1---
2name: azure-application-gateway
3description: 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 listeners, WAF/TLS, AKS ingress/AGIC, autoscaling v2 gateways, or App Gateway for Containers, and other Azure Application Gateway related development tasks. Not for Azure Load Balancer (use azure-load-balancer), Azure Front Door (use azure-front-door), Azure Firewall (use azure-firewall), Azure Web Application Firewall (use azure-web-application-firewall).
4compatibility: Requires network access. Uses mcp_microsoftdocs:microsoft_docs_fetch or fetch_webpage to retrieve documentation.
5metadata:
6 generated_at: "2026-08-31"
7 generator: "docs2skills/1.0.0"
8---
9
10# Azure Application Gateway Skill
11
12This 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.
13
14## How to Use This Skill
15
16> **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
17
18> **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](https://github.com/MicrosoftDocs/mcp/blob/main/README.md)
19
20This skill requires **network access** to fetch documentation content:
21- **Preferred**: Use `mcp_microsoftdocs:microsoft_docs_fetch` with query string `from=learn-agent-skill`. Returns Markdown.
22- **Fallback**: Use `fetch_webpage` with query string `from=learn-agent-skill&accept=text/markdown`. Returns Markdown.
23
24## Category Index
25
26| Category | Lines | Description |
27|----------|-------|-------------|
28| Troubleshooting | L37-L42 | Diagnosing and fixing common Application Gateway for Containers issues using ALB Controller backend health, metrics, and troubleshooting guides for connectivity, routing, and configuration errors. |
29| Best Practices | L43-L48 | Tuning health probes, understanding probe behavior, and planning Application Gateway capacity, scaling, and configuration for high-traffic workloads. |
30| Decision Making | L49-L59 | Guidance on choosing networking and pricing for Application Gateway for Containers and planning/migrating between AGIC, v1/v2 gateways, and classic vs ARM VMs. |
31| Architecture & Design Patterns | L60-L64 | Guidance on choosing and designing load-balancing strategies and traffic distribution patterns when using Azure Application Gateway for Containers. |
32| Limits & Quotas | L65-L70 | Configuring autoscaling, zone redundancy, and multi-site hosting limits for Application Gateway v2, including capacity, scaling behavior, and site/hostname constraints. |
33| Security | L71-L111 | Configuring TLS/SSL, certificates, mTLS, Key Vault, cipher suites, FIPS, WAF, Private Link, and security headers for secure Azure Application Gateway and Containers deployments |
34| Configuration | L112-L174 | Configuring Application Gateway and Application Gateway for Containers: listeners, routing, probes, health, headers/URL rewrites, WebSockets, mTLS, Private Link, monitoring, alerts, and AKS/Ingress integration. |
35| Integrations & Coding Patterns | L175-L184 | Configuring header rewrites, integrating App Gateway (incl. containers) with Key Vault, Prometheus/Grafana, Istio, Sentinel/Defender, and using its metrics to autoscale AKS pods. |
36| Deployment | L185-L197 | Deploying and scaling Application Gateway and AGIC: portal/ARM/PowerShell setup, IPv6 frontends, AKS add-on enable/disable, migrations, and Helm-based upgrades. |
37
38### Troubleshooting
39| Topic | URL |
40|-------|-----|
41| 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 |
42| Troubleshoot common issues in Application Gateway for Containers | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/troubleshooting-guide |
43
44### Best Practices
45| Topic | URL |
46|-------|-----|
47| Health probe behavior and tuning for Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-probe-overview |
48| Plan Application Gateway for high traffic volume scenarios | https://learn.microsoft.com/en-us/azure/application-gateway/high-traffic-support |
49
50### Decision Making
51| Topic | URL |
52|-------|-----|
53| Choose container networking for Application Gateway for Containers | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/container-networking |
54| Decide and 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 |
55| Estimate and understand pricing for Application Gateway for Containers | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/understanding-pricing |
56| Migrate Azure Application Gateway from V1 to V2 | https://learn.microsoft.com/en-us/azure/application-gateway/migrate-v1-v2 |
57| FAQ for Azure Application Gateway V1 retirement and migration | https://learn.microsoft.com/en-us/azure/application-gateway/retirement-faq |
58| Plan migration from Application Gateway V1 to V2 | https://learn.microsoft.com/en-us/azure/application-gateway/v1-retirement |
59| Decide and plan migration from classic to Azure Resource Manager VMs | https://learn.microsoft.com/en-us/previous-versions/azure/virtual-machines/migration/migration-classic-resource-manager-faq |
60
61### Architecture & Design Patterns
62| Topic | URL |
63|-------|-----|
64| Choose load balancing strategies in Application Gateway for Containers | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/load-balancing-strategies |
65
66### Limits & Quotas
67| Topic | URL |
68|-------|-----|
69| Configure autoscaling and zone redundancy for Application Gateway v2 | https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-autoscaling-zone-redundant |
70| Configure multi-site hosting limits on Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/multiple-site-overview |
71
72### Security
73| Topic | URL |
74|-------|-----|
75| Configure listener-specific SSL policies in Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-configure-listener-specific-ssl-policy |
76| Configure TLS policy and cipher suites for Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-configure-ssl-policy-powershell |
77| Set up end-to-end TLS on Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-end-to-end-ssl-powershell |
78| Restrict access with private Azure Application Gateway deployment | https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-private-deployment |
79| Secure Application Gateway session affinity cookie flags | https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-secure-flag-session-affinity |
80| Configure TLS policies for Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-ssl-policy-overview |
81| 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 |
