This is possible, how difficult depends on how the PDf is attached. If the users are just going to attach it to the communications tab on the SO, then you'd need a script to append it to the PDF. If it's selected in a custom Document field on the SO, you may be able to just do it from within the PDF itself using <pdfset> - that allows you to combine PDFs. So you'd do <pdfset><pdf> {all your regular pdf stuff] </pdf> <pdf src = ${your custom field link to the other PDF} /> </pdfset>