MacOS – How to print and email PDF from any OS X application on PDF letterhead

For a free and universal alternative you can use the pdfbook script, part of the pdfjam collection which is usually included in LaTeX distributions (notably MacTeX). It's simple to use from the command line:

pdfbook mypdf.pdf

If the above doesn't work, then /Library/TeX/texbin isn't in your PATH (or /usr/texbin for older versions of MacTeX). The best course of action is to ensure PATH is correctly set (lots of command line programs will fail if the PATH variable isn't correct and pdfbook is one of them); this isn't trivial under OS X if you want a consistent behavior between applications launched from the dock and applications run from a terminal so you definitely should search a complete solution to this specific problem. As dirty work-around, you can run export PATH="$PATH:/Library/TeX/texbin:/usr/texbin" every time before you use pdfbook (including in the service below).

If you don't want to use the command line, you can create a service easily.

1. Launch Automator (on Yosemite it's in Applications/Others)
2. Create a new document and select "Service".
3. On top of the right frame, for "Service receives selected" choose "PDF files".
4. Search "Run Shell Script" from the bar on the top of the left frame and double-click it. Select to "Pass input" as "arguments" in the newly created window.
5. Enter a simple script running pdfbook, for instance pdfbook "$@".
6. Save it as "Create booklet" (for instance).
7. In Finder, select a PDF file, then in the menu go to Services/Create booklet.

My complete script also creates a temporary file and opens the resulting PDF:

TMPF=`mktemp -t bookletXXXX`
mv "$TMPF" "$TMPF.pdf"
pdfbook -o "$TMPF.pdf" "$@"
open "$TMPF.pdf"

The most obvious problem is the several GB download and installation of a LaTeX distribution if all you want is the pdfbook script.

Adobe Reader 10.x does go out of it's way to hide the normal print options from OS X but you can still get to them by clicking on the Printer... button at the bottom of the Adobe Print Dialog and clicking through the warning not to change things behind Adobe's back.

I don't have a form like you mentioned in red, but try setting all the print options in Adobe to make your form appear as desired (with or without stamps, annotations, sticky notes and summaries, etc...) and then get to the Apple print dialog to attempt a print to PDF.

If Adobe isn't preparing the file for print until after you hit print in the Adobe dialog - then your only recourse is faking it out by defining a new virtual printer. That way adobe is forced to send the data to the mac which will then pop it into a plainer PDF file for you with just the data filled out.

I've not resorted to this, but CUPS-PDF and this tip on making it work with Snow Leopard's sandboxing security looks to be promising. I hope you don't have to resort to that hacky of a solution to save paper waste and time.