I agree, it was a calculated risk. Without getting into the deets I was confident it wouldn’t introduce any major issues. In fact NOT upgrading had resulted in

I agree, it was a calculated risk. Without getting into the deets I was confident it wouldn’t introduce any major issues. In fact NOT upgrading had resulted in problems that affected production a few weeks prior. Would I recommend a junior engineer yolo it? Of course not. But I’d also warn junior engineers to always keep a healthy skepticism when they are told “No, this cannot be done.” > There’s always a way to get housekeeping items approved… Yes, at a functional software shop, upgrades and maintenance are not considered stretch items. I did my best to make the case from a technical (bug fixes and features), business (vendor X won’t support us on this version), and customer (customer wouldn’t be happy if they knew we were running version X) standpoint. However, at a dysfunctional software shop, none of those factors matter (or they don’t matter as much).