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Hi @Joe_Mako, thanks for calling this out! This should actually already be possible, but we replicated not being able to select multiple files at once to upload. It looks like you may have found a bug! We're waiting to hear back from our vendor and will keep you updated.
This idea was pushed back to New Idea due to a community updated completed in early April 2020 that updated the statuses on this board. This feature is actually currently available and as such this idea is being updated back to Implemented.
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