Number 2: Honey, We Shrunk the Operating System Windows CE 1.0 Devices (1996)
A journey of 1000 miles begins with a single step, but so does a descent into Hell. One such expedition began when Microsoft made its initial attempt to squeeze a Windows interface into a hand-held device. The NEC Mobile Pro 200 pictured above was one of nearly two dozen such devices--all of them "plagued with interoperability problems," notes Chris Tilley, author of "[[xref:http://www.hpcfactor.com/support/windowsce/|The History of Windows CE|The History of Windows CE]]."
Not only did the devices not support Microsoft's newly released Outlook, they didn't work with any non-Microsoft PIM or e-mail client. Win CE 1.0 handhelds were quickly rendered obsolete by [[xref:http://en.wikipedia.org/wiki/Windows_CE|Win CE 2.0 devices|Microsoft Windows CE]], which eventually begat Pocket PCs and Windows Mobile cell phones. More than 10 years later, Microsoft busily paving the road to mobile hell, and dragging millions of users along for the ride.