I can't attach files from my computer on a card. Drive or dropbox attachments are working just fine but when it comes to attaching a video or a sound from my computer the app does nothing. I tried on windows, macbook and also tried using different browsers, and finally tried on desktop app too instead of web, but none of them worked. But weirdly I can attach things like 9kb size, I'm not really sure if it is because of the format or the size of the file. And also the app on my phone works just fine, I don't have any problem uploading anything.
Look at this posts, maybe can help you
https://help.trello.com/article/769-adding-attachments-to-cards
https://help.dropbox.com/installs-integrations/third-party/trello
Cheers
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