Today, Apple releases its latest version of the OS X operating system for Macs, called Mountain Lion. It’s packed full of new features, as well as a layer of polishing, but it’s largely continuing the work that was begun with last year’s Lion.

In a nutshell

OS X 10.8 is a generous helping of iOS-friendly syncing apps and services, with a sidebar of unfortunately poor Messages and a grab bag of ‘most wanted’ features and tweaks to Lion.

It’s absolutely worth the $20 price tag to upgrade, as there is more good here than bad, and that’s super cheap.

Quick Links: Installing Mountain Lion - iCloud - Messages - Mail - Notification Center - Security and Gatekeeper - Safari - Sharing, Twitter and Facebook integration - Dictation - Calendar, Contacts, Notes, Reminders and Preview - System Preferences - The Mac App Store – Game Center - Finder and full screen apps - AirPlay Mirroring - Conclusion

Welcome to Mountain Lion

Many of Lion’s new features were designed to unify Apple’s OS offerings between its desktop and laptop computers, and its massively popular iPhone, iPad and iPod touch mobile offerings. Contrary to popular opinion, Apple isn’t in the process of transforming OS X into the mobile-friendly iOS. There’s simply nothing to be gained there and most of the underlying structure of iOS came from OS X in the first place.

What it is doing is attempting to unify the two halves of this whole, bringing some of the most-used features of iOS devices to OS X. This allows for a friendly and welcoming experience on the Mac for users whose first experience with anything Apple was an iPhone or an iPad. And those users are legion at this point. With some 350M iOS devices already on the market, and millions being sold each quarter, Apple’s primary business is now mobile computing. Everything it does to the Mac now and in the future, it will be doing to support that business.

Apple sees a future where the majority of people do their computing on mobile platforms first, and it’s preparing for that.

Mountain Lion is designed to take advantage of the significant halo effect of the iPhone, iPad and whatever other iOS devices the company introduces this year. Future versions of OS X will continue to take on the trappings of the mobile platform in order to make people feel comfortable and in order to make the two very different platforms feel like a cohesive whole.

This is why features like Reminders, Notes, Messages and Notification Center, among others, are appearing on Mountain Lion. These small pocketable computers have opened up a whole new swath of people to Apple’s way of doing things and these users are going to want to see familiar faces should they decide that their iPhone is so nice that they’d like to buy a Mac as well.

So, Mountain Lion continues the unification of Apple’s platforms by adding even more features found on iOS to OS X. But it also contains a healthy sprinkling of small improvements and polishing notes that feel very reminiscent of its Snow Leopard release. That was an OS designed to polish up the rough edges of Leopard, a major game-changing release that was big on ideas and a bit short on execution.

Mountain Lion is a significant release on many levels. It marks the first version of OS X to be released since Steve Jobs’ death late last year. It’s the culmination of Apple’s efforts to take advantage of the success of iOS in a big way. It also deeply integrates Apple’s data syncing service iCloud more fully than ever before, in an effort to make the experience of owning a Mac and an iOS device as painless as possible. And, on top of it all, it’s got to be faster and smoother than those that have come before it, or else.

Does it pull any, or all, of these goals off? We took a deep look at all of Mountain Lion’s major new features and many of its smaller changes in an effort to answer that question for you.

The new pattern of OS X updates

As you make your way through Mountain Lion’s updates, you’ll see a repeating theme. If an application got a major overhaul in Lion, it’s not getting much more than a polish here. The easy parallel to draw here is Mac OS X Snow Leopard, a release that was almost wholly devoted to polishing the rough edges off of OS X Leopard.

Leopard had been pushed back significantly in its development cycle, ostensibly to compensate for Apple having moved most of its resources into getting the iPhone ready to ship. As a followup to the massive shift in architecture implemented by OS X Tiger in 2005, Leopard introduced what Apple said were ’300 new features’. Some of these tightly coincided with the iPhone, like Core Animation, which is used extensively in the development of apps for iOS. This new core framework is directly responsible for how smooth the animations are in many of your favorite apps, and was a major reason the apps on the original iPhone looked and moved so well.

Others were more consumer oriented, like the easy backup service Time Machine and the virtual desktop utility Spaces. Spaces has since been absorbed into Mission Control, but Time Machine has stood the test of time, becoming one of the best things about owning a computer that runs OS X.

