Microsoft probably has a problem with tech debt, yes. That is however not the problem. Instead, the product strategy is. And it was bad even before LLMs.

Windows is under 10% of their revenue these days. It’s simply not important to leadership. Just like Xbox - just let it slowly die as you squeeze any last remaining cents out

Windows is a small part of their revenue on purpose, because the OS monopoly enables them to sell and push a lot of their other revenue streams. Windows has always been easy to pirate for the same reason.

But make no mistake, it is very important for Microsoft and leadership, or they wouldn't keep updating it so much and talking about it so much on their keynotes and marketing.

Nah, they have a good strategy. In fact, they have all the strategies.

This is true. The constantly changing strategy is what left the wave of debt behind it.