Six Colors
Six Colors

by Jason Snell & Dan Moren

Support this Site

Become a Six Colors member to read exclusive posts, get our weekly podcast, join our community, and more!

By Dan Moren

Quick Tip: Export encrypted PDF without a password in Monterey

Oh, tax season. Admittedly, the annual ritual has gotten a lot easier for me since getting a) an accountant and b) getting most forms delivered electronically as PDFs.

But I ended up with a wrinkle this year when I was processing a few of the tax forms provided by my clients. Several of them used a handy service that emails tax forms, which also thoughtfully encrypts and password protects those files. However, when uploading these for my accountant, I find it convenient to strip out the protection, so that I don’t have to provide a bunch of passwords as well.

In the past, I’ve simply used the loophole of opening a PDF in Preview, entering the password, and then using the File > Export as PDF… command or the old trick of printing to a PDF. That generates a version of the file without the password protection.

No exporting protected PDFs

However, in macOS Monterey I was surprised to discover that these loopholes have been plugged. Exporting as a PDF simply maintained the password protection, and trying to save as as PDF from the Print menu wasn’t even an option: the system now grays it out.

In theory, this is a good security practice to avoid having password protected files easily stripped of those protections.1 But when it comes to my personal usage, it’s decidedly inconvenient.

But it turns out, whoops, Apple didn’t implement these security features across the board. Making an end-run around these restrictions is as easy as firing up your web browser. I used Chrome for my first foray, but I then tested the same process in Safari, and it works just as well.

Just open the password-protected PDF in your browser of choice, enter the password, and then print to PDF just as you would have in Preview (or even just open an unencrypted copy right in Preview). I was then able to save a password-free version.

All of this is a bit silly: there’s really no point in locking down Preview if all you need to do is use another app. Then again maybe this loophole will itself get plugged in another five years or so.


  1. Of course, you still need the password, so just how much this is actually a security loophole is questionable. 

[Dan Moren is the East Coast Bureau Chief of Six Colors. You can find him on Twitter at @dmoren or reach him by email at dan@sixcolors.com. His latest novel, The Aleph Extraction, is out now and available in fine book stores everywhere, so be sure to pick up a copy.]

If you appreciate articles like this one, support us by becoming a Six Colors subscriber. Subscribers get access to an exclusive podcast, members-only stories, and a special community.


Search Six Colors