Unfortunately, the additions in Leopard weren’t all implemented as smoothly as they could have been. There was a lot of stuffing showing between the stitching and Apple knew it had to get its act together. Snow Leopard, the first version of OS X to be a variant on the name of the version before it, was announced as a maintenance release of sorts that would focus on improvements for developers, rather than broad user-based features.

Apple was entering into a period of its development where it brought all of the technologies that it had been developing for use in the iPhone and, later the iPad, up to a high level of usability for developers on the Mac. Less time passed between the release of Leopard and Snow Leopard than had between Tiger and Leopard, but Apple certainly wasn’t back on its ‘once a year’ track for OS releases.

In fact, the release of Mountain Lion this year marks the first time that Apple has released a year-over-year new version of OS X since 10.3 Panther. Coming in at the end of July means that it has been just about a year between the release of OS X 10.7 Lion and 10.8 Mountain Lion.

Apple is making a statement that it is aggressively pushing the platform forward, massaging the unifying glue of iCloud deeper into the OS and leveraging the power of a unified, seamlessly synced ecosystem. As the biggest company on earth, Apple can no longer afford to dawdle along with OS releases that leapfrog features every couple of years. Now, any major improvements in the core of OS X or iOS will be implemented simultaneously. If there is a release of iOS, there too will be a release of OS X.

This is why OS X 10.8 Mountain Lion is a sort of hybrid release. Many core features like Mail and the Finder got major updates last year, and they only get polishing this year. But many features introduced in iOS 5, like the iCloud-syncing Notes app and the location-aware Reminders app, make new appearances on OS X.

This is the new pattern for releases of OS X. A combination of major feature updates and refinements that are heavily informed by the advancements made in iOS.

Installing Mountain Lion

We’re now a year into Apple’s digital-only distribution of OS X, and it already feels completely natural. Call me optimistic, but the way that OS X Mountain Lion installs is the way that I always thought it should work. Simple, effective and painless, and all without physical media.

Last year, the concept was new, and ruffled some feathers from people who felt they should be able to get the application on a disk. Some because they felt that they should not have to have the Internet to install an OS and some that just didn’t have access to a reliable enough connection. But now, a year later, it just seems silly that it would work any other way.

I explained the difference between the edge cases, the hardcore customization geeks, and Apple’s main customer base last year:

But there’s going to be a far larger segment of people who will just install the thing and move on with their lives. They’ll do it because its logical, they’ll do it because it’s easy, and they’ll do it because it was inevitable. This is the segment of people that is the largest, the most willing to spend a few bucks for some cool new features and to ‘stay up to date’ and who are so busy that they would write an email thanking Apple for making the process so painless that they didn’t have to set aside a whole day to break down their machine, wipe the drives and install from scratch. Or they would if they had the time to write an email.

Just like Lion, OS X 10.8 creates a 650MB recovery partition on your drive and tucks away all of the files that it needs to boot your computer and reinstall itself directly over the Internet. This way any user can always get their Mac back to factory stock, sans disk, as long as their hard drive doesn’t go down. All you have to do to use this emergency partition is hold down the Option key while you boot up and you’ll be able to use it to diagnose issues, restore from a Time Machine backup and even reinstall Mountain Lion.

If you’re having a tough time accepting that this is the way that things are going to be from now on, think about it this way. There are probably going to be thousands of people that see the OS X Mountain Lion update appear in the Mac App Store and install it without any thought, and they’ll probably be just fine, despite having missed my review.

When is the last time you ever heard of any OS installing like that? Never. That’s the power of the Mac App Store and a company like Apple that isn’t afraid to cut ties, regardless of the cost in the court of public opinion. The user experience is wonderful and it should be a template that other operating system installation procedures should be modeled after.


If you work with computers regularly or have been downloading and installing apps to iPhones and iPads, then you’ve known for some time that the future of content delivery is digital-only. It’s an inevitability that has been slowed only by the size and ubiquity of the pipes that deliver our content to us. But now that broadband penetration is reaching the point of saturation, its possible to get pretty much any movies, music or software we want without buying a physical product.

That’s why Apple’s decision to make the delivery of OS X Lion available only by download from the Mac App Store shouldn’t have come as too much of a shock. Apple serves up millions of gigabytes of data a year to iPhones, iPads, and now Macs, already, why wouldn’t it step up to the next level and find a way to deliver its next OS as a digital download?

