OS X Big Sur print, "Save As PDF" not an option!

I am a full time REALTOR® and use the "Save as PDF" function daily when printing documents. Now with the OS X Big Sur update, if the document is protected, I can no longer use the Print, "Save as PDF" function. I have an older MB Pro (Catalina) and that function is there no matter if the document is protected or not. DOES ANYONE HAVE A SOLUTION? I need to SEPARATE PDF's on a regular basis or MARK THEM UP (even protected documents that I don't have the password to) and the old OS Catalina did this just fine. Big Sur, does not work.

Posted on Nov 15, 2020 8:12 AM

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63 replies

Nov 15, 2020 2:57 PM in response to dkazreal

Boot into Safe Mode (How to use safe mode on your Mac - Apple Support) by booting with the Shift key held down and check there to see if the problem persists.  Reboot normally and test again.


NOTE: Safe Mode boot can take up to 10 minutes as it's doing the following; 

• Verifies your startup disk and attempts to repair directory issues, if needed

• Loads only required kernel extensions (prevents 3rd party kernel/extensions from loading)

• Prevents Startup Items and Login Items from opening automatically

• Disables user-installed fonts 

• Deletes font caches, kernel cache, and other system cache files


Nov 15, 2020 7:20 PM in response to dkazreal

When one password protects any document on the Mac, the usual interface for that also provides an optional remember the password in Keychain choice. If you selected that, you will never be challenged for a password while in your own account, and in that scenario, the document automatically unlocks, and the Print : PDF : Save as PDF would behave normally and as you expect.


If you did not check that remember this password in Keychain option when applying a password to a document, or were attempting to open a document that another user set the password on, then the operating system security, whether Mojave, Catalina, or Big Sur will challenge you for the password — before the Print… menu item would be made available to you.


If you open a PDF that has been encrypted with a password, and without that password being registered with Keychain, then you can do nothing to that PDF in Preview without entering the password.


I thoroughly tested this again this evening with the same document (and encrypted PDF) on Mojave, Catalina, and Big Sur — before my previous post, with and without Keychain password resolution, and I stand by this content, and my previous post. You must unlock the document before it the Print panel can be accessed, or a PDF can be annotated.

Dec 3, 2020 2:40 AM in response to dkazreal

This may have to do with these specific pdf files.


FWIW, I have NO problem printing to pdf, AND selecting pages - e.g. choosing "selected pages in Sidebar" when using "Save to PDF". It is all working, with pdf files that require password for printing and/or for opening.


I am not a realtor, and of course I have no access to the exact sort of document being discussed. Probably they are encrypted at the source in a particular way that is causing problems.


It might help if you could arrange for one sample document (of course, not containing private information) encrypted in the same way as those you are using, so we could test.

Nov 15, 2020 2:35 PM in response to dkazreal

That Print… PDF : Save as PDF menu entry will be inactive until you successfully fill in the password prompt for the encrypted document. If this is for instance, a password protected Pages v10.2 document on Catalina 10.15.7, the Print and Export To menus are absolutely inactive in Pages until the document password is provided. I also tested this on Big Sur with the same Pages document opened in Pages v10.3.5, with the same restrictions as on Catalina.


The preceding paragraph works the same way, on both macOS platforms, with password protected PDFs that are opened in Preview, where you can do nothing without first applying the document password to the PDF to unlock it.

Dec 2, 2020 3:50 PM in response to dkazreal

I use this feature daily for work as well.


Just to get a couple things out of the way. Answers suggesting other software are not helpful when we are talking about a feature that used to work and now doesn't. Also all the password talk is irrelevant to this particular issue. I also have an older Catalina machine, the PDF allows me to markup or exact pages using the "save as pdf" option in the print dialogue box. The Big Sur machine does NOT allow this.


Here's why this is completely unacceptable. I can literally print out the pdf on paper, do whatever I want to it, scan which ever pages I want, back into pdf form. Or as someone else suggested, export as pdf, find and open THAT doc, mark up, and then save as pdf with the pages I need. Protected or not, this worked in the past, now it doesn't. Apple isn't protecting us from anything since the above two methods will accomplish the same thing. This is why the password answers don't apply.


I'm calling Apple now to hopefully get some help on this.



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OS X Big Sur print, "Save As PDF" not an option!

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