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https://issues.apache.org/jira/browse/PDFBOX-2729?page=com.atlassian.jira.plugin.system.issuetabpanels:comment-tabpanel&focusedCommentId=15087988#comment-15087988
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Tilman Hausherr commented on PDFBOX-2729:
-----------------------------------------

The encryption object is created in PDFParser.prepareDecryption(), has the 
encryption key, and is then "lost". The solution will be to pass this object to 
the PDDocument object that is created later.

> Can't sign encrypted PDF files
> ------------------------------
>
>                 Key: PDFBOX-2729
>                 URL: https://issues.apache.org/jira/browse/PDFBOX-2729
>             Project: PDFBox
>          Issue Type: Bug
>          Components: Signing
>    Affects Versions: 2.0.0
>            Reporter: Cyril Bremaud
>            Assignee: Andreas Lehmkühler
>         Attachments: Scan0001.pdf, Scan0001_protected.pdf, 
> Scan0001_protected_signed.pdf, Simple-128-bit-encrypted_signed.pdf, 
> Simple-256-bit-encrypted_signed.pdf, Simple-40-bit-encrypted_signed.pdf
>
>
> It is not possible to sign an encrypted PDF document.
> More details here :
> [http://stackoverflow.com/questions/29232684/signing-an-encrypted-pdf-document-with-pdfbox-2-0-0]



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