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Same problem here ... I selected 3 comics to be downloaded to my Quest 2, then connected it via USB and ... nothing. The Supermedium Windows app still says "Connect your headset to transfer 3 files via USB". In the meantime I used Sidequest to load the Supermedium apk, ran the program, and could browse through all the comics on my PC, but the Supermedium desktop app is still telling me to connect the headset so it can transfer the files.

are you running the latest for both windows client and apk?