Best way to annotate a PDF in Preview using Apple Pencil?


I open a PDF in Preview on the Mac (Monterey on M1 MBP) and would like to go from Preview to my iPad Pro to mark it up with freehand annotations using the Apple Pencil, then send back to Preview.

I have lost track of the iterations of moving from Preview to iPad, but the only current option I see is in the Windows Menu “Move to iPad Pro” - this gives the Sketch tool on the iPad, which includes shape detection, which I most definitely do not want. I want to circle, underline, write words, cross stuff out in freehand, just like you would pencil and paper.

How are you all doing this?

You can do freehand edits that way by tapping on the markup toolbar icon (circle with pen) and then tapping on the “Draw” icon. It’s a bit clunky, since it uses the Apple pencil to manipulate the Mac environment, displaying the cursor. To undo an annotation, you need to select the “undo” menu item on the Mac.

Another option: there’s a feature “continuity markup” described here. From Finder, select PDF file, press space bar to preview, then tap on pen icon. This provides an iPad like interface similar to iPad notes.

I prefer to annotate with PDF Expert on the iPad, so I save the PDF to iCloud on the Mac, and open within the PDF Expert app on the iPad.


I use Books.

You can save a copy of your PDF to Books on your Mac, mark it up (in Books) on your iPad, then drag a copy of your PDF out on your Mac.

Make sure you are logged into Books so the files will sync via iCloud. Use the three dots menu on the lower right of the PDF file to remove it completely from Books.

I’ve never tried using the Books app for this purpose. Our highlights available to be extracted in the Books app?

I’m not aware of any way to export highlights. I only use Books for PDFs & epubs like the Take Control series.

I use the Kindle app for nonfiction reading. I highlight with the Apple Pencil and copy the highlights file from my paperwhite kindle when I’m finished.

Not only did I forget about this, I forgot about the Keyboard Maestro macro I made a few months ago to deal with this exact issue by opening the front document from Preview in Finder then trigger Continuity Markup. Doh!

Thanks for the reminder.


I just opened a book that had highlights. I was able to go to the “notes” view, command-click on each note and then from the share context memo send the notes (with location data, etc) directly to DevonThink.

I didn’t realize it could do this either. Nice. Since most of my note taking if from books, this will work well to move references into DevonThink.

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That’s intriguing, I’ll have to give this a try. Thanks for posting!

How about setting up the Mac and iPad with Sidecar? The iPad would be an extended monitor. Just drag the pdf document to the iPad screen and use your Apple Pencil to annotate. I’m thinking that would work?

I’ve seen my daughter use goodnotes on her MacBook and dumps PDFs tthere. Then have it sync to her iPad for markup and annotations. That might be another idea

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Yep, this works as well. Thanks!

In most cases, I prefer something I can do immediately from within Preview since that is usually where the PDF will start in the course of normal work. Although I do prefer to markup in PDF Expert like @ehpehp - if I know I am going to doing markup I might start there.

For anyone interested, here is the KM macro for my use case, which is sending the current front document in Preview to the Continuity Markup feature, which makes the “Draw” tool available so you can draw without shape recognition, and you can easily send to iPad/iPhone.

AppleScript bits:

tell application "Preview" to set thePath to path of front document
set theFile to POSIX file thePath
tell application "Finder"
	reveal theFile
end tell
tell application "System Events"
	tell process "Finder"
		tell window "Quick Look"
			set theGroups to every group
			repeat with i from 1 to number of items in theGroups
				set theButtons to every button of item i of theGroups
				repeat with i from 1 to number of items in theButtons
					set ButtonDescription to description of item i of theButtons
					if ButtonDescription is "Annotate document" then
						click item i of theButtons
					end if
				end repeat
			end repeat
		end tell
	end tell
end tell