If a network device connected to an Apple computer isn’t uploading the selected files or 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 so, you’ll want to disconnect (eject) that network device and reconnect it using the SMB protocol.

To check 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 the network device is connected via AFP, the first line will read something along the lines of Server: afp://SharedNAS. Disconnect the device by clicking 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 the network connection window. In the text field, enter smb://[Path to Network Device], and then click Connect. Once reconnected, redefine the folder path in OBRM and retry the upload.

Note: Changing the connection protocol may affect other applications. Most applications available both in Windows and macOS won’t have trouble communicating over SMB. If there’s a macOS-only, you’ll want to test it to make sure it functions properly.