Do More with Mail

Yosemite’s Mail looks much as it did before, with only subtle cosmetic changes to its fonts and icons. But don’t let this fool you: Mail includes two big new features that can save you a lot of hassle. Mail Drop lets you send large attachments without running into server limitations. Markup simplifies collaboration by making it possible to annotate images and PDFs without leaving Mail at all ①.

① Mail’s new Markup feature lets you add notes to PDFs and images without ever leaving the app.

Send Big Files

Trying to send a big attachment by email can feel like stuffing a package through a mail slot. Blithely send out a 103 MB archive full of images and your email server typically will stop it in its tracks. Big attachments usually get bounced because they surpass the attachment size limit of either your service provider or the recipient’s.

Note: To brush up on the fundamentals, see Apple’s Mac Basics page on Mail.

Gmail’s attachment limit, for instance, is 25 MB, although you can send attachments up to 15 GB using Google Drive instead (1 TB if you’re paying for a storage plan). Both Yahoo and Comcast have 25 MB limits, too.

To send a hefty video, image, or presentation file, most people turn to a cloud-based file-sharing service like Dropbox, Google Drive, DropSend, or Box. But with Yosemite’s Mail you can send attachments totaling up to 5 GB per message without worrying whether they’ll make it to their destination.

For starters, Mail now lets you know if you’re going to hit an account’s attachment size limit ②. If you try to send a big attachment anyway two different things can happen:

② Mail now warns you if you’re going to hit an email account’s attachment size limit and even tells you what that limit is.

If you send from a non-iCloud email account:

If you’re using another type of email account (like Gmail or Yahoo), Mail asks if you’d like to send the attachment via iCloud. If you click Use Mail Drop, the attachment is uploaded to Apple’s server. (Attachments don’t count against your iCloud storage limits.)

Recipients see a link, good for 30 days, at the end of your message ③.

③ If you send your attachment from a non-iCloud email account (or your recipients receive the email in anything other than Yosemite Mail), a link like this will appear at the end of your email message.

As soon as they click it, they’ll be sent to an iCloud page and the file will download automatically ④.

④ When they click the link, they’ll be taken to a Web page and the file will begin downloading automatically.

If you send from your iCloud email account:

If you send a big attachment with your iCloud email account (that includes icloud.com, me.com, and mac.com email addresses), the message with attachment will just send. Recipients using Yosemite Mail will see a regular file icon in the message as the file downloads automatically from Apple’s servers. Other recipients will receive a download link identical to the ones sent by non-iCloud email accounts.

Note: To learn more about setting up iCloud and about your free iCloud email account, see Take Control of iCloud.

Start Marking Up

If you collaborate with others, chances are you’ve needed to add notes or a signature to something you were working on together. Markup lets you annotate images and PDFs from within Mail.

Previously this required opening the file in Apple’s Preview or another app, annotating it, saving it, and then attaching it to an email message. Markup saves you multiple steps and offers a nice selection of annotation tools.

To use Markup, first drag and drop a PDF or image onto a new Mail message (or a reply) and then hover over the attachment’s preview to see and click the Action button and choose Markup. A Markup pane appears. What can you do next? Here are some examples.

Tip: Even if you see only an attachment’s icon in your email message, the Action button will often appear when you hover your pointer over it. If not, Control-click the icon and choose View In Place.

Store Your Written Signature

Sometime you need to add your written signature to a PDF—whether it’s a W2 or a school consent form. Markup makes it easy:

Click the Sign button in the toolbar.
If you want to sign with a trackpad, click the Trackpad button and then the Click Here to Begin button. Use your finger to draw your signature on your trackpad ⑤.

⑤ To add your signature to Mail, use your finger to draw it on a trackpad.

Or, to sign with your Mac’s built-in camera, click the Camera button. Sign your name in black ink on a white piece of paper and hold it up to your iSight camera. Your signature appears onscreen in reverse; line it up so it is level on the blue line. When it looks right, press any key. If you don’t like the way it looks, click Clear and try again.
Click Done.

Now if you click the Sign button, you’ll see your signature in the popover ⑥. You can store multiple signatures—say, your own, your spouse’s, and your nom du plume when writing spy novels.

⑥ Click the Sign button to add your signature to a PDF. Drag the signature into place and then use the blue handles to scale it.

Sign an Attached PDF

With a PDF in the Markup pane, click the Sign button in the toolbar and choose a signature. The signature appears on the PDF.

