Hi Matt Van Der Male! That certainly is a concerning issue. I see that you have already submitted a case in your support group which is awesome. In the mean time, let's see if anyone else in the community has experienced this issue and may have a workaround.
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Is it possible that those spaces don't allow the Files type of content? You can see this by going directly to the spaces and seeing which kinds of content are marked as active for the place. I've run into this a couple of times where when the space was created, we didn't think we'd need a certain type of content. And then promptly forgot about that.
Best of luck!