82| Prepare certificates for backend authentication in Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/certificates-for-backend-authentication |
83| Configure Key Vault TLS termination for Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/configure-key-vault-portal |
84| 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 |
85| Enable FIPS 140-compliant mode on Application Gateway v2 | https://learn.microsoft.com/en-us/azure/application-gateway/fips |
86| 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 |
87| 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 |
88| 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 |
89| 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 |
90| 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 |
91| 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 |
92| 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 |
93| 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 |
94| 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 |
95| 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 |
96| Configure TLS policy for Application Gateway for Containers | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/tls-policy |
97| Configure Web Application Firewall on Application Gateway for Containers | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/web-application-firewall |
98| Add HSTS security header using Application Gateway rewrite | https://learn.microsoft.com/en-us/azure/application-gateway/hsts-http-headers-portal |
99| 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 |
100| Configure JWT validation with Azure Application Gateway and Entra ID | https://learn.microsoft.com/en-us/azure/application-gateway/json-web-token-overview |
101| Use Azure Key Vault certificates for TLS termination on Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/key-vault-certs |
102| Export trusted client CA chains for Application Gateway client auth | https://learn.microsoft.com/en-us/azure/application-gateway/mutual-authentication-certificate-management |
103| Configure mutual TLS authentication on Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/mutual-authentication-overview |
104| Configure mutual TLS authentication on Application Gateway via portal | https://learn.microsoft.com/en-us/azure/application-gateway/mutual-authentication-portal |
105| Configure mutual TLS on Application Gateway with PowerShell | https://learn.microsoft.com/en-us/azure/application-gateway/mutual-authentication-powershell |
106| Secure workloads using Azure Application Gateway Private Link | https://learn.microsoft.com/en-us/azure/application-gateway/private-link |
107| Renew TLS certificates for Azure Application Gateway listeners | https://learn.microsoft.com/en-us/azure/application-gateway/renew-certificates |
108| Generate self-signed certificates for Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/self-signed-certificates |
109| Manage listener TLS certificates in Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/ssl-certificate-management |
110| Configure TLS termination on Application Gateway with CLI | https://learn.microsoft.com/en-us/azure/application-gateway/tutorial-ssl-cli |
111| Configure TLS termination on Application Gateway with PowerShell | https://learn.microsoft.com/en-us/azure/application-gateway/tutorial-ssl-powershell |
112
113### Configuration
114| Topic | URL |
115|-------|-----|
116| Use backend health reports in Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-backend-health |
117| Configure custom probe in classic Application Gateway via PowerShell | https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-create-probe-classic-ps |
118| Configure custom health probes for Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-create-probe-ps |
119| Configure and interpret Application Gateway diagnostic logs | https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-diagnostics |
120| Create and manage Application Gateway with ILB endpoint | https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-ilb-arm |
121| Use Azure Monitor metrics for Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-metrics |
122| Configure frontend IP addresses for Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/configuration-frontend-ip |
123| Configure backend HTTP settings for Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/configuration-http-settings |
124| Configure Azure Application Gateway network infrastructure | https://learn.microsoft.com/en-us/azure/application-gateway/configuration-infrastructure |
125| Configure listeners and protocols on Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/configuration-listeners |
126| Configure core components of Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/configuration-overview |
127| Configure request routing rules in Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/configuration-request-routing-rules |
128| Configure Azure Monitor alerts for Application Gateway via templates | https://learn.microsoft.com/en-us/azure/application-gateway/configure-alerts-with-templates |
129| Configure private frontend IP for Application Gateway v1 | https://learn.microsoft.com/en-us/azure/application-gateway/configure-application-gateway-with-private-frontend-ip |
130| Configure Application Gateway with Azure App Service backend | https://learn.microsoft.com/en-us/azure/application-gateway/configure-web-app |
131| Create custom error pages in Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/custom-error |
132| Configure ALB Controller using Helm chart parameters | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/alb-controller-helm-chart |
133| Configure Application Gateway for Containers via Kubernetes API | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/api-specification-kubernetes |
134| Configure core components of Application Gateway for Containers | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/application-gateway-for-containers-components |
135| 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 |
136| Configure custom health probes for Application Gateway for Containers | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/custom-health-probe |
137| Enable and use diagnostic logs for Application Gateway for Containers | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/diagnostics |
138| Enable and configure gRPC support on Application Gateway for Containers | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/grpc |