Click and hold the signature—your pointer turns into a hand—and then drag it into place. Drag the boundary bars to scale it properly.

Add Text Annotations

It’s a cinch to add text annotations—a gentle note, perhaps—to your attached PDFs or images. When you click the Text button in the Markup toolbar, the word text appears at the center of the Markup pane in red letters. Double-click and the text disappears. Don’t worry, just type.

Quick Annotation Tricks

Select it: Hover your pointer over an annotation element until the pointer turns into a hand. Click to select. If you succeed, blue handles appear.
Delete it: Select it, and then press Delete.
Move it: Select it, and then drag it into place.
Scale it: Select it, and then drag any of the blue handles around it. (When the annotation element is text, this changes the margins instead.)
Alter a shape: For instance, by making an arrow curve—click and drag its green handle.

Format a Text Annotation:

Change the size or style: Select the annotation, click the Text Style button in the toolbar, and then adjust the settings that appear ⑦.

⑦ To change the look of a block of text, first select it. (Blue handles appear to either side when you succeed.) Click the Text Style button in the toolbar to see formatting options.

Stick to one style: You can’t apply more than one style to a single block of text. Create separate blocks of text to get different effects.
Change the margins: Hover over an annotation until your pointer turns into a hand. Click to select. If you’re successful, blue dots (also known as handles) will appear to each side. Click and drag these to change the margins.

Outwit Annotation Frustration

Having trouble selecting something? It may be behind another annotation element. This is likely when you’ve added multiple elements, like a circle, some text, and an arrow.

Control-click the element to see a contextual menu with the option to Bring Forward, Bring to Front, Send Backward, or Send to Back.

If the Bring to Front option is dimmed, you don’t have the right element. Send whatever you have selected to the back and try again.

Add a Shape

Sometimes it’s helpful to call out a part of a PDF by drawing around it. Likewise, an arrow pointing at an image detail can clarify exactly what you’re talking about.

Click the Shapes button to see a popover with choices, including a line, arrow, square, circle, star, speech bubble, hexagon, or rounded rectangle ⑧

⑧ Click the Shapes button to see all your choices. You can change how a shape looks using the Border Color, Fill Color, or Shape Style buttons on the toolbar.

Click a shape and it appears in the middle of the Markup pane. Or, drag it off the popover and place it as you like.

Resize a Shape

To resize a shape, drag the blue handles. If you see a green handle, drag this to change the shape. For instance, if you place an arrow and then drag the green handle at its center, the arrow curves.

Customize Your Shapes

Change shapes’ properties by using buttons on the Markup toolbar. Click the Shape Style button to alter the shape’s line. Choose from seven thicknesses as well as a dotted line, charcoal line, and more.

Click the Border Color button and choose a new color from the color picker. By default, most of the shapes have no fill, but you can add a color by clicking the Fill Color button.

Tip: Need a closer look? Press Command–plus sign to zoom in on the PDF or image. Press Command–minus sign to zoom out.

Tip: Markup lets you crop an image, too. Move your pointer to the Markup pane’s edges and then drag the blue handles in. Everything shaded will be cropped.

Draw Shapes Freehand

If you want more freedom to make custom shapes and callouts, use the Sketch tool. With this selected, you can draw with your mouse, or on the trackpad with your finger, to create arrows, speech bubbles, lines, and more.

Markup autocorrects shapes based on what you’ve drawn. For instance, if you draw a lumpy circle, it will smooth it out. For a moment after the shape is autocorrected, a floating palette appears with your shape as one of two options. If you like your lumpy circle just how it is, choose it ⑨.

⑨ When you use the sketch tool to draw freehand, Markup does its best to autocorrect your shape. A palette appears briefly. If you prefer your lumpy speech bubble, choose it there.

Zoom In on a Detail

Markup also lets you zoom in on an area, which can be helpful when you want to point out a small detail. Click the Zoom button on the Shapes palette and then drag it into place. To increase or decrease the zoom, drag the green handle. Drag the blue handle to make the lens bigger or smaller ⑩.

⑩ Use the Zoom button (circled) to zoom in on part of an image or PDF.

Focus on One Thing

Draw focus to a part of an image (and only that part) by highlighting it. Click the Highlight button on the Shapes popover and then adjust the boundaries to focus on the important part ⑪.

⑪ Use the Highlight tool to draw focus to one part of an image.

Commit to Your Changes

When you’re finished annotating, click Done.

You can tinker with the annotations until you send your message. After that, they become part of the image or PDF and can’t be changed.

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