I am trying to find any supporting information on the OS, I am assuming it is Windows CE 3.0, but can't even see where to find the version. Some questions, can you set themes for the today screen (according to Microsoft you can on CE, but I can't figure it out) and can it be automatically updated like other Windows OS?
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Re: Jornada 525 OS
To list your CE version, you can go to the Today screen and select the Start button to pull down the menu.
Select Settings (not HP settings). From the Settings screen, select the System tab at the bottom. At the top of this page, select About. This will list your CE version.
Mine is Version 3.0.9348 (Build 9616). It also will list the Processor (SH3) and Memory (15.87 MB).
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I use an Omnibook 500 with a Jornada 545 as you describe without problems. The most likely cause is the difference in processors. The first version of Pocket PC was supported on three different CPU architectures. The Jornada 545 uses an SH3 processor. Applications designed for the 565 will not run on the 545. You will need to find applications designed for the SH3 processor.
Only a hint. Did you check the small print via the downloads for Pocket PC on the Microsoft web pages? If you download from the regular OS pages they don't mention that certain Pocket PC generations are not supported.
I noticed this but only on Media Player downloads fom the pocket PC pages but it takes time to find this more detailed info.