How to password-protect a PDF before e-mailing in OS X

How to password-protect a PDF before e-mailing in OS X

With a few steps you can set up an easy way to encrypt PDF files generated from the standard print dialog window.

The print-to-PDF feature in OS X is convenient for quickly preserving
a document’s layout in the PDF format, so it can be viewed on most
computers and tablets. If you would like to send someone a formatted
document that contains sensitive information, you may want to add the
step of protecting it with a password.

To do this, you can use a container format such as a ZIP file or an
encrypted disk image (using the Disk Utility program in OS X); however,
these may be a bit cumbersome to manage, both for the sender and

An alternative is to send the PDF as an encrypted PDF file with a
password that must be entered by the recipient before the PDF can be

After choosing Print to PDF and opening in
Preview, save the document
and click
the Encrypt option (circle). Then send
the encrypted PDF using

 the Share button (arrow) as an e-mail

There isn’t a specific option to print a document to an encrypted PDF format in OS X, but the procedure is simple enough:

  1. Use the PDF menu in the print dialog box and choose “Open PDF in Preview.”
  2. Press Command-S to save the PDF.
  3. In the save dialog box, click the “Encrypt” check box and provide a
    password for the PDF, and then save it to your desktop (or similar
  4. Now click the Sharing toolbar button in preview and choose the Email option.

This action will create the encrypted PDF and offers a relatively
easy way to attach it to a new e-mail message. However, if you use this
feature regularly then you may want a slightly more streamlined

Luckily, OS X supports an option for custom print plug-in workflows
that you can use to encrypt a PDF directly from the PDF menu in the
print dialog window. To do this, open the Automator program (in the
Applications folder) and follow these steps:

When creating the workflow,
 for the encryption action be sure
 to check
the option to show the
 action’s input when the
 workflow runs (click for
larger view).
  1. Create a new workflow.
  2. Select “Print Plugin” as the type of workflow to create.
  3. Locate the “Encrypt PDF Documents” action and drag it to the workflow area.
  4. Click the Options button for this action and check the option to “Show this action when the workflow runs.”
  5. Locate the “New Mail Message” action and drag it to the workflow,
    below the encryption action (you can optionally use the “Add Attachments
    to Front Message” action, or have this in a separate workflow

Save the workflow with a name like “Mail Encrypted PDF” and you
should be good to go. Now whenever you print a document you can choose
this workflow from the PDF menu and after you supply the password to
use, the system will generate the secured PDF document in a new e-mail


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