AZ-500 Secure networking Practice Question
You need to securely connect an on-premises network to Azure over the internet with encrypted traffic. The connection must be site-to-site and use IPsec. Which Azure service should you use?
⚠ Common exam trap
Candidates often confuse Azure Virtual WAN as a direct replacement for VPN Gateway, but Virtual WAN still requires VPN Gateway instances for S2S IPsec termination and is an orchestration/management layer, not the underlying connectivity service.
Answer choices
Why each option matters
Answer the question above first, then reveal the full breakdown to understand why each option is right or wrong.
Correct answer & explanation
✓
Azure VPN Gateway
Azure VPN Gateway supports site-to-site (S2S) VPN connections over the internet using IPsec/IKE (IKEv1 or IKEv2) to encrypt traffic between an on-premises VPN device and Azure. This matches the requirement for an encrypted, internet-based site-to-site connection. ExpressRoute bypasses the internet entirely, Virtual WAN is a higher-level orchestration service that still relies on VPN Gateway for S2S IPsec, and Bastion is for RDP/SSH access to VMs without public IPs.
Answer analysis
Option-by-option breakdown
For each option: why learners choose it and why it is or isn't the right answer here.
- ✓
Azure VPN Gateway
Why this is correct
Azure VPN Gateway provides site-to-site connectivity over the public internet using IPsec/IKE encryption, terminating tunnels between on-premises VPN devices and the Azure virtual network gateway. This directly satisfies the encrypted, internet-based site-to-site IPsec requirement without dedicated private circuits.
- ✗
Azure ExpressRoute
Why it's wrong here
ExpressRoute provides a private, dedicated connection through a connectivity provider and does not traverse the public internet, so it cannot satisfy the requirement for encrypted traffic over the internet using IPsec. It is tempting because it delivers private, high-bandwidth, low-latency connectivity, and would be correct where traffic must bypass the internet entirely.
- ✗
Azure Virtual WAN
Why it's wrong here
Azure Virtual WAN is a networking service that aggregates branch, VPN and ExpressRoute connectivity through Microsoft's global transit network; it is not itself the IPsec site-to-site endpoint the scenario requires, which is a VPN gateway. It is tempting because Virtual WAN hubs can host site-to-site VPN, but that demands additional configuration beyond the stated requirement.
- ✗
Azure Bastion
Why it's wrong here
Azure Bastion provides RDP and SSH access to virtual machines through the Azure portal over TLS; it establishes no site-to-site IPsec tunnel between an on-premises network and Azure. It is tempting because it also delivers encrypted connectivity over the internet, but that connectivity terminates at individual VMs, not at network gateways.
Quick reference
VPN Protocol Comparison
| Protocol | Port | Encryption | Authentication | Use Case |
|---|---|---|---|---|
| IKEv2 / IPsec | UDP 500 / 4500 | AES-256 | Certificates / PSK | Site-to-site & remote access |
| SSL / TLS VPN | TCP 443 | TLS 1.3 | Certificates / MFA | Clientless remote access |
| L2TP / IPsec | UDP 1701 | AES (IPsec) | PSK / Certificates | Legacy remote access |
| WireGuard | UDP 51820 | ChaCha20 | Public keys | Modern high-performance VPN |
| PPTP | TCP 1723 | MPPE (weak) | MS-CHAPv2 | Legacy — avoid in production |
PPTP is considered insecure. IKEv2/IPsec and SSL VPN are the current recommended options.
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JA
Written by Johnson Ajibi, MSc IT Security
Senior Network & Security Engineer · founder of Courseiva
This AZ-500 practice question is part of Courseiva's free Microsoft certification practice question bank. Courseiva provides original exam-style practice questions with explanations, topic-based practice, mock exams, readiness tracking, and study analytics to help learners prepare for the AZ-500 exam.