This application describes methods and systems of performing digital asset management. In one implementation a method of determining whether content should be encrypted when the content is found in an unencrypted form is provided. The unencrypted form of the content includes a digital watermark embedded therein including a message. The method recites: decoding the digital watermark from the encrypted form of the content to obtain the message; based at least in part on the message, determining whether the unencrypted form of the content should be encrypted; and if so decided by the determination, encrypting the unencrypted form of the content. Other implementations and embodiments are provided as well.