For PDFs I have had good success with CutePDF.
It simply shows up as a printer.
Just 'Print' to that printer option and things seem to always work.
It pops up, asks where to save the pdf, and 'prints' it to a pdf file.

Of course, your mileage may vary, but it has been a nice option here for years.
http://www.cutepdf.com/


I do not work here, but the benefits are still awesome
Make your sound your own!