I tried setting up a file field as a dependent based on the value of a taxonomy field. When you upload a file into the file field everything works as intended. The issue I have run into is when you want to switch the dependee value and remove the file in the file field. I can successfully remove the file from the file field but when I save the form the file is still there. When I remove the condition and am no longer applying a dependent dependee relationship I can successfully remove the file from the node. I tried playing with the settings within the conditional field but could not figure out if I was configuring it incorrectly or if this in an actual bug.

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I am having the same issue!
Any progress on this? Did you ever find out how to make it work?