[Bug] Export to pdf on Preview (Monterey)

The Preview in Monterey may not have the same functionality as in Big Sur because Apple can and often does change application functionality between operating system upgrades.

If you require your annotations in a separate PDF, and Export to PDF… is not working, then you still have Option key + Save As, or Print… > PDF > Save As PDF functionality. Just change the name of the new PDF in the dialog panel.

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.

Follow my steps on https://discussions.apple.com/thread/253311624?answerId=256850060022#256850060022 and then do the following:

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

• Now click on 'Get Info' and you will see this:

• Now click on the checkbox next to 'Locked' and a tick mark should appear inside it.
• This makes the duplicate read-only (not editable).

I'm having the same problem! I receive Docusign PDFs and with Big Sur I could "Export as PDF" separate docs and then combine them into one file (couldn't combine them without "Export as PDF" first). With Monterey I cannot do that, and I have not found a way to combine Docusign (or protected) PDFs into a single file - e.g. contract + addendums. I can export to a PNG, and then export that to a PDF but the new PDF shows the first page over and over - e.g. a 13 page doc will now be a PDF with the first page 13 times...

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 ⬅︎

If you haven't already, send feedback to the macOS product team, as they do not participate here and will never see the accumulated comments. And then there is convincing them that they have a problem to fix, an assigned priority, and some future Monterey Preview fixes cycle.

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

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.

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.

After even more research, it looks like annotation metadata has been included in files annotated by Preview as far back as 2013! Complete with the account display name of the macOS user who made the edits.

https://apple.stackexchange.com/questions/101452/remove-author-metadata-from-pdf-annotations-in-preview

You can view annotations in PDFs by going to Tools > Show Inspector > Annotations. Here is an old screenshot from 2014:

So it looks like the only thing new here is that Monterey allows you to edit annotations previously made, just by opening the PDF. In theory you can now edit annotations made as far back as macOS Yosemite (although I haven't tested it).

If you want to flatten the PDF, you can use Chrome to "print" to PDF. If you try to do the same with Safari, it will still include the annotation metadata.

Same problem, Chrome browser and Monterey BUT, I managed to "print as pdf" (I don't know about annotations). It is "Command+P", then chose "Print as PDF", then I clicked "More Settings" and chose the lower option "Open PDF in Preview", then "Print" and back down at the left appeared "PDF". Cliked the arrow down and "Save as PDF", chose the destination on the window that opened and then... THAT's IT, I could finally save the page I had opened in Chrome Browser as a PDF file.

This is a very annoying and confusing bug (if you can call it that way) in Monterey, because it includes the option but then you get stuck on that greyed out window with nothing happening, it's absurd. Or, Apple decided to make complex something that was and should be really quick and simple. I hope it works for you too.

Preview autosaves your changes and it is not a PDF Editor that will allow you to revise the original PDF text content. If you need that capability, there are several PDF editors in the Mac App Store and they are not free.