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I've got a Kobo Glo HD and have the exact same problem - the "download all" option just plain doesn't work. Seems very clearly to be a software bug. Kobo support has been less than helpful. I got the device specifically for the Pocket integration so I've tried just about everything to fix it - removing the Pocket account and readding it, syncing with different options (only show articles that are downloaded on then off), hard reset - I haven't tried a factory reset and downgrade yet but I guess that's next.
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