JSON Web Token (JWT) Validation in Azure Application Gateway: Secure Your APIs at the Gate
Hello Folks! In a Zero Trust world, identity becomes the control plane and tokens become the gatekeepers. Recently, in an E2E conversation with my colleague Vyshnavi Namani, we dug into a topic every ITPro supporting modern apps should understand: JSON Web Token (JWT) validation, specifically using Azure Application Gateway. In this post we’ll distill that conversation into a technical guide for infrastructure pros who want to secure APIs and backend workloads without rewriting applications. Why IT Pros Should Care About JWT Validation JSON Web Token (JWT) is an open standard token format (RFC 7519) used to represent claims or identity information between two parties. JWTs are issued by an identity provider (Microsoft Entra ID) and attached to API requests in an HTTP Authorization: Bearer <token> header. They are tamper-evident and include a digital signature, so they can be validated cryptographically. JWT validation in Azure Application Gateway means the gateway will check every incoming HTTPS request for a valid JWT before it forwards the traffic to your backend service. Think of it like a bouncer or security guard at the club entrance: if the client doesn’t present a valid “ID” (token), they don’t get in. This first-hop authentication happens at the gateway itself. No extra custom auth code is needed in your APIs. The gateway uses Microsoft Entra ID (Azure AD) as the authority to verify the token’s signature and claims (issuer/tenant, audience, expiry, etc.). By performing token checks at the edge, Application Gateway ensures that only authenticated requests reach your application. If the JWT is missing or invalid, the gateway could deny the request depending on your configuration (e.g. returns HTTP 401 Unauthorized) without disturbing your backend. If the JWT is valid, the gateway can even inject an identity header (x-msft-entra-identity) with the user’s tenant and object ID before passing the call along 9 . This offloads authentication from your app and provides a consistent security gate in front of all your APIs. Key benefits of JWT validation at the gateway: Stronger security at the edge: The gateway checks each token’s signature and key claims, blocking bad tokens before they reach your app. No backend work needed: Since the gateway handles JWT validation, your services don’t need token‑parsing code. Therefore, there is less maintenance and lower CPU use. Stateless and scalable: Every request brings its own token, so there’s no session management. Any gateway instance can validate tokens independently, and Azure handles key rotation for you. Simplified compliance: Centralized JWT policies make it easier to prove only authorized traffic gets through, without each app team building their own checks. Defense in depth: Combine JWT validation with WAF rules to block malicious payloads and unauthorized access. In short, JWT validation gives your Application Gateway the smarts to know who’s knocking at the door, and to only let the right people in. How JWT Validation Works At its core, JWT validation uses a trusted authority (for now it uses Microsoft Entra ID) to issue a token. That token is presented to the Application Gateway, which then validates: The token is legitimate The token was issued by the expected tenant The audience matches the resource you intend to protect If all checks pass, the gateway returns a 200 OK and the request continues to your backend. If anything fails, the gateway returns 403 Forbidden, and your backend never sees the call. You can check code and errors here: JSON Web Token (JWT) validation in Azure Application Gateway (Preview) Setting Up JWT Validation in Azure Application Gateway The steps to configure JWT validation in Azure Application Gateway are documented here: JSON Web Token (JWT) validation in Azure Application Gateway (Preview) Use Cases That Matter to IT Pros Zero Trust Multi-Tenant Workloads Geolocation-Based Access AI Workloads Next Steps Identify APIs or workloads exposed through your gateways. Audit whether they already enforce token validation. Test JWT validation in a dev environment. Integrate the policy into your Zero Trust architecture. Collaborate with your dev teams on standardizing audiences. Resources Azure Application Gateway JWT Validation https://learn.microsoft.com/azure/application-gateway/json-web-token-overview Microsoft Entra ID App Registrations https://learn.microsoft.com/azure/active-directory/develop/quickstart-register-app Azure Application Gateway Documentation https://learn.microsoft.com/azure/application-gateway/overview Azure Zero Trust Guidance https://learn.microsoft.com/security/zero-trust/zero-trust-overview Azure API Management and API Security Best Practices https://learn.microsoft.com/azure/api-management/api-management-key-concepts