A stackable connector interface with magnetic retention for electronic devices and accessories can allow power and data to be transferred between one or more stacked connectors. Each interconnected stackable connector may include one or more magnetic elements, which magnetic elements may have poles arranged to facilitate mating with other stackable connectors. The magnetic elements may also provide a magnetic retention force that holds mated connectors in contact with each other. The connectors can also include connection detection circuitry for determining whether the connectors are mated with other connectors, thereby allowing the connectors to prevent live contacts from being exposed at an unmated surface of the connectors. In addition to connection detection circuitry, routing circuitry may also be included to determine how signals should be transferred between the interconnected stackable connectors and/or corresponding devices.