I started a copy operation yesterday that Copy Handler estimated would take about 20 hours. The copy was to a network share in another location, over internet, so it was a bit slow. For some reason the copy operation had an error in the middle of the night and it sat there waiting for me to click "Retry", which I did in the morning, and the copy continued.
It would be great if you could add an Automatic Retry option and allow the interval/frequency of retries to be configured in minutes or seconds. My suggestion would be to have this feature enabled by default with an interval of 5 minutes.