OS X 10.8 Mountain Lion follows suit in this, and can only be purchased from Apple’s digital store as a $19.99 download. This makes an upgrade installation almost completely painless, but it does make a ‘clean’ install a bit more tricky.

Compatibility and preparation

Unlike its predecessor, OS X Mountain Lion has a relatively complex compatibility matrix. There are many models that won’t run it at all and they aren’t all easily identifiable by processor, as with 10.7. The system requirements themselves are fairly straightforward: OS X 10.6.8 with 2GB or more of memory and 8GB of hard drive space. But the  64-bit boot EFI and graphics requirements of Mountain Lion mean that many older Macs are out of luck.

Here’s the official list of supported machines from Apple:

iMac (Mid 2007 or newer)

MacBook (Late 2008 Aluminum, Early 2009 or newer)

MacBook Pro (Mid/Late 2007 or newer)

MacBook Air (Late 2008 or newer)

Mac mini (Early 2009 or newer)

Mac Pro (Early 2008 or newer)

Xserve (Early 2009)

To figure out whether you have one of these machines, click on the Apple in the upper-left corner of your menu bar and choose About This Mac, then click on the More Info… button. If you’re running Lion, you’ll get a nice display that summarizes your machine’s specs and gives you the colloquial ‘model name’ term you’ll need to compare to the list above.

In addition to the model name, you’ll see the amount of RAM that your Mac has installed. This needs to be at least 2GB to install and run OS X Mountain Lion, although 4GB is recommended to run it properly.

Aside from a minimum model year, your Mac needs to be running at least Mac OS X Snow Leopard 10.6.8 or newer. Any version of Lion 10.7 and up will work fine as well.

Stop reading and back up your Mac

If you’re in the process of getting ready to install OS X Mountain Lion and you’re reading this article to get an opinion on it, then stop reading this and start backing up your Mac. You can let it back up while you read the rest. If you have backed up your Mac then you can continue.

I cannot stress enough how important it is to regularly back up your Mac. At least with the Time Machine backup utility that comes pre-installed on every Mac, or better yet with a hard drive cloning utility like Super Duper. If you have a hard drive backed up with Super Duper, you can be back up and running on your Mac within minutes, rather than the hours it might take to restore backed up data from a Time Machine archive. Not only is it completely free to use the cloning features of Super Duper, it’s incredibly simple to set up and use. I highly recommend checking it out. Better yet, use it alongside Time Machine to get the best of both worlds, quick access to your files and a complete clone of your hard drive for catastrophic failures.

Once you’re comfortable that you have a complete copy of all of the data that is important to you outside of the Mac that you’re installing OS X 10.8 Mountain Lion to, then please move on with the process of installing, but not before.

Preventative maintenance

These steps are simple preventative measures that you should take before upgrading any operating system installation. Although I found the upgrade of OS X 10.7 Lion to Mac OS X 10.8 Mountain Lion to be a simple, clean procedure on a relatively new Mac, there are dozens of variables that could mean trouble on your machine. A couple of things can help to prevent this.

First, turn off any encryption software that you have protecting all or part of your hard drive. This includes the built-in File Vault utility that comes pre-installed in Mac OS X Snow Leopard. OS X Mountain Lion uses a new version of the utility called File Vault 2 that works significantly differently, so it would behoove you to turn it off and back on once you’ve made the switch. Even though Lion uses FV2, I’d still recommend disabling it.

Next, you should launch the Disk Utility application installed on your Mac, select the drive that you’ll be installing OS X Lion to and select the First Aid tab. Click on Verify and wait for the results. If you find any errors, use your Mac OS X Snow Leopard install disk to repair the problems by dropping it into your CD drive, holding down the Option key while you restart and using Disk Utility from the Utilities menu to perform the First Aid operation. If you’re using a MacBook Air, use your provided install USB drive in the same manner.

Application compatibility

The biggest hurdle for upgraders is probably going to be application incompatibility with OS X Mountain Lion. There are three types of apps that you’re going to need to investigate before you make the switch. Applications that you’ve installed from the Mac App Store, applications that you’ve downloaded recently and legacy apps that you’ve been using for a very long time that just aren’t going to make the jump.

If you’ve purchased an app from the Mac App Store, then you’ll probably be okay to upgrade after opening the store and checking the Updates section to make sure all of your apps are up to date. Apple has sent out an invitation to developers to submit OS X Mountain Lion compatible versions of their apps, so they should be showing up soon if they’re not there already. If you purchased your apps outside of the Mac App Store, from a developer’s website for instance, or on a CD, then you should check each app’s software update option to see if there are compatibility updates available for it. Unfortunately, Software Update redirects to the Mac App Store in Mountain Lion, which means that you can no longer use it to check for third-party app updates en masse.