139| Configure CORS in Gateway API for Application Gateway for Containers | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-cors-gateway-api |
140| 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 |
141| 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 |
142| Configure Application Gateway for Containers inference gateway | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-inference-gateway |
143| 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 |
144| 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 |
145| 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 |
146| 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 |
147| 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 |
148| 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 |
149| 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 |
150| 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 |
151| Configure WebSocket support in Application Gateway for Containers | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/how-to-websockets-gateway-api |
152| Configure ALB Service Mesh extension via Helm chart | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/service-mesh-helm-chart |
153| Configure session affinity for Application Gateway for Containers | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/session-affinity |
154| Use WebSocket protocol with Application Gateway for Containers | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/websockets |
155| 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 |
156| Configure Azure Application Gateway Ingress Controller annotations | https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-annotations |
157| Configure cookie-based session affinity with Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-cookie-affinity |
158| 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 |
159| Expose WebSocket servers through Application Gateway with AGIC | https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-expose-websocket-server |
160| Enable multi-namespace support in Application Gateway Ingress Controller | https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-multiple-namespace-support |
161| Use private IPs for internal ingress routing with AGIC | https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-private-ip |
162| Monitor Azure Application Gateway with Azure Monitor | https://learn.microsoft.com/en-us/azure/application-gateway/monitor-application-gateway |
163| Use Azure Application Gateway monitoring metrics and logs | https://learn.microsoft.com/en-us/azure/application-gateway/monitor-application-gateway-reference |
164| Configure mTLS passthrough on Application Gateway via ARM | https://learn.microsoft.com/en-us/azure/application-gateway/mutual-authentication-arm-template |
165| Route traffic with parameter-based path selection in Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/parameter-based-path-selection-portal |
166| Configure Private Link for Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/private-link-configure |
167| Configure request and response buffering in Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/proxy-buffers |
168| Configure client IP preservation with Application Gateway Layer 4 proxy | https://learn.microsoft.com/en-us/azure/application-gateway/proxy-protocol-header |
169| Configure traffic redirection rules in Azure Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/redirect-overview |
170| Configure HTTP header rewrite in Application Gateway portal | https://learn.microsoft.com/en-us/azure/application-gateway/rewrite-http-headers-portal |
171| Configure HTTP header and URL rewrite on Application Gateway v2 | https://learn.microsoft.com/en-us/azure/application-gateway/rewrite-http-headers-url |
172| Configure URL and query string rewrite in Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/rewrite-url-portal |
173| Create Application Gateway and configure header rewrite | https://learn.microsoft.com/en-us/azure/application-gateway/tutorial-http-header-rewrite-powershell |
174| Configure URL path-based routing in Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/url-route-overview |
175
176### Integrations & Coding Patterns
177| Topic | URL |
178|-------|-----|
179| Configure HTTP header rewrite rules in Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/add-http-header-rewrite-rule-powershell |
180| Integrate Key Vault certificates with Application Gateway via PowerShell | https://learn.microsoft.com/en-us/azure/application-gateway/configure-keyvault-ps |
181| Integrate App Gateway for Containers with Prometheus and Grafana | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/prometheus-grafana |
182| Integrate Application Gateway for Containers with Istio | https://learn.microsoft.com/en-us/azure/application-gateway/for-containers/service-mesh-integration |
183| 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 |
184| Autoscale AKS pods using Application Gateway metrics | https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-autoscale-pods |
185
186### Deployment
187| Topic | URL |
188|-------|-----|
189| Configure externally managed scheduled autoscaling for Application Gateway v2 | https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-externally-managed-scheduled-autoscaling |
190| Deploy Azure Application Gateway Basic via portal | https://learn.microsoft.com/en-us/azure/application-gateway/deploy-basic-portal |
191| Disable and re-enable AGIC add-on on AKS clusters | https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-disable-addon |
192| Deploy AGIC using an existing Application Gateway | https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-install-existing |
193| Deploy AGIC with a new Application Gateway instance | https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-install-new |
194| Migrate AGIC from Helm deployment to AKS add-on | https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-migration |
195| Upgrade Application Gateway Ingress Controller using Helm | https://learn.microsoft.com/en-us/azure/application-gateway/ingress-controller-update-ingress-controller |
196| ARM template for Application Gateway IPv6 frontend | https://learn.microsoft.com/en-us/azure/application-gateway/ipv6-application-gateway-arm-template |
197| Deploy Application Gateway IPv6 frontend with PowerShell | https://learn.microsoft.com/en-us/azure/application-gateway/ipv6-application-gateway-powershell |
198| 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 |
gabrielmoreira