Can you please do the following:
- (Re-)Start Cryptomator
- Unlock your vault and go into the parent folder of the item you want to delete
- Within Cryptomator’s settings enable debug logging
- Try to delete the item
- Disable debug logging
- Now send us the latest log file (found here). Redact any paths from the log that you don’t want us to see and feel free to send us a PN if you don’t want to post it publicly.