Microsoft Identity Platform (Tokens, JWT, OAuth2 https://learn.microsoft.com/azure/active-directory/develop/security-tokens Using Curl with JWT Validation Scenarios https://learn.microsoft.com/azure/active-directory/develop/v2-oauth2-client-creds-grant-flow#request-an-access-token Final Thoughts JWT validation in Azure Application Gateway is a powerful addition to your skills for securing cloud applications. It brings identity awareness right into your networking layer, which is a huge win for security and simplicity. If you manage infrastructure and worry about unauthorized access to your APIs, give it a try. It can drastically reduce the “attack surface” by catching invalid requests early. As always, I’d love to hear about your experiences. Have you implemented JWT validation on App Gateway, or do you plan to? Let me know how it goes! Feel free to drop a comment or question. Cheers! Pierre Roman
Unlocking Private IP for Azure Application Gateway: Security, Compliance, and Practical Deployment
If you’re responsible for securing, scaling, and optimizing cloud infrastructure, this update is for you. Based on my recent conversation with Vyshnavi Namani, Product Manager on the Azure Networking team, I’ll break down what private IP means for your environment, why it matters, and how to get started. Why Private IP for Application Gateway? Application Gateway has long been the go-to Layer 7 load balancer for web traffic in Azure. It manages, routes, and secures requests to your backend resources, offering SSL offloading and integrated Web Application Firewall (WAF) capabilities. But until now, public IPs were the norm, meaning exposure to the internet and the need for extra security layers. With Private IP, your Application Gateway can be deployed entirely within your virtual network (VNet), isolated from public internet access. This is a huge win for organizations with strict security, compliance, or policy requirements. Now, your traffic stays internal, protected by Azure’s security layers, and only accessible to authorized entities within your ecosystem. Key Benefits for ITPRO 🔒 No Public Exposure With a private-only Application Gateway, no public IP is assigned. The gateway is accessible only via internal networks, eliminating any direct exposure to the public internet. This removes a major attack vector by keeping traffic entirely within your trusted network boundaries. 📌 Granular Network Control Private IP mode grants full control over network policies. Strict NSG rules can be applied (no special exceptions needed for Azure management traffic) and custom route tables can be used (including a 0.0.0.0/0 route to force outbound traffic through on-premises or appliance-based security checkpoints). ☑️ Compliance Alignment Internal-only gateways help meet enterprise compliance and data governance requirements. Sensitive applications remain isolated within private networks, aiding data residency and preventing unintended data exfiltration. Organizations with “no internet exposure” policies can now include Application Gateway without exception. Architectural Considerations and Deployment Prerequisites To deploy Azure Application Gateway with Private IP, you should plan for the following: SKU & Feature Enablement: Use the v2 SKU (Standard_v2 or WAF_v2). The Private IP feature is GA but may require opt-in via the EnableApplicationGatewayNetworkIsolation flag in Azure Portal, CLI, or PowerShell. Dedicated Subnet: Deploy the gateway in a dedicated subnet (no other resources allowed). Recommended size: /24 for v2. This enables clean NSG and route table configurations. NSG Configuration: Inbound: Allow AzureLoadBalancer for health probes and internal client IPs on required ports. Outbound: Allow only necessary internal destinations; apply a DenyAll rule to block internet egress. User-Defined Routes (UDRs): Optional but recommended for forced tunneling. Set 0.0.0.0/0 to route traffic through an NVA, Azure Firewall, or ExpressRoute gateway. Client Connectivity: Ensure internal clients (VMs, App Services, on-prem users via VPN/ExpressRoute) can reach the gateway’s private IP. Use Private DNS or custom DNS zones for name resolution. Outbound Dependencies: For services like Key Vault or telemetry, use Private Link or NAT Gateway if internet access is required. Plan NSG and UDRs accordingly. Management Access: Admins must be on the VNet or connected network to test or manage the gateway. Azure handles control-plane traffic internally via a management NIC. Migration Notes: Existing gateways may require redeployment to switch to private-only mode. Feature registration must be active before provisioning. Practical Scenarios Here are several practical scenarios where deploying Azure Application Gateway with Private IP is especially beneficial: 🔐 Internal-Only Web Applications Organizations hosting intranet portals, HR systems, or internal dashboards can use Private IP to ensure these apps are only accessible from within the corporate network—via VPN, ExpressRoute, or peered VNets. 