Windows Mobile was a thing and sideloading was the standard method of installing applications. WinCE also had handwriting recognition built in to every device running locally on a 200MHz arm processor with 16 Meg of RAM. Programming was possible on WinCE 6 using .NET 2 or 3.5 as well as C++. It was very performant on a device with 64 Megs of RAM. I guess the problem was that versions after WinCE 7 binaries were not compatible with the previous versions as well as Microsoft working solely through OEM's for releases rather than direct to consumer like Apple or Google's partnerships. There were lots of also rans in the industry such as Palm OS Cobalt (6.0) not being used by anyone and the Amazon Fire.

Article from 2007 :

> Of course, the discussion included the upcoming Apple iPhone and Mr. Ballmer had a few funny things to say about the device.

>> It's sort of a funny question. Would I trade 96% of the market for 4% of the market? (Laughter.) I want to have products that appeal to everybody. Now we'll get a chance to go through this again in phones and music players. There's no chance that the iPhone is going to get any significant market share. No chance. It's a $500 subsidized item. They may make a lot of money. But if you actually take a look at the 1.3 billion phones that get sold, I'd prefer to have our software in 60% or 70% or 80% of them, than I would to have 2% or 3%, which is what Apple might get.

https://www.zdnet.com/article/steve-ballmerwindows-mobile-60...