Ok well, this is the most efficient way that I know of to manually move files. If there is another method to move files that will not cause this problem, please let me know. Using network shares is not a good option as it takes significantly longer to transfer files this way.
Winscp has a GUI so all i do is right click, hit "move to" and put in the destination path. Here is what the winscp log shows after moving a simple text document (test2.txt) from the Downloads share to the Backup share.
2017-08-28 17:11:50.158 Moving file "test2.txt" to "/mnt/user/Backup/test2.txt".
> 2017-08-28 17:11:50.159 Type: SSH_FXP_RENAME, Size: 68, Number: 5394
> 2017-08-28 17:11:50.159 12,00,00,15,12,00,00,00,1D,2F,6D,6E,74,2F,75,73,65,72,2F,44,6F,77,6E,6C,6F,
> 2017-08-28 17:11:50.159 61,64,73,2F,74,65,73,74,32,2E,74,78,74,00,00,00,1A,2F,6D,6E,74,2F,75,73,65,
> 2017-08-28 17:11:50.159 72,2F,42,61,63,6B,75,70,2F,74,65,73,74,32,2E,74,78,74,
. 2017-08-28 17:11:50.159 Sent 72 bytes
. 2017-08-28 17:11:50.159 There are 0 bytes remaining in the send buffer
. 2017-08-28 17:11:50.159 Looking for network events
. 2017-08-28 17:11:50.159 Timeout waiting for network events
. 2017-08-28 17:11:50.159 Waiting for another 4 bytes
. 2017-08-28 17:11:50.159 Looking for incoming data
. 2017-08-28 17:11:50.159 Looking for network events
. 2017-08-28 17:11:50.160 Detected network event
. 2017-08-28 17:11:50.160 Enumerating network events for socket 2616
. 2017-08-28 17:11:50.160 Enumerated 1 network events making 1 cumulative events for socket 2616
. 2017-08-28 17:11:50.160 Handling network read event on socket 2616 with error 0
. 2017-08-28 17:11:50.160 Received 28 bytes (0)
. 2017-08-28 17:11:50.160 Read 4 bytes (24 pending)
. 2017-08-28 17:11:50.160 Read 24 bytes (0 pending)
< 2017-08-28 17:11:50.160 Type: SSH_FXP_STATUS, Size: 24, Number: 5394
< 2017-08-28 17:11:50.160 65,00,00,15,12,00,00,00,00,00,00,00,07,53,75,63,63,65,73,73,00,00,00,00,
< 2017-08-28 17:11:50.160 Status code: 0
. 2017-08-28 17:11:50.162 Listing directory "/mnt/user/Downloads".
After moving this single file, My Backup Share is now showing on the cache drive with this file in it.