Have you looked at the console log for any errors?
CristianoRiva
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I run into the same problem when transferring a file from WatchOS to iPhone.
How can I handle this kind of error?
The callback session(_ session: WCSession, didFinish fileTransfer: WCSessionFileTransfer, error: Error?) did not fire at all and the file transfer gets stuck.
Any news about this issue?
Unfortunately the suggested workaround does not work.