If a network device connected to an Apple computer is not uploading the selected files/folders to the cloud, there may be a protocol barrier. Check to see if the connection to the network device is listed as using afp (AppleTalk Filing Protocol). If it is, you will want to disconnect (eject) that network device and reconnect it using smb (Session Message Block (pronounced Samba)) protocol.

To check on the connection, right-click the network device in the side-bar of a Finder window and select Info. Make sure the General section is expanded. If it is an afp connected network device, the first line will read something along the lines of Server: afp://SharedNAS

If it is an afp connected device, disconnect it by pushing the eject button to the right of the network device's name in the side-bar of Finder. At that point press command+K in Finder to bring up a network connection window. In the text field type smb://[Path to Network Device] and press Connect. Once reconnected, redefine the folder path in OBRM and retry the upload.

Note: Changing the connection protocol may affect other applications. Most applications that are available on both Windows and Macintosh will not have trouble communicating over smb. If there is an Apple-Only application, you will want to test it to make sure it functions correctly.