Thanks for the post.
the first thing is to install the ipac software and try see if the syetm can sysnc.
when properly configured there should be an ipac icon in my computer, open this folderand other sub folders will be visible,if you have an SD card media in this device it will be visibleas well. try copy the music of your choice from the system into the music folder or your sd card depending on your pref.
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The Microsoft Windows Mobile Device Center requires that the first sync be made via the USB sync cable. After the h4150 is plugged into the Vista machine, the WMDC opens and prompts you through setting up a partnership. Then you can set the h4150 to sync via Bluetooth.
ActiveSync works fine with Vista. Ignore that other guys post.
connect the usb cable to the pocket pc. then, with pc on, plug the opposite end to the pc usb port. then, open My Computer" icon on desktop and then find the drive letter associated with the pocket pc. for example, if your pc has only one hard drive and one cd-rom drive, then your pocket pc letter will be e:. double-click e drive and verify your pocket pc. then mouse-drag any files from outlook folder into the e: drive. they will be copied, by default. the originals will still be on the pc.
It might be a hardware problem - if you get it both with the cradle and a sync cable, then it might be the connector at bottom of Ipaq. But I don't know for sure. If it's intermittent like this then it doesn't seem like a software problem.