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Just checking that all gotchas have been checked off.
If you have a cover on your Kobo, it must be open and ON
Very shortly after connecting the cable, your Kobo should present you with a Connect? screen (I mention this, because this was very intermittent on my new Aura2. So bad I binned 2 cables I thought were bad. It now appears the connector was contaminated and need many uses before settling in.)
Your OS must see the device first, then Calibre can see it. IIRC some OS can only have 1 MTP device connected at a time. Some devices give you the option on what MODE to connect (simple USB, PTP or MTP), that may help if you need 2 devices connected at the same time
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