TL;DR: We recently began seeing intermittent SSLHandshakeException errors when calling Microsoft login endpoints from our Java service. The root cause turned out to be missing root certificates in the Temurin Java images — even in recent versions. Microsoft had rotated their TLS chain, and the new root wasn’t bundled. We built a tool to dynamically extract the cert chain and patch the JVM truststore during our Docker build.

Over the past decade, I’ve spent most of my time in and around startups — from early-stage teams through IPOs in Silicon Valley to tech communities in New York. Along the way, I’ve picked up on a lot of the quirks, inside jokes, and shared language that tend to follow founders around. There’s something genuinely special about that environment — the energy, the optimism, the unwaivering desire to do something impactful and to change the world. I wanted to capture and preserve a bit of that spirit in a simple, tangible way.

I’ve recently taken an interest in vintage watches—specifically those from lesser-known brands. While many collectors focus on amassing collections of flagship models from the likes of Rolex, Omega, and JLC, the watches produced by smaller Swiss brands in the mid-20th century often offer extremely good value and the chance to own something truly unique.