I'm just reported what I am seeing and others have commented on here. Every time I plug any of my Touch, Glo, Aura H2O or Glo HD into a USB charger, I get the prompt. I know this hasn't always been the case. I'm pretty sure it changed with some firmware version, but it has been this way for at least a year.
If you are going to rely on plugged-into-charger to trigger an action, there will be people here whose devices will never see it. And of course there will be people here who never plug into a charger and always use the computer. Personally, I did that for at least the first two years of my Kobo ownership. I didn't have another device,that needed a charger, so there wasn't one plugged in where it was handy for me to use.
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