Receiving a PDF in OS X Mail, marking it up, and sending it back

I can do this easily enough in iOS. In OS X, I have to hit "forward" and send the email back to the person. Then, if I hover over the PDF, there is an option to mark it up. Is there not a simpler way? In iOS, I just long press the PDF and I get the option "mark-up and reply". Is there not a similar feature in OS X?


ChatGPT actually told me this:


You can annotate PDFs directly within the Mail app on Mac OS X by using the built-in Markup feature. Here's how:

1. Open the email containing the PDF attachment in Mail.

2. Right-click on the PDF attachment and select "Markup" from the context menu.

3. Use the tools in the Markup window to annotate the PDF as needed.

When you're done, click the "Done" button to save your changes and attach the annotated PDF to a reply email to the sender.

Compose your reply email, add any additional text or attachments, and hit the "Send" button to send your reply with the annotated PDF attached.

Except there is no "Mark-up" from the context menu. Though I would think there would be. Any ideas?

Posted on Feb 3, 2023 7:31 PM

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2 replies

Feb 4, 2023 1:39 PM in response to Randall_2023

Thank you for the reply. I’m familiar with how to get the PDF into preview to mark it up. But that is a ton of extra steps, especially if I want to get the pdf back into the original email to reply to it.


iOS allows me to long press a PDF from a sender *in* Mail. Then mark up. Then I just hit “Done” and the OS replies to the sender with their marked up PDF.


As it turns out, I learned in Ventura that if I set OS X mail to include attachments in reply, I can reply to the sender and then I have the ability to mark up the PDF directly in Mail. But now, every single email includes attachments in reply. That’s unnecessary. I can set the OS to ask me every time, if I want to include the attachments, but that’s pretty annoying.


Prior to Ventura, if I FORWARDED the email back to the sender, the OS would include the attachment. Then i could mark it up. That worked. But I just couldn’t shake the feeling, since it was so simple to do reply in iOS and mark up a PDF (without this “forward kludge) AND this has to be something people do all the time, that there must be a way to do this on the desktop OS also without having to do this “forward” work around. And that I was missing something.


Now in Ventura, the forward work-around doesn’t work. It just seems very strange to me this functionality for something so common, isn’t more elegant.


P.S. The use case is someone sends me a PDF, I want to sign it and send it back. So easy on iOS. Not so easy on the desktop OS. So I figured I’m just doing it wrong.

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Receiving a PDF in OS X Mail, marking it up, and sending it back

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