Context
My overall goal is to make a set of PDFs available, in such a way that users can be assured of the provenance of the documents (i.e., they came from the origin that they are expected to come from). I'm thinking about doing this by digitally signing the PDFs on the server. These signatures won't be in risk of expiring, because the server can just reissue new signed PDFs when the certificate is updated. Using SSL to serve the documents wouldn't be enough, because the files can be passed on to third parties, who don't want/need to access the server.
Problem
The expiration issue arises because some of these PDFs will already have one or more digital signatures (e.g., created for legal purposes). My question is, if the server signs the PDFs, will it also be ensuring the continued validity of the previous signatures, even after they expire, as long as the latest signature is valid?
I'm asking more on the theoretical side, although I plan to implement what I describe using iText, so any pointers on how to use it for my purpose are also welcome.