🏥 Regulated Industries (Healthcare, Finance, Government) Workloads that handle sensitive data (e.g., patient records, financial transactions) often require strict network isolation. Private IP ensures traffic never touches the public internet, supporting compliance with HIPAA, PCI-DSS, or government data residency mandates. 🧪 Dev/Test Environments Development teams can deploy isolated environments for testing without exposing them externally. This reduces risk and avoids accidental data leaks during early-stage development. 🌐 Hybrid Network Architectures In hybrid setups where on-prem systems interact with Azure-hosted services, Private IP gateways can route traffic securely through ExpressRoute or VPN, maintaining internal-only access and enabling centralized inspection via NVAs. 🛡️ Zero Trust Architectures Private IP supports zero trust principles by enforcing least-privilege access, denying internet egress, and requiring explicit NSG rules for all traffic—ideal for organizations implementing segmented, policy-driven networks. Resources https://docs.microsoft.com/azure/application-gateway/ https://learn.microsoft.com/azure/application-gateway/configuration-overview https://learn.microsoft.com/azure/virtual-network/network-security-groups-overview https://learn.microsoft.com/azure/virtual-network/virtual-network-peering-overview Next Steps Evaluate Your Workloads: Identify apps and services that require internal-only access. Plan Migration: Map out your VNets, subnets, and NSGs for a smooth transition. Enable Private IP Feature: Register and deploy in your Azure subscription. Test Security: Validate that only intended traffic flows through your gateway. Final Thoughts Private IP for Azure Application Gateway is an improvement for secure, compliant, and efficient cloud networking. If you’re an ITPRO managing infrastructure, now’s the time check out this feature and level up your Azure architecture. Have questions or want to share your experience? Drop a comment below. Cheers! Pierre
Deploy Dynamic Routing (BGP) between Azure VPN and Third-Party Firewall (Palo Alto)
Overview This blog explains how to deploy dynamic routing (BGP) between Azure VPN and a third-party firewall. You can refer to this topology and deployment guide in scenarios where you need VPN connectivity between an on-premises third-party VPN device and Azure VPN, or any cloud environment. What is BGP? Border Gateway Protocol (BGP) is a standardized exterior gateway protocol used to exchange routing information across the internet and between different autonomous systems (AS). It is the protocol that makes the internet work by enabling data routing between different networks. Here are some key points about BGP: Routing Between Autonomous Systems: BGP is used for routing between large networks that are under different administrative control, known as autonomous systems (AS). Each AS is assigned a unique number. Path Vector Protocol: BGP is a path vector protocol, meaning it maintains the path information that gets updated dynamically as routes are added or removed. This helps in making routing decisions based on path attributes. Scalability: BGP is designed to handle a large number of routes, making it highly scalable for use on the internet. Policy-Based Routing: BGP allows network administrators to set policies that can influence routing decisions. For example, administrators can prefer certain routes over others based on specific criteria such as path length or AS path. Peering: BGP peers are routers that establish a connection to exchange routing information. Peering can be either internal (within the same AS) or external (between different AS). Route Advertisement: BGP advertises routes along with various attributes such as AS path, next hop, and network prefix. This helps in making informed decisions on the best route to take. Convergence: BGP can take some time to converge, meaning to stabilize its routing tables after a network change. However, it is designed to be very stable once converged. Use in Azure: In Azure, BGP is used to facilitate dynamic routing in scenarios like connecting Azure VNets to on-premises networks via VPN gateways. This dynamic routing allows for more resilient and flexible network designs. Switching from static routing to BGP for your Azure VPN gateway will enable dynamic routing, allowing the Azure network and your on-premises network to exchange routing information automatically, leading to potentially better failover and redundancy. Why BGP? BGP is the standard routing protocol commonly used in the Internet to exchange routing and reachability information between