A major update to OS X generally means that many of the apps included with the operating system also get major updates--or at least the biggest updates they're likely to get until the next major operating-system release. In OS X Yosemite, due this fall, several major Apple apps have received upgrades both big and small. I've been using a pre-release version of Yosemite (on an Apple-supplied MacBook Pro) for the past month and have had a chance to spend a little time with Mail, Messages, and Calendar. Here's a look at what's new.

Mail gets markup and more

My love-hate relationship with Apple's Mail app is currently in a good place. I'm using it every day and it's been working fine for me. Still, I was reluctant to test an early version of Mail on Yosemite with my real mailboxes. As a result, I can't testify yet about any potential compatibility issues between Mail and either my personal Gmail inbox or my work's Office 365 mail. (I can, however, testify that my rarely-used me.com email address is a stupendous collector of spam.)

Aside from a few slight interface tweaks--the Show/Hide toggle that displays the mailbox list is now more properly labeled Mailboxes--Mail looks much the same as it did in Mavericks. But this is not to say that there aren't some major new feature additions.

A feature I really like is Mail Drop, which eliminates the problem of emailing large file attachments. As someone who produces more than a few podcasts, I run into the issue of not being able to attach large files to email messages (the server rejects them) all the time. For years there have been workarounds, largely involving uploading a file to a remote file-sharing service of some sort and pasting in a link.

In Yosemite, that entire procedure is baked in to Mail--and it's all stuff that happens behind the scenes. If you want to attach a large file to a message, just drag it in and send away. Mail will upload the file to a temporary holding bin on Apple's servers, where it will remain for 30 days. Then the attachment is replaced in your email message with a download link to the file. (If your recipient is using Yosemite, Mail will just download the large file automatically, as if it had been attached to the message.)

This is a quintessential Apple feature, eliminating a common headache without forcing the user to change their behavior at all. I don't mind using Dropbox (or back in the day, YouSendIt) to exchange files with friends, but it's a multi-step workaround--and this is as simple and direct as it gets.

Another interesting idea added to Mail this time around is a feature called Markup, which allows you to add simple annotations to images and PDFs from directly within a Mail window. Here's how it works: You click on a file and an icon appears in the top-left corner of the file's preview. Click it and select Markup, and the item zooms out, with a toolbar appearing directly above the item.

Markup is actually an example of the new Extensions technology that's debuting in both Yosemite and iOS 8, in which code from an entirely separate application can appear inside another app's window. In this case, Apple's written a Markup extension that lets you draw lines, shapes, text, and more on PDFs and images. You can stick your signature on PDFs without ever leaving Mail. It's a pretty clever idea.

Unfortunately, I'm not thrilled about the implementation. Marking up a file really does feel like you're using a different program entirely--but one without keyboard shortcuts or a menu bar. I kept pressing Command-Z in order to undo mistakes I made in Markup, and it did nothing. The Markup controls are pretty simple--they feel more like an iOS app than a part of Mail, to be honest--but they definitely did the job once I got the hang of them.

Extensions have the potential to dramatically reshape how we use Mac apps, but they will take some getting used to. Also, it's early days--it seems that Apple does not currently give third-party developers the level of access that the Markup extension has. Right now, developers are limited in the locations where they can deploy Extensions, and attachments in a Mail message isn't one of them. That's probably a good thing, because it feels like Apple is experimenting with features like Markup. It might be wise to let Apple's own developers realize the strengths and weaknesses of Extensions before opening it up to everyone else.


Messages, Apple's go-to app for iMessage and miscellaneous other chat services (that's clearly the order of priority), gets a bunch of new upgrades in Yosemite that serve to enhance your conversations, so long as everyone is using iMessage. (Those miscellaneous other chat services are still supported, it's just that support for them appears to have been frozen in amber for several updates. If you truly love IM like many of my friends do, you'd probably be better off using an app such as Adium for those services, and keep iChat focused on iMessage.)

The marquee feature in Messages on Yosemite is probably Soundbites, which adds a microphone button next to your chat window. Click it, and you'll be able to record a brief audio message and send it via iMessage. (This feature is probably more useful on iOS devices, where it will arrive as part of iOS 8.)

In my testing, Soundbites worked as promised, though the audio quality left a lot to be desired--messages sounded more like lousy telephone connections than what I've come to expect from computer audio. I'm also not thrilled with what a chat window looks like after of a series of audio messages: it's just bubbles of audio files going back and forth, entirely inscrutable. Maybe some of that fancy speech-recognition technology could be brought to bear on these messages, so they were searchable (and even glanceable) without having to play them back one by one?

But there's still a lot to be said for asynchronous audio conversations. One of the reasons I text my friends and family instead of phoning them is that most of the time, I don't need to interrupt what they're doing right that second in order to get an immediate response--it's just not that important. With this new feature, especially on iOS, it'll be easy for us to hear each other's voices without demanding immediate attention with a phone call.

Group iMessaging also gets a big boost in Messages. Group messages get a new Details button (though the button looks like hyperlinked text, iOS 7 style, rather than a standard Mac interface element) that brings up a raft of options. You and your interlocutors can share your locations using the Find My Friends infrastructure, and the Details view will draw a map showing where every participant is located. You can also kick off phone calls, individual chats, or FaceTime sessions directly from the Details window, and add or remove participants. And just to help you keep track of your conversations, you can give each of your group chats a distinct name, like "Dinner Plans."

Perhaps most importantly, the new Messages lets you control group conversations that you might want to bail out of--or just not be interrupted by. You can select Do Not Disturb to no longer receive notifications from an ongoing group conversation, or click the Leave Conversation link to drop out completely.


Apple's Calendar app hasn't undergone as many changes in Yosemite, but there are a few worth noting. When you create a new event, it attempts to learn from previous events you've created and tries to autocomplete your event with likely dates and even attendees--if you often create a "Lunch with Jim" event on Tuesdays at 12:30, and you type "Lunch," Calendar will suggest Lunch with Jim, at 12:30, with Jim invited.

The Day view has been overhauled. It's still a two-pane view, but instead of the (fairly redundant) two daily schedule panes found in Mavericks, it's a single schedule pane and an inspector pane that shows you all the details of a selected calendar event. If you create a new event in this view, the inspector pane is where you enter in all the calendar information. It beats the cramped space in the floating inspector palette.

There's also a new option to display an Overlay Calendar--if you also need to know today's date in the Islamic, Hebrew, or Chinese lunar calendars, Calendar can now display them alongside the Gregorian calendar system.

End of the tour

This marks the last article I'm writing about the Yosemite beta based on my Apple-supplied copy of the first Developer Preview, released at June's Worldwide Developers Conference. Since then Apple's OS X engineers have been hard at work, and developers have taken delivery of two updates to Yosemite, all a part of the road that leads to the final release this fall.