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Ruputer/OnHand PC? Another smartwatch from late 90's/early 2000s. The specs were on part with the original Mac, 128KB RAM, with 102x64 pixel display and 2MB of flash, but VERY sluggish OS and poor battery life (but still better than modern smartwatches).

Maybe Palm and Psion devices count? I would exclude WinCE...

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Ah yes http://pconhand.com I drooled over it as a teen. But the price was to high for me.

i could never get used to the psion 5mx keyboard. it was just a little too small. the treo thumb-board wasn't ideal, but it worked well enough. FWIW, PalmOS was HEAVILY influenced by MacOS classic. I mean, at least they changed the variable names in the debug images.

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