Systems and methods are described for over-encrypting symmetrically pre-encrypted content for off-line delivery to playback devices using portable media drives in accordance with embodiments of the invention. One embodiment of the method of the invention includes symmetrically pre-encrypting the content, receiving a request to issue content for playback on at least one playback device associated with a user account, where each playback device includes a processor containing a private key assigned to the playback device by a conditional access system, generating a content key and over-encrypting at least a portion of the symmetrically pre-encrypted content in response to the request, obtaining a public key for each playback device, encrypting a copy of the content key using the public key of each playback device associated with the user account, and delivering the over-encrypted content and the at least one encrypted copy of the content key to a playback device associated with the user account.