An information handling system and keyboard automatically coordinate wireless pairing when the keyboard couples to the information handling system to interface contacts exposed at the information handling system housing and the keyboard. The information handling system retrieves an identifier of the keyboard through a contact, determines if the keyboard is already paired, and if not initiates wireless pairing with a command through the contact. A pairing key is provided from the keyboard to the information handling system through the contact and applied by the information handling system to complete pairing. A confirm code is communicated through the contact to the keyboard for communication back to the information handling system by wireless signals. The contacts provide a charging path to charge the keyboard when coupled to the information handling system.