Reliability mechanisms for a connection can be selectively implemented based on the type of USB device that is redirected over a remote session. When a client attempts to redirect a device over a remote session, an agent on the server can be configured to detect the type of device that is being redirected. If the device is a mass storage device that implements the SCSI standard, and if a connectionless datagram protocol is employed to establish the connection, the agent can implement some reliability mechanisms such as reordering and windowing but not the recovery of lost packets. In contrast, if the device does not implement the SCSI standard, the agent can implement each reliability mechanism including the recovery of lost packets.