Content-based addressing is used to navigate forward, backward and in a circular fashion through documents in a content space. To enable backward navigation, a descriptor file is created for a new version that contains not only a message digest for the new version, but also a message digest of the older document. A message digest is created for the descriptor file. A user navigates backward starting with the message digest of the descriptor file. To enable forward navigation, a mapping table maps a message digest of an older document into the message digest of the new version. A high-level descriptor file contains the message digest of the original document and the message digest of the mapping table. The message digest of the high-level descriptor file is returned to the user. A user navigates forward starting with the high-level descriptor file message digest. To enable circular navigation, a mapping table maps a message digest of a second document into a message digest of a version of the second document containing a message digest of a first document. The techniques are combined to allow navigation through a complex content space.