If you need to do a manual check on your apps to see if they are already compatible with OS X 10.8 or they have been updated previously, use the excellent Roaring Apps Wiki to search for all of your critical, most-used apps to ensure that they work. If they don’t, check the app’s website to see if the developers are going to update it for OS X Mountain Lion or have an update on the way.

The last type of app is the kind that OS X Mountain Lion will never support, the kind that still uses the older Rosetta translation software to allow applications written for the older PowerPC architecture to run on the new Intel-powered Macs. Apple announced that it would no longer support Rosetta with the release of OS X Lion. This means that any applications that you’ve been holding onto that depend on Rosetta are now officially dead unless they are re-written for the Intel platform. If you’re running Lion, you know this already because your Rosetta apps don’t work, but if you’re on OS X 10.6 Snow Leopard, then it’s something to note.

To find out which of your apps fall into this category, launch System Profiler, located in you Applications/Utilities folder, scroll downwards and click on the Applications section. Then sort them by kind and seek out the ones that say ‘PowerPC’ in that column. These are the apps that will never work under OS X Lion. Try to find replacements for these or see if the developers have newer versions designed to work without the help of Rosetta.

Basic upgrade procedure

With OS X Mountain Lion, the process of downloading and installing something as major as an operating system has been refined to an art. After you make your purchase in the Mac App Store, the icon for the Launchpad on your dock displays a download progress bar.

Once your download is complete your default course of action is simply to launch it from the Launchpad or the Mac App Store. You will be presented with confirmation page, a license agreement and a choice of install destination. Once those three pages have been navigated, your installation will begin.

In my experience, the process can take as little as 15 minutes on a Macbook with a Solid State Drive installed, or as much as 45 minutes on a computer with a traditional 5400 RPM drive. Apple’s onscreen estimates almost always state around 30-33 minutes at the start regardless. My 2011 i7 MacBook Air took around 22 minutes to finish installation and reboot. All in all, one of the quickest and easiest operating system upgrades I have ever done.

Doing a clean install of Mountain Lion from a bootable USB drive or DVD

If you absolutely can’t stand the idea of installing directly from an application on the dock, or you would like the safety net of a bootable USB thumb-drive that you can use to install OS X Lion on any computer, the process is mercifully simple. Just follow this procedure to make yourself an installation-ready USB drive or DVD.

To create a bootable DVD:

You will need to locate the OS X Lion installation package on your Mac. This will be located in your ~/Applications folder on your main hard drive after downloading it from the Mac App Store.

Once you’ve located the package, Option + click it and choose Show Package Contents.

Open the folder titled ‘SharedSupport’ and find a file called ‘InstallESD.dmg’. This file contains everything you need to boot up a computer and install OS X Lion. Drag this file out to your desktop or another easy to find location.

At this point, if you just want to make a DVD, open up Disk Utility on your Mac, find the Mountain Lion disk image in the list on the left, Option + Click on it and click ‘Burn’. You’ll now have a bootable DVD you can use to install Mountain Lion.

To create a bootable USB drive:

First, prepare a USB thumb drive at least 8GB in size by opening up the Disk Utility application on your Mac, plugging it in and choosing to Partition it in a 1 Partition scheme. Note that this process will erase your thumb drive, so make sure you’ve backed it up.

Highlight the single partition and use the pull-down menu to select ‘GUID Partition Table’ as the type and click OK.

Name the USB drive anything that you would like, make sure that the Format option is set to ‘Mac OS X Extended (Journaled)’ and click the Apply button.

Now, click on your new partition and click on the Restore tab at the top right. In the Source section, click on Image and choose the ‘InstallESD.dmg’ file from step 3.

Make sure that the Destination field displays the name of your USB drive and click Restore. You will be prompted to enter the password for your Administrator account. Once you’ve done so the copying process will begin.

Once the process is complete, you can verify the bootable status of your drive by selecting it and clicking Info in Disk Utility. Bootable status should show ‘Yes’.

Now that you have a bootable USB drive (or DVD) that contains OS X Lion, you can boot from it by plugging it in to any Mac and holding down the Option key while its booting.

