Because their strategy for getting their applications in front of everyone has always been to get Windows in front of everyone, and that meant having to support third party applications that they chose not to try to incorporate into their own apps, but which got enough usage that not supporting them would mean losing those Windows desktops, and thus losing those users of the MS applications that were on every Windows desktop.

It's quite possible that this attributes too much intentional strategy to MS, and also treats them as a single entity with a single strategy more than they deserve. The MS internal teams that were bending over backwards to maintain backwards compatibility were not the same as the teams that were churning out new APIs, building Azure, etc., and quite likely had very different incentives.

Ironically, Office was the original poster child for Microsoft reinventing it's own widget toolkits, even back when Microsoft had a coherent visual design and developer story.

I agree with most of that. To be charitable to Nadella, at the time he first came into the role, Microsoft needed someone yelling "Cloud! Cloud! Cloud!" because the company was certainly behind folks like AWS. But for a long time he basically stopped there. Office migrated to the cloud and they pushed out Azure. Then he went on the AI rant and they decided that putting AI into everything, whether customers wanted it or not, was "the next thing." But now we're learning that Azure is a steaming pile of crap with customers leaving, and this article about GUI strategy shows they don't have an application development strategy. Everybody is fed up with Windows. Everybody is fed up with all the numerous "CoPilots." You actually have regular people investigating moving off Windows to Linux desktops. The one thing that Microsoft did exceptionally well through the 1990s and early 2000s was keep enterprises and app developers moving in the same direction. They bent over backwards to keep old Windows 3.1 applications running even on Win32 systems. That all ensured that nobody questioned whether they would work with Microsoft. They were the default and they commanded huge market power because of it. But that's all changed, and they have nothing to replace it. With everybody starting to ask questions that Nadella doesn't have answers for, it's going in a bad direction. Nadella needs to call his EVPs to account and force them to make some hard decisions about what lives or dies and then pressure test the resulting strategy with his customers, both old customers and potential customers. Surely, cloud and AI are a part of that future strategy, but he needs to figure out the rest of it.

In theory, the market should be pricing in based on future potential. As it has become increasingly clear this past decade, the market is not rational.

In a bubble, everyone looks like they’re doing well. Don’t confuse that with an actual strategy.

Sure, but how much of that had to do with the design and implementation of Windows? You know, the OS that runs half of the modern economy. Microsoft is just milking it without a coherent vision.

Maybe financially MS is successful but at the cost of flagship product becoming adware and people fleeing slowly away

Cloud was taking off at the same time. Anybody in his spot would have been successful.

Stock price going up is not the success criterion for a business. Making money is. And Microsoft's decisions are undermining their ability to make money in the future, which makes them bad decisions even if the stock price has gone up or if they make more money in the short term.

If your only metric is stock price, yes. That’s the value proposition of enshittification.