Azure SQL Private Endpoints: Why Your VPN Users Can't Connect (And What Actually Works)

We deployed an Azure VPN Gateway to give remote users secure access to Azure SQL databases through private endpoints. The setup looked textbook perfect: private endpoints approved and connected, VNet peering configured, routes in place, TCP connectivity verified. Everything worked except the one thing that mattered—users couldn’t authenticate. Here’s what we learned fighting Azure’s DNS architecture. The Setup That Should Have Worked Standard Azure private endpoint architecture for SQL Server: ...

December 12, 2025 · 7 min · Zac Lohrenz

Building Azure VPN with Terraform: Zero-Trust Authentication and GitOps

I needed VPN access to Azure resources across multiple subscriptions. The requirement was simple: secure access without managing additional credentials, no PSKs floating around, and everything infrastructure-as-code. Here’s how I built it. The Problem The Azure environment spans many subscriptions with overlapping IP ranges - a legacy of growth. We had: SQL Managed Instances requiring private connectivity Public SQL databases needing IP whitelisting Development teams needing ad-hoc access Zero appetite for managing VPN credentials separately from Azure AD Traditional VPN solutions would require: ...

November 21, 2025 · 7 min · Zac Lohrenz