Once the screen appears that asks you which volume to boot from, choose the bootable OS X Lion drive. This will enable you to install OS X Lion on any compatible Mac without using the standard upgrade procedure. If you’re the kind of user who likes to perform a clean install instead of an upgrade, this is a great option for you.

In general, I like to perform a completely fresh installation of OS X every 4-5 years if I haven’t changed machines in that time. If you’re still running on an install of OS X that is older than 4 years or so, read this excellent answer by Ryan Block to the question of whether Macs stuffer from ‘rot’, a condition that affects the speed and performance of machines with years of built up digital ‘plaque’.

iCloud’s roots grow deeper in Mountain Lion

With Mountain Lion, Apple has begun to massage iCloud deeper into the tissue of its desktop OS. Since iOS 5 was grown right alongside the iCloud service, it’s not too surprising that its sinews seem to mesh better with the service than Lion does. In fact, there was very little about the way that iCloud was integrated into OS X 10.7 that could be considered deep. With OS X 10.8, iCloud is a first-class citizen and the narrative of just how important the service is to Apple’s future is getting more fully fleshed out.

With OS X 10.8, Apple has finally acknowledged that there is a basic file system behind iCloud, something that it has shied away from with iOS. Whether the plans were in place to offer users a more direct method of accessing iCloud documents, or the realization was had on the fly, the end result is the same: more control over files in a visual way. In all fairness, there is a lot about the paradigm of iOS that just doesn’t lend itself to a full-on file browser. iOS is built from the ground up to be a file-less system and grafting one on at this point is unlikely to happen.

OS X, on the other hand, bases its nature on at least casual handling of files through the Desktop or Finder. It is unlikely that any user of OS X has never manipulated a file by at least dragging and dropping it. Because OS X has this different use case, it only makes sense to tweak how much access it gives users to the file structure of iCloud.

That’s not to say that there aren’t some thematic similarities in how iCloud documents are handled in iOS 5 and Mountain Lion, though. They’re very similar in fact.

iCloud setup

Apple wants every one of the users of its products to have an account for iCloud. With iOS 5, users are prompted to either sign into an existing account or create a new one on the setup of a new device. Mountain Lion brings this to iOS with a couple of additional steps added to the new Mac setup wizard. First among these is a screen dedicated to enabling location services on your Mac. These services are enabled on Macs with WiFi radios, and they’re available for use by a variety of apps. Chief among these, though, is the iCloud service Find My Mac, which allows you to track down your Mac if it’s lost or stolen, lock it and even wipe its data if recovery is not in sight.

The screen allows you to get more information about the services and choose to enable them. With its bevy of location sensing abilities, the iPhone is a natural place to utilize these kinds of services, but the kind of location-aware sensibility promoted by apps like Foursqare and Apple’s own services on the iPhone has been making its way to the Mac and apps on the Mac App Store, so it makes sense to create an easily accessible location toggle, as well as a permissions pane, which we’ll touch on in the System Preferences section of this review.

From there, you’ll be taken to the Apple ID pane, which allows you to enter your information to prime the iTunes Store and Mac App Store for purchasing. It also logs you in to iCloud and provides that login information to any app that uses iCloud integration, including all of Apple’s new OS X apps in Mountain Lion. Even after you’ve entered your information, though, you’re still offered the ability to choose whether to enable iCloud on your computer, with a splash screen featuring the trifecta of Apple’s iCloud ecosystem: the iPhone, iPad and Mac.

iCloud login gets you up and running on the following stock Apple apps and services right out of the gate:






Game Center



iTunes (Match, Stores)

Mac App Store


It will also now sync any user accounts you have set up for services like Twitter and email. This means that if you have a mail account set up on your iPhone, Mountain Lion will pull down the authentication information automatically.

If you’re upgrading from Lion, you won’t see these screens, but it’s likely you already have an iCloud account in place. If not, there is the dedicated iCloud control panel, which essentially identical to the pane in 10.7.

This login will be used to push your accounts and settings and other personal content from iCloud to your Mac. Any content you’ve shared to iCloud from an iOS device like contacts, documents and other items will also be used to fill out your Mac’s personal data.

This in-your-face onboarding of users to iCloud mimics the methods used in iOS 5. But there’s more than just a fresh new attempt to get users to get on iCloud right away, the service grows significantly in a major way by giving users access to the iCloud Document Library.

iCloud Document Library

In OS X Lion, iCloud was little more than a glorified