azure Application Gateway and Entra IDhttps://learn.microsoft.com/en-us/azure/application-gateway/json-web-token-overview
Configure Application Gateway TLS with Key Vault certificateshttps://learn.microsoft.com/en-us/azure/application-gateway/key-vault-certs
Export trusted client CA chains for Application Gateway client authhttps://learn.microsoft.com/en-us/azure/application-gateway/mutual-authentication-certificate-management
Configure mutual TLS authentication on Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/mutual-authentication-overview
Configure mutual TLS authentication on Application Gateway via portalhttps://learn.microsoft.com/en-us/azure/application-gateway/mutual-authentication-portal
Configure mutual TLS on Application Gateway with PowerShellhttps://learn.microsoft.com/en-us/azure/application-gateway/mutual-authentication-powershell
Secure Application Gateway access with Private Link endpointshttps://learn.microsoft.com/en-us/azure/application-gateway/private-link
Renew TLS certificates for Azure Application Gateway listenershttps://learn.microsoft.com/en-us/azure/application-gateway/renew-certificates
Generate self-signed certificates for Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/self-signed-certificates
Manage listener TLS certificates in Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/ssl-certificate-management
Configure TLS termination on Application Gateway with CLIhttps://learn.microsoft.com/en-us/azure/application-gateway/tutorial-ssl-cli
Configure TLS termination on Application Gateway with PowerShellhttps://learn.microsoft.com/en-us/azure/application-gateway/tutorial-ssl-powershell

Configuration

TopicURL
Configure custom probe in classic Application Gateway via PowerShellhttps://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-create-probe-classic-ps
Configure custom health probes for Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-create-probe-ps
Configure and interpret Application Gateway diagnostic logshttps://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-diagnostics
Create and manage Application Gateway with ILB endpointhttps://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-ilb-arm
Use Azure Monitor metrics for Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-metrics
Configure frontend IP addresses for Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/configuration-frontend-ip
Configure backend settings for Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/configuration-http-settings
Configure Azure Application Gateway network infrastructurehttps://learn.microsoft.com/en-us/azure/application-gateway/configuration-infrastructure
Configure Azure Application Gateway listeners and protocolshttps://learn.microsoft.com/en-us/azure/application-gateway/configuration-listeners
Configure core components of Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/configuration-overview
Configure request routing rules in Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/configuration-request-routing-rules
Configure Azure Monitor alerts for Application Gateway via templateshttps://learn.microsoft.com/en-us/azure/application-gateway/configure-alerts-with-templates
Configure private frontend IP for Application Gateway v1https://learn.microsoft.com/en-us/azure/application-gateway/configure-application-gateway-with-private-frontend-ip
Configure Application Gateway with Azure App Service backendhttps://learn.microsoft.com/en-us/azure/application-gateway/configure-web-app
Create custom error pages in Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/custom-error
Configure ALB Controller using Helm chart parametershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/alb-controller-helm-chart
Use Kubernetes API specification for Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/api-specification-kubernetes
Configure core components of Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/application-gateway-for-containers-components
Use Azure Monitor metrics with Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/application-gateway-for-containers-metrics
Configure custom health probes for Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/custom-health-probe
Enable and use diagnostic logs for Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/diagnostics
Enable and configure gRPC support on Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/grpc
Configure CORS in Gateway API for Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-cors-gateway-api
Configure HTTP header rewrite rules in Application Gateway for Containershttps://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 Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-header-rewrite-ingress-api
Configure Application Gateway for Containers inference gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-inference-gateway
Configure multi-site hosting on Application Gateway for Containershttps://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 Containershttps://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 Containershttps://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 Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-traffic-splitting-gateway-api
Configure URL redirect rules in Application Gateway for Containershttps://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 Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-url-redirect-ingress-api
Configure URL rewrite rules in Application Gateway for Containershttps://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 Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-url-rewrite-ingress-api
Configure WebSocket support in Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-websockets-gateway-api
Configure ALB Service Mesh extension via Helm charthttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/service-mesh-helm-chart
Configure session affinity for Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/session-affinity
Use WebSocket protocol with Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/websockets
Enable and configure HTTP/3 over QUIC in Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/http3-quic-support
Configure readiness and liveness probes for AKS pods via Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-add-health-probes
Configure Azure Application Gateway Ingress Controller annotationshttps://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-annotations
Configure cookie-based session affinity with Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-cookie-affinity
Expose AKS services over HTTP/HTTPS using Application Gateway ingresshttps://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-expose-service-over-http-https
Expose WebSocket servers through Application Gateway with AGIChttps://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-expose-websocket-server
Enable multi-namespace support in Application Gateway Ingress Controllerhttps://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-multiple-namespace-support
Use private IPs for internal ingress routing with AGIChttps://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-private-ip
Monitor Azure Application Gateway with Azure Monitorhttps://learn.microsoft.com/en-us/azure/application-gateway/monitor-application-gateway
Reference monitoring metrics and logs for Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/monitor-application-gateway-reference
Configure mTLS passthrough on Application Gateway via ARMhttps://learn.microsoft.com/en-us/azure/application-gateway/mutual-authentication-arm-template
Route traffic with parameter-based path selection in Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/parameter-based-path-selection-portal
Configure Private Link for Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/private-link-configure
Configure request and response buffering in Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/proxy-buffers
Configure client IP preservation with Application Gateway Layer 4 proxyhttps://learn.microsoft.com/en-us/azure/application-gateway/proxy-protocol-header
Configure traffic redirection rules in Azure Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/redirect-overview
Configure HTTP header rewrite in Application Gateway portalhttps://learn.microsoft.com/en-us/azure/application-gateway/rewrite-http-headers-portal
Configure HTTP header and URL rewrite on Application Gateway v2https://learn.microsoft.com/en-us/azure/application-gateway/rewrite-http-headers-url
Configure URL and query string rewrite in Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/rewrite-url-portal
Create Application Gateway and configure header rewritehttps://learn.microsoft.com/en-us/azure/application-gateway/tutorial-http-header-rewrite-powershell
Configure URL path-based routing in Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/url-route-overview

