There's no date/time section in the Settings, which is why I mentioned shell access. But it's a computer, there's a clock, and it matters
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A Kindlet failing to launch should never ever restart the device, so, you probably have much bigger issues on your hands, and mixing up "up to date" information with a ten year old mess means I have no idea in which state your device is.
Both KUAL and CR are fairly slow to startup, and the *first* launch will probably fail, especially if the device is busy. Second launch should be faster, though.
That's documented in the KUAL doc.