[Bug] Export to pdf on Preview (Monterey)

Terrible that Apple changed this. A lot of people work with PDFs and need to "flatten" them after filing in a fillable pdf to pass it along to someone else who doesn't open it and have the same fillable forms. Tons of other uses. Preview used to be a good way to do this, allowing one to print or export to a PDF. Not sure why they broke this.

Using Safari to open the PDF, then "print to PDF" works. Same with Chrome. This flattens the output PDF, which is no longer secured (in my testing) and pages can be extracted, or edited in acrobat.

But it is a poor workaround.

Another solution I found:

• Right-click (or hold down Control and then click) the file and you will see this:

• Now click on "Duplicate" as shown above.
• It will be saved in the same location as the original PDF with the name [file name] copy.

Give this a try: boot into Safe Mode according to How to use safe mode on your Mac and test to see if the problem persists. Reboot normally and test again.

NOTE: Safe Mode boot can take up to 3 - 5 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 ⬅︎

The following has worked for me. (I have used uppercase for the main points.)

-     Before you do anything, consider copying the file to a new name, so you can keep the

original unprotected one. (You can delete it later if you want to.)

-      Open your pdf in Preview by right-click, select Open With, and choose Preview

-      In File menu of Preview, click on EDIT PERMISSIONS

-      On the dialog box, click on the square for Require Password to Open Document

-      Type and verify the password you are giving the file

-      Where you see Permissions, UNCLICK EVERYTHING

-      Type and verify the Owner Password, which can be same or different as the other one.

-      Click on Apply

-      Close the file (you don’t even need to Save)

-      When you want to use the file again, you can open it with Preview (though you don’t have

to) especially if you want to change permissions again.

 Hope this helps.

I've found a workaround for this:

• Go to the Finder and select the file and the 'Open with Safari'
• In Safari, "Print->Save as PDF" works for me for the protected files I've tested.

Until then I had to keep an old VM running Mojave to save protected files as PDF.

I have the same issue Print… > PDF > Save As PDF functionality is greyed out. I need to redact bank statements to file with the Court for some clients. I could not figure out how to make this work in Monterey on my new MacBook Air M1; worked previously on Big Sur with my old MacBook Air.

--> Found a work around, I placed pdf in Dropbox, then printed to pdf from the web browser Dropbox program on Firefox and saved to my computer; it stripped the security so that I can redact as I did previously.

I hope that they bring this functionality back. I reported it as a bug.

You cannot save a secure document: Option key + Save As, or Print… > PDF > Save As PDF

This option is greyed out in Monterey. Apple removed this functionality. Now I have no reason to use Preview.

The only way I can strip the security is by uploading to the web version on dropbox and printing as a pdf from there using Adobe Acrobat or Preview

I've done a test, print as PDF, export as pdf will grey out if you are attempting it on an encrypted pdf document. With the owner's permission (password), you should be able to print or edit or export certain pages and mix and match. Therefore i think it's not a bug, it's just a copyright feature enforced by apple.

Yes, someone suggested to print file but then print to pdf. This works like a charm.

My solution: I opened it in Safari, Print and finally Safe as PDF was available (very unelegant procedure, shame on you Apple ;-)

If someone sends me a bank statement, sometimes the are "secure" documents. In order to redact some information, the security needs to be stripped off/removed first. I work with multiple accounts, so I do not have time to store everyones' ever changing passwords. I previously, in earlier OS versions, would open it with preview and either "export to pdf" or "print; pdf." This functionality no longer works, as the commands are greyed out. The only work around I have found is to upload the document to dropbox, open it on the web browser (I use Firefox), then print to pdf from the browser. I also need this functionality to "print to pdf "only select pages I need. There are other reasons for this functionality, but Apple removed it, I think on purpose "for security reasons." It is ridiculous since it is still available on earlier OS, and on some windows. Just tripping up workflow on my new M1 Mac.

--> Found a work around, I placed pdf in Dropbox, then printed to pdf from the web browser Dropbox program on Firefox and saved to my computer; it stripped the security so that I can redact as I did previously.

There is a way to save it. Here's how:

• Right-click (or hold down Control and then click) the PDF and you will see this:

• Now, hover your cursor on 'Share' and you will see this:

• Click on 'Notes' and you will see this:

• Now it will be saved to the note you selected.

Thank you, but way too much time and trouble for the amount of docs I need to work with daily. Until Apple fixes this, I now open with Google Chrome, save as PDF and done. Hope that works for someone else.