The feat Microsoft has to accomplish to do what they are doing is about 1000 harder than Tesla. Tesla has three known and very similar hardware configurations S, X, and E. They totally control the hardware. It has no third party software or drivers it has to be compatible with. It is so much easier its not even in the same league. And the distributions are so small something in the order of 300,000 vehicles.
Microsoft has to deal with an infinite number of possible hardware configurations they have no control over, a gigantic number of third party drivers. They have to maintain compatibility with all software ever released going back to the '90s or earlier. Different CPU architectures 32bit, 64bit with different instruction sets like ARM, AMD, Intel. 1.5 billion people run Windows. Imagine that distribution nightmare. Their insider program (customers who opt in to be beta testers) is probably larger than Tesla's entire distribution. Yet personally I feel, as the head IT guy of a small enterprise running a Microsoft shop, overall Windows has gotten less and less buggy over the years. I still maintain Tesla has a lot to learn from them.