Mike,

Please search the archives for "deferred signing".

In a nutshell: the time of pdf stamping is included in the signed pdf. Thus,
each time you create a stamper for signing, the hash of the bytes to sign is
different.

Some ideas on how to get around this problem have been presented on this
list. Additionally a rewrite of the itext signing code had been promised,
maybe it will support deferred signing out of the box.

Regards,   Michael

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