In case of an error you should clear the value if the fileupload component as this will prevent the update dialog. It should look and behave like you never selected a file after that.
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Thank you! Calling resetValue() on the file input component in the validator just before throwing ValidationException does the job!
I've added the filename to my validation error message so that the user can still see which file it was they tried to upload and I think that solves all my issues