Removing a PDF Password in Monterey

It used to be easy to remove a PDF password. Open the file in Preview, Export As PDF and you're done! Since upgrading to Monterey, "Export As PDF" is now greyed out when you have a PDF file open. Is there another way to remove a PDF Password using MacOS built-in tools? (I know I can do it with PDF Expert, but would like a method that works without 3rd party apps.)

MacBook Air (2020 or later)

Posted on Oct 28, 2021 9:43 AM

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Posted on Nov 4, 2021 11:54 AM

I just ran another test with Preview Version 11.0 (1033.2) on a PDF file that I protected with a password:


1 - doing a File ➙ Export without a password assigned gave me a password protected file with the same original password.


2 - doing a straight Print ➙ Save as PDF gave me a password free PDF file.


Note: I'm running the latest beta Monterey. Why it didn't do the same 2 days ago when I first did my test (same versions) and the shortcut I don't know.

100 replies

Oct 29, 2021 9:06 AM in response to Luis Sequeira1

Thanks for all your insight ... but the thing is ... I have e-mails from before Monterey, mostly all from the same set of senders, which worked perfectly with a simple "Export as PDF" option in the file menu. I tried those same PDFs out of my Mail Archive, and "Export as PDF" is greyed out on those same files in Monterey. So the documents are still being created exactly as they were before. It is the way Preview in Monterey works with them that has changed, and not the documents. Hopefully Apple will treat this as a bug and fix it, and soon.

Oct 30, 2021 10:18 AM in response to harald163

harald163 wrote:

Same problem since upgrading to Monterey. But it seems not to be a password protection issue. Export as PDF is always greyed out, even on a freshly created and unprotected PDF file. Looks more like a bug than a feature.

Yes you're right. I hadn't noticed because I only use this export feature to remove passwords from protected PDF files.

I reported a bug at Apple's https://feedbackassistant.apple.com. I suggest anyone else who cares about this issue do the same.

Nov 2, 2021 12:44 AM in response to lp1756

Have the same problem.

•  Since installing OS Monterey (12.0.1) opening a password protected PDF with password and ‘Printing to PDF’ (or ‘Export as PDF’) delivering a new PDF without password is no longer available; ‘Printing to PDF’ and ‘Export as PDF’ is grayed out;

•  To exclude the possibility the sender’s PDF protection has changed, I tried the same ‘Printing to PDF’ and ‘Export as PDF’ operation with the identical password protected PDF on a different Mac (OS Big Sur 11.4). In both instances it delivered a new PDF without password, so the cause of the problem seems to be Monterey.

•  Is Apple working on it or should I reinstall Big Sur?

Nov 2, 2021 10:49 AM in response to lp1756

lp1756 wrote:


Old Toad wrote:


Gijs Kijlstra wrote:

H so the cause of the problem seems to be Monterey.
It looks like Apple plugged a security hole instead of it being a bug.

What good is password protecting a PDF document if anyone can bypass the protection with a Print to PDF.
Here's the use case -- I get a monthly invoice that is password protected. I like to save the files away but do not want to keep a database of passwords used to open these files. I have been given the password for this file so now I feel I have the right to read and save it unencrypted so that I can read it anytime I want. Five years from now I'll still have the file, but where will the password be? I think the utility had the intention of protecting the invoice from prying eyes on the internet but had no desire to protect the file once I saved it from my email. We're not talking government classified documents -- we're talking light weight privacy protection. So what is wrong in this case with me removing the password on an invoice sent to me by my electric utility? The Export as PDF feature did not work unless they had the password. I don't really see that as a security hole.


I see how your use case makes sense.

The thing is how the utility may have encrypted this pdf.

I can attest that with the password protection created on the mac (not using any Adobe software), once the pdf is open it CAN be saved without a password.

Oct 28, 2021 10:37 AM in response to lp1756

Very strange that a password protected pdf could be saved without password. If something is wrong that is not in Monterey. This said, we know that password protection of pdfs can be made by several apps but I believe that if a pdf is generated by Adobe Acrobat Pro/Distiller surely there's no way to bypass it.

And also, password are for viewing and/or saving and/or printing. Depends what the password is there for.

In any case I would try to remove it via web. Some sites promise to able to do it but I never tried so I can't assure they'll work.

Sorry for just teory, I din't have my Mac with me neither a three level Adobe PDF protected to experiment. If you need I'll do.

Oct 28, 2021 10:42 AM in response to majortom1967

majortom1967 wrote:

Very strange that a password protected pdf could be saved without password. If something is wrong that is not in Monterey. This said, we know that password protection of pdfs can be made by several apps but I believe that if a pdf is generated by Adobe Acrobat Pro/Distiller surely there's no way to bypass it.
And also, password are for viewing and/or saving and/or printing. Depends what the password is there for.
In any case I would try to remove it via web. Some sites promise to able to do it but I never tried so I can't assure they'll work.
Sorry for just teory, I din't have my Mac with me neither a three level Adobe PDF protected to experiment. If you need I'll do.

You are right. I've always thought it strange that it was so easy to remove a password from a PDF. Nevertheless, until I upgraded to Monterey the Preview Export as PDF method I described above worked just fine. If you google "mac remove pdf password" you'll find dozens of sites describing this method.

Oct 28, 2021 12:24 PM in response to lp1756

There are different levels of “protection” for a pdf. If one only gives it a password to open, then everyone with the password should have unfettered access to it - not unlike if you encrypt your drive with FileVault you can still access your files for reading and writing once the drive is unlocked.

Now a pdf may be explicitly created so as to prevent printing, for example, or copying (though for full functionality you’d need Adobe Acrobat).

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Removing a PDF Password in Monterey

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