Methods and systems for performing one or more path selection processes that determine connection conditions and send the data via established, multi-path, connections are described herein. The one or more path selection processes may be performed in a remote computing environment where the established, multi-path, connections are between two endpoint devices and are available to communicate data for a remote application and/or a remote desktop. Based on the one or more path selection processes, data for the remote application and/or the remote desktop may be sent via a connection that differs from connection assignments that were configured when the connections were initially established. Additionally, as part of the one or more path selection processes, routing information that indicates a routing path may be inserted into data sent via the connections. An intermediary device may be caused to route the data according to the routing path indicated by the routing information.