Now, I get why you made the quip, but I for one keep both of those out of the business I run for this exact reason: I do not trust MICROS~1 in the medium to long term.

I also present the CEO and board with other arguments, like moral ones about involvement in atrocities and tyranny, legal ones regarding things like data protection, market related ones such as the likelihood of a future showdown between the EU and US.

But the risk that MICROS~1 fucks us over directly is even easier for them to understand, because they have been using Windows and Office for decades and are quite queasy about 10 going EOL and what the next set of annoyances in document management will be that they'll have to suffer under. It's something they have immediate experience of and didn't like.

A year from now it's probable we'll only have a couple of Windows machines left, because some of our customers use software that doesn't run under Wine and tries to block execution under both debuggers and container environments.

I don't like to be seen as defending Microsoft, they definitely have their share of faults, but as far as business goes, I think Microsoft is the least likely company to screw you over as a (business) customer. Microsoft has kept old software working pretty much unchanged for the last 20 years. I know, I still have software built on early Windows 95/NT4 that works fine on Windows 11...and with some registry tweaks Windows 11 will run on a computer from 2005 without too many issues (sure, 3rd party security software and js-heavy web pages will be slow but that is not directly MS fault). Windows 10 EOL in 2025 is only for consumer level stuff, you can get Windows 10 support for enterprise for another 2 years at least and some versions even up to 2029, so again, if you are a business, you are taken care of (if you are "cheaping" you way with Windows Home and Pro in business then you kind of get what you pay for, I am sure you as a business don't give away free products/services for years on end). And you can keep using your Windows 10 after EOL, not like they lock you out, they just don't support you...just like you don't repair stuff for free after warranty end. Compare that to any other tech company that churns through HW and SW much faster and much more severely where old HW and SW no longer works or cannot connect to the internet or use the latest browser so you cannot connect to the latest HTTPS servers. Even open source software breaks compatibilty with older versions much more oftern than Microsoft, but since that is "free" people just shrug it off.