OS X Yosemite: Using Mail's Awesome New Markup Feature

Maybe you’ve heard that you can now mark up certain types of files right from Mail, without having to open them into Preview and annotate them as a separate step. Since I’m constantly sending out instructions for how to do stuff on the Mac, this has been invaluable for me, and I think you’ll like it too. 

So when you’re composing a message in Mail and you attach an image or a PDF, hovering over the file with your cursor will reveal a small drop-down arrow at the upper-right corner. Click that and choose “Markup,” and you’re on your way.

When the markup window appears, you’ll see a series of useful tools at the top that you can use to manipulate your attachment. 

From left to right, here’s what they are.

Sketch. This will let you draw on your file, with the added bonus that it’ll attempt to correct your shape if you create something approximating a circle, square, oval, or whatever.

Shapes. You can add a…well, a shape to your attachment with this if you want to call out something in particular. 

At the bottom of this tool’s menu there are also a couple of special options. 

The icon on the right will bring up a loupe; the icon on the left will let you highlight a portion of your attachment.

That’s my favorite. Makes me look like I actually know what I’m doing despite all evidence to the contrary.

Text. This inserts a box to type some text into your attachment.

Sign. If you’ve added a signature in Preview, it’ll appear here; if you haven’t, you can choose to create one. This is very handy for filling out forms right in Mail.

Shape style. This’ll let you define things like line width, shadow, and arrow appearance for shapes you create.

Border color. You want a green square instead of a blue one? You got it, bub.

Fill color. Now you want your green square to be filled with yellow? This email is starting to get weird.

Text style. Change the font, size, color, and alignment of text you insert.

Finally, you can crop your attachments within the markup window, too, but there isn’t an obvious tool for that. To do so, just hover over the edge of the file until you see the blue grabby-handles, and then click and drag one of them to crop.

And yes, “grabby-handles” is the proper term. I did not just make it up. 

Once the crop is a size you like, you can even move the cropped area around by hovering outside of it (your cursor will turn into a hand) and then dragging to move it.

When you’re satisfied with your work, click “Done” at the upper-right corner, and your annotated file is ready to go!

Here are a couple of additional things to keep in mind. First of all, you can mark up PDFs and certain types of image files (JPGs and TIFFs), but other file types (such as PNGs, Word documents, and so on) are off the table. If you don’t see the little markup drop-down mentioned above when you hover over the file, you’re out of luck.

Secondly, if this feature isn’t working at all for you, make sure that System Preferences> Extensions> Actions> Markup is toggled on.

Also, once you send the marked-up attachment, none of your changes are reversible, just so you know. Your recipient can add new revisions of his own, but he can’t take off any ugly green and yellow shapes you’ve added. 

How will you guys use this fancy new Yosemite feature? Sending technical instructions to computer-phobic Uncle Rodney? Adding text to photos? Signing PDFs? I’m interested in hearing your ideas!