two or more networks. When used in the context of Azure Virtual Networks, BGP enables the Azure VPN gateways and your on-premises VPN devices, called BGP peers or neighbors, to exchange "routes" that will inform both gateways on the availability and reachability for those prefixes to go through the gateways or routers involved. BGP can also enable transit routing among multiple networks by propagating routes a BGP gateway learns from one BGP peer to all other BGP peers. Diagram Pre-Requisite Firewall Network: Firewall with three interfaces (Public, Private, Management). Here, the LAB has configured with VM-series Palo Alto firewall. Azure VPN Network: Test VM, Gateway Subnet Test Network Connected to Firewall Network: Azure VM with UDR pointing to Firewall's Internal Interface. The test network should be peered with firewall network. Configuration Part 1: Configure Azure VPN with BGP enabled Create Virtual Network Gateway from marketplace Provide Name, Gateway type (VPN), VPN SKU, VNet (with dedicated Gateway Subnet), Public IP Enable BGP and provide AS number Create Note: Azure will auto provision a local BGP peer with an IP address from Gateway Subnet. After deployment the configuration will look similar to below. Make a note of Public IP and BGP Peer IP generated, we need this while configuring VPN at remote end. Create Local Network Gateway Local Network Gateway represents the firewall VPN network Configuration where you should provide remote configuration parameters. Provide Name, Remote peer Public IP In the Address space specify remote BGP peer IP (/32) (Router ID in case of Palo Alto). Please note that if you are configuring static route instead of dynamic you should advertise entire remote network ranges which you want to communicate through VPN. Here BGP making this process much simpler. In Advanced tab enable BGP and provide remote ASN Number and BGP peer IP create Create Connections with default crypto profile Once the VPN Gateway and Local Network Gateway has provisioned you can build connection which represents IPsec and IKE configurations. Go to VPN GW and under Settings, Add Connection Provide Name, VPN Gateway, Local Network Gateway, Pre-Shared Key Enable BGP If Required, Modify IPsec and IKE Crypto setting, else leave it as default Create Completed the Azure end configuration, now we can move to firewall side. Part 2: Configure Palo Alto Firewall VPN with BGP enabled Create IKE Gateway with default IKE Crypto profile Provide IKE Version, Local VPN Interface, Peer IP, Pre-shared key Create IPSec Tunnel with default IPsec Crypto profile Create Tunnel Interface Create IPsec Tunnel: Provide tunnel Interface, IPsec Crypto profile, IKE Gateway Since we are configuring route-based VPN, tunnel interface is very necessary to route traffic which needed to be encrypted. By this configuration your tunnel should be UP Now finish the remaining BGP Configurations Configure a Loopback interface to represent BGP virtual router, we have provided 10.0.17.5 IP for the interface, which is a free IP from public subnet. Configure virtual router Redistribution Profile Configure Redistribution Profile as below, this configuration ensures what kind of routers needed to be redistributed to BGP peer routers Enable BGP and configure local BGP and peer BGP parameters Provide Router ID, AS number Make sure to enable Install Route Option Configure EBGP Peer Group and Peer with Local BGP Peer IP, Remote (Azure)BGP Peer IP and Remote (Azure) BGP ASN Number. Also Specify Redistribution profile, make sure to enable Allow Redistribute Default Route, if you need to propagate default route to BGP peer router Create Static route for Azure BGP peer, 10.0.1.254/32 Commit changes Test Results Now we can test the connectivity, we have already configured necessary NAT and default route in Firewall. You can see the propagated route in both azure VPN gateway and Palo Alto firewall. FW NAT Name Src Zone Dst Zone Destination Interface Destination Address Service NAT Action nattovm1 any Untrust any untrust_inteface_pub_ip 3389 DNAT to VM1 IP nattovm2 any Untrust any untrust_interface_pub_ip 3000 DNAT to VM2 IP natto internet any Untrust ethernet1/1 default 0.0.0.0/0 SNAT to Eth1/1 Stattic Route configured: Azure VPN GW Connection Status and Propagated routes Azure Test VM1 (10.0.0.4) Effective routes Palo Alto BGP Summary Palo Alto BGP connection status Palo Alto BGP Received Route Palo Alto BGP Propagated Route Final Forwarding table Ping and trace result from Test VM1 to test VM2 Conclusion: BGP simplifies the route advertisement process. There are many more configuration options that we can try in BGP to achieve smooth functioning of routing. BGP also enables automatic redundancy and high availability. Hence, it is always recommended to configure BGP when it comes to production-grade complex networking.
