For each job in the queue, yes. One destination per job.
I did some surface level troubleshooting this morning. Did a number of test transfers, a set of 8 directories containing 8x1GB files to the array.
Tried; Copy all to one directory, Copy all to different sub directories, Half and Half, using the tree to select destination, typing in destination.....
Maybe 80% of the transfers worked as expected, still a few which skipped items in the queue.
I'll try and sit down and do this a bit more methodically, hopefully the data can help track this down.