CLOUDY MUSINGS

You'd be surprised by the kinds of questions I get from customers these days. A lot of them start in places that feel familiar enough. Someone wants to understand Microsoft's decision to deprecate WSUS. Someone else is trying to figure out whether Azure Update Manager makes sense for their environment. Another customer is looking at Linux for the first time after spending most of their career in Windows-centric shops. On the surface, those sound like completely different conv

This topic comes up constantly. Sometimes it's at the start of a discovery conversation before we get into modernization, governance, platform engineering strategy, security, or cost optimization. Sometimes it's during a migration discussion where the existing documentation is incomplete or just plain wrong in the way only cloud infrastructure documentation can be. And sometimes it's simpler than any of that: someone just needs to know what's actually running in Azure across

As with previous blogs, working code and all relevant how-tos exist in this GitHub Repository! Clone, star, fork...whatever makes the most sense! You ever get halfway through a conversation about endpoint security or device posture and realize you're just kind of assuming everyone's on Windows 11 Enterprise? Not because you checked, not because anyone validated it recently, just because that's how it's always been said out loud. It feels settled, like something that got figur

One of the more interesting things about enterprise AI adoption is how quickly people become comfortable with these tools. We spent years teaching users to be skeptical of links, cautious with downloads, thoughtful about where sensitive data goes, and generally a little suspicious of shiny new software. Then AI assistants showed up, proved useful in about thirty seconds, and a lot of that caution went straight out the window. Suddenly people are pasting customer contracts in

I have watched some version of this play out enough times now that it almost feels like a rite of passage for organizations trying to mature their engineering operations. The symptoms are usually familiar. Incidents are happening too often, engineers are burned out, on-call has become something people dread, leadership wants fewer escalations, and somewhere in the middle of all that, someone says, “We need an SRE.” From there, a requisition gets approved, somebody smart gets

At some point you look across your repos and realize you've got some sort of split personality problem. Half your projects are on main, the other half are still on master, and every time you touch a pipeline, clone a repo, or write documentation, you have to stop and remember which one you're dealing with. You know it's not broken, it's just inconsistent enough to be a persistent low-grade annoyance. I recently went through this myself and thought about adding this to my blog