I think Microsoft's biggest mistake was trying to go to bat with the US carriers: trying to trade more control over things like software updates for terrible mistakes like timed exclusive releases with only one specific carrier. (Windows Phones were AT&T exclusive for bit; then there were various "flagship" phones alternating exclusivities between AT&T and Verizon depending on whom Microsoft needed to court better that phone hardware generation.)

Apple was able to do that because of a combo of first mover advantage and trend demand. Android didn't even bother, which lead to the obvious problems of the version diaspora of Android installs (who knew which phones on which carriers would get which updates and when), but playing ball with the weird control issues of carriers ultimately served Android pretty well in eventual market penetration, because the carriers were happiest to sell things they felt like they could control.