If you’ve ever tried to glue together Azure’s certificate‑based point‑to‑site VPN on macOS, you know it’s a bit like performing a summoning ritual in an unknown language while balancing on a unicycle. My client’s team discovered this the hard way when they decided to secure their Azure Functions behind a Private Endpoint. What followed was a hilariously frustrating journey filled with bizarre errors, mismatched documentation, and the ultimate conclusion: sometimes you have to laugh (and maybe open your firewall instead). Join me as I recount this chaotic adventure into the depths of Azure VPN troubleshooting!