Techniques for facilitating communication between a portable media device (PMD) and an accessory via multiple communication paths. In one set of embodiments, an accessory can be coupled with a PMD via a first connection, thereby establishing a first control communication path. The accessory can send to the PMD, via the first control communication path, an enumeration of the communication paths supported by the accessory. The enumerated communication paths can include control communication paths and data (e.g., audio or video) communication paths. The accessory can further send, to the PMD via the first control communication path, an availability status of each data communication path. In response, the PMD can select, based on a routing policy, one or more of the data communication paths and can notify the accessory of the selected data communication path. The PMD and accessory can then interoperate by exchanging data signals over the selected data communication path.