Azure VPN Gateway

VPN Gateway Pre-Deployment Checklist

Azure VPN Gateway P2S — Entra ID authenticated, all prerequisites and configuration decisions

Azure Networking

A comprehensive pre-deployment checklist for Azure VPN Gateway Point-to-Site (P2S) deployment using Entra ID authentication.

This list covers networking prerequisites, identity & access, Entra ID authentication, gateway configuration, P2S client setup, monitoring & diagnostics, and IaC deployment patterns.

Work through each section to prepare for your resource deployment.

GitHub View IaC on GitHub → Resource templates, deployment scripts, and other helpful information.
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▶ ARM Items marked ARM map to required properties in the ARM resource declaration — the portal will not submit and the ARM/Bicep template will fail validation without them.

Compliance alignment

This checklist is reviewed and maintained against three Microsoft architectural frameworks. Items within each section are tagged required, recommended, or optional based on framework guidance — with Zero Trust items typically driving the required bar, and Well-Architected pillar guidance informing the recommended set.

CAF
Cloud Adoption Framework
Governance & operations

Naming and tagging are applied consistently at deployment time: all resources follow the CAF pattern {type}-{workload}-{env}-{locationAbbr}-{namingIndex}, with Workload, Environment, and createdBy tags applied automatically. The deployment is designed for hub VNet integration and supports CAF landing zone architectures. Governance items address resource locks, Azure Policy compliance, and the additional CAF-recommended tags — CostCenter, DataClassification, BusinessUnit, and ServiceClass — that must be supplied via the -Tags parameter before deployment.

WAF
Well-Architected Framework
All five pillars

Reliability: zone-redundant AZ SKU selection, active-active mode evaluation, and Standard Static Public IP for predictable addressing. Security: Entra ID as the sole authentication mechanism, group-based access control, and Conditional Access policy as the critical post-deployment security item. Performance Efficiency: SKU selection based on concurrent connection count (250–1000) and Generation2 hardware for maximum throughput. Cost Optimization: SKU cost guidance (~$140–$530/month range) and budget alerting. Operational Excellence: full IaC with idempotent deployment, what-if validation, and timestamped deployment names.

ZT
Zero Trust
Verify, least privilege, assume breach

Verify explicitly: all P2S connections require Entra ID authentication — no certificates or shared keys distributed to clients. Group-based access with Assignment required enforced denies unenrolled users at the app layer. A Conditional Access policy requiring MFA and device compliance is the single most critical gap to address before production go-live. Least privilege: VPN access is scoped to a named security group, no standing credentials distributed, and PIM/JIT for operational teams. Assume breach: NSGs on workload subnets prevent lateral movement from connected VPN clients, and diagnostic logging to Log Analytics is required for connection auditing.