A wireless cryptographic fill system includes a fill device and a host portion. The fill device is configured to store one or more cryptographic keys and related data in memory therein. The host portion is coupled to a host processor, such as a secure radio configured to perform secure operations utilizing the cryptographic key. The fill device and the host portion are configured to communicate wirelessly with each other. Wireless communications may be accomplished optically, magnetically, inductively, capacitively, via radio frequency, or via bar codes. In one embodiment, the fill device is stylus-shaped, and is inserted into (or positioned proximate) the host portion to achieve wireless communications. In another embodiment, the cryptographic fill device is card shaped, and is inserted (or swiped) into a slot on the host portion to achieve wireless communications.