alt Hacker NewsAll tech enthusiasts at the time remember how amazing WinCE looked on the shelf. The thing that held it back was that it was just a cool technology, but wasn't an actual solution for any problem regular people had.
Regular people didn't need to carry around a pocket calendar or phone book. And most of the people who did -- carried paper ones that were easier to use didn't need charging.
Smartphones didn't get any traction until email started to take off, and Blackberry and Windows Mobile solved a problem by bringing email to handheld phones. And then they remained email devices for people who needed email on the go (business and tech-forward people)
Feature phones at the this time were catering to the two things people did want on the go: music and text messaging. Apple then started the smartphone consumer market by making a music-phone out of an iPod, and the rest is history.
Replies
The big issue with Wince was mobile IE was just an awful browser. I probably was not alone in wanting some 'webtop' gadget, but these weren't it. (In other words, iOS safari really was a killer app.)
The main problem was, that barely any useful apps existed. In the early 2000s internet connectivity was working well on those devices at some point (Wifi, via bluetooth phone, or integrated). But there was nothing to do with it, except syncing Outlook and some very limited mobile websites.
The only thing those Windows Mobile 2003 era devices were good for: Playing Age of Empires. There was a full featured port of Age of Empires I, and it was really awesome! It worked really well with the pen input.