I absolutely agree that it's very rare for a non-software engineering organisation to care one bit about its tech stack, at least outside of the IT departments.

I absolutely agree that it's very rare for a non-software engineering organisation to care one bit about its tech stack, at least outside of the IT departments. As long as things work reasonably well at a reasonable cost, the organisation will likely be happy about it. This is partly because IT (this includes software development) is seen as an expense center which provides a support function, akin to HR. Maybe some people will think this is silly, especially in companies where every employee spend all of their working time on some sort of digital device, but that's the reality that I have spent the past two decades working within, and I don't particularly mind it. I'm curious as to why you would disagree with what Adam Hess writes about handling updates though. To me he respectfully outlines that GitHub has engineering capabilities that allow them to update their Ruby on Rails weekly, and that it's a good idea to do so, if you can. I can follow you as far as how the application stack isn't the core business in the sort of organisations you and I seem to work for, and weekly updates likely shouldn't be your goal, but I do think that you should allocate the resources needed to keep things relatively up-to-date. I'll give you an example of how I don't follow my own advice. We have what has developed into an important asset management system that we build in-house, which due to a lack of updates being prioritized now cannot be build on the LTS version of it's core tech. This isn't a major problem today, because it's on an internal system on a virtual network which is heavily protected, but it's also gotten to the point where it will likely need one or two people to work full time for a week to a month to get it updated. Doing that might actually be cheaper than having kept it sort of up-to-date, maybe with quarterly or even yearly updates, but if we couldn't get those prioritized, how do you think we're going to get a week-month for updates prioritized? :p