How to mark up a PDF attachment in Apple Mail on Mac: steps and fixes

What you need before you start

You need Apple Mail on a Mac and a PDF attached to the message you are writing. The steps work in the compose window, the editor you use for a new message. If the PDF is not attached yet, attach it first.

Apple publishes one procedure for this task. The copy you can read on Apple's site is written for macOS 27 Golden Gate, and the macOS Tahoe 26 version gives the same steps. Apple does not say which Mail versions the steps cover, so compare your screen with the steps below before you begin.

If you are not sure where to attach a file, the attachment guide walks through that step. Come back here once the file sits in the message.

Open Markup from the Action pop-up

Hover your pointer over the PDF in the message body. Apple's guide says to hover over an image or PDF in your message. A small Action pop-up appears in the attachment's upper-right corner. Click it, then choose Markup.

The Markup toolbar opens, and the PDF is ready for marks. Everything happens inside the message, so you never leave the compose window to mark up the file.

The pop-up is small, and it shows only while your pointer is over the file. If you move the pointer away, it disappears. Hover again and it returns. Move slowly if you have trouble catching it on the first try.

Walk through a real markup pass

Say you are sending a rental agreement to a tenant. You want to flag one clause, write a note beside a date, and add your signature at the bottom. Attach the PDF, hover over it, and open Markup from the Action pop-up.

Start with the clause. Choose Highlight Selection, then select the text you want to flag. Next, pick Text, click in the margin beside the date, and type a short note. Keep the note brief, because the tenant reads it at normal size.

Finish with the signature. Choose Sign and place your signature at the bottom of the page. Drag the blue handles if it needs to be smaller, so it matches the other text on the page.

Then click Done. Reread the page at normal size. A note that looked clear when you zoomed in can crowd the margin once the page is back to its usual view. This is the most common reason a markup looks fine on screen and wrong in the file.

What each Markup tool does

The toolbar holds a long row of tools, from Sketch to Annotate. Most people use only a few of them on a PDF. The table lists the tools Apple names and what each one is for in practice.

Draw is the one tool that depends on your hardware. It appears only on Macs with a Force Touch trackpad. If you do not see it, Sketch and Shapes cover most markup needs.

Resize, duplicate, and place your marks

Each markup item has blue handles. Drag a handle to resize the item. To make a copy, press and hold the Option key while you drag. This saves time when you need the same box or checkmark in several spots.

Placement matters more than people expect. Recipients see the marks as part of the PDF, so a label floating in the margin can confuse them. Put each mark right next to the text it refers to.

Rotate Left and Rotate Right help when a scanned page arrives sideways. Apple's guide also mentions Option-click on Rotate Right. Test that on a sample page first, so you know what it does before you rely on it.

Click Done, then keep editing until you send

Click Done when the markup looks right. Done closes the editing view, but it does not end the job. Apple says you can keep changing annotations until you send the message.

Reopen Markup from the Action pop-up at any time before you send. Each time you open it, you can move, resize, or delete marks. The file does not lock until the message leaves your outbox.

Check the marked-up PDF before you send

Read the message text and the marked-up page together. Many errors show up only when you read the whole message in one pass. Use this short checklist before you press send.

1. Read every page of the PDF at normal size, not only the page you marked.
2. Confirm each note sits beside the text it describes.
3. Check that the signature is on the right page and at the right size.
4. Look at the attachment size, and watch for a Mail Drop prompt.
5. Reread the cover note and make sure it names the correct file.

When the file matters, open the PDF from another device after you send a copy to yourself. Check each mark once more. This takes a few minutes and catches a shifted label before a client or tenant sees it.

When the Action pop-up does not appear

The most common cause is a setting that is turned off. Open System Settings, then go to General > Login Items & Extensions > Extensions > By Category. Click the Info button next to Actions, then turn on Markup. You change this setting once, not for every message.

After you turn it on, open the message again and hover over the PDF. If the pop-up still does not show, confirm the file is attached to this message and not linked from elsewhere. Then hover again.

Mark up a PDF you received in Apple Mail

The Action pop-up works on attachments in a message you are composing. A PDF someone sent you is a different case. Apple's guide to viewing attachments says you can select the attachment and press the Space bar to preview it.

To mark up a received file, Control-click it, choose Open With, and pick Preview for a PDF. Mark up the file in Preview, save it, and then attach the saved copy to a new message. Mail saves attachments to Downloads by default. To change that folder, go to Mail > Settings, click General, and pick another folder.

Apple's What's new page for macOS 27 lists no changes to attachments, Markup, PDFs, or the compose window. So the Preview route is not a new feature. It is the same idea with a different starting point.

Insert a drawing into the message body

Sometimes a sketch belongs in the text, not in a file. Control-click anywhere in the message body and choose Insert Drawing. The drawing goes into the message itself, not into an attachment.

Use this for a quick diagram or a rough layout. Use the PDF route when your recipient needs the original document, with its own pages and formatting.

When the marked-up PDF is too big to send

A marked-up file can grow, especially after you add a scanned signature or large images. Apple says you can send attachments up to 5 GB with Mail Drop. Those attachments do not count against iCloud storage, and Mail Drop works in the Mac Mail app.

Apple gives no specific number for the normal attachment limit. Instead, Mail prompts you to use Mail Drop when a message is larger than your Internet Service Provider's limit. Watch for that prompt after you attach the marked-up file.

Common mistakes with PDF markup in Apple Mail

• Marking up the only copy. Annotations become part of the file, so keep the original.
• Treating Done as the final step. You can keep changing marks until you send.
• Searching for a keyboard shortcut to open Markup. Apple's guide lists none.
• Expecting Draw on every Mac. It needs a Force Touch trackpad.
• Looking for the Action pop-up on a PDF you received. It works in messages you are composing.

Older workarounds from Apple Community threads

Some Apple Community threads describe older behavior. One poster said forwarding a marked-up PDF back to themselves worked before Ventura, but stopped working in Ventura. Another workaround from the same thread is to open the PDF from the Print window, choose Preview from the PDF menu, mark it up there, and attach the file again.

These threads are old and not official. Treat them as a last resort, and try the Action pop-up first. Apple's guide is the source to trust for current Mac behavior.

Does this work in iCloud.com Mail in a browser?

I could not confirm this. Apple's guide covers Mail on the Mac, and I found no Apple source that says whether iCloud.com Mail on the web supports PDF Markup. Test it with a sample PDF before you depend on it.

Apple does say Mail Drop works in iCloud.com Mail on a Mac or PC. That confirms the large-file route, not the Markup tools.

Next steps after you send

Once the message is ready, you may want to hold it for a set time. The scheduling guide shows how to send a message later.

If you sign off the same way every time, the signature guide covers creating a signature. For a file that keeps coming back, the Apple Mail app page lists the kinds of questions you can ask while you work.