Integrations & Coding Patterns

TopicURL
Configure HTTP header rewrite rules in Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/add-http-header-rewrite-rule-powershell
Integrate Key Vault certificates with Application Gateway via PowerShellhttps://learn.microsoft.com/en-us/azure/application-gateway/configure-keyvault-ps
Configure request mirroring with Application Gateway for Containershttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-request-mirroring-gateway-api
Integrate App Gateway for Containers with Prometheus and Grafanahttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/prometheus-grafana
Integrate Application Gateway for Containers logs with Microsoft Sentinel and Defenderhttps://learn.microsoft.com/en-us/azure/application-gateway/for-containers/siem-integration-with-sentinel
Autoscale AKS pods using Application Gateway metricshttps://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-autoscale-pods

Deployment

TopicURL
Configure externally managed scheduled autoscaling for Application Gateway v2https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-externally-managed-scheduled-autoscaling
Deploy Azure Application Gateway Basic via portalhttps://learn.microsoft.com/en-us/azure/application-gateway/deploy-basic-portal
Disable and re-enable AGIC add-on on AKS clustershttps://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-disable-addon
Deploy AGIC using an existing Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-install-existing
Deploy AGIC with a new Application Gateway instancehttps://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-install-new
Migrate AGIC from Helm deployment to AKS add-onhttps://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-migration
Upgrade Application Gateway Ingress Controller using Helmhttps://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-update-ingress-controller
ARM template for Application Gateway IPv6 frontendhttps://learn.microsoft.com/en-us/azure/application-gateway/ipv6-application-gateway-arm-template
Deploy Application Gateway IPv6 frontend with PowerShellhttps://learn.microsoft.com/en-us/azure/application-gateway/ipv6-application-gateway-powershell
Enable AGIC add-on for existing AKS and Application Gatewayhttps://learn.microsoft.com/en-us/azure/application-gateway/tutorial-ingress-controller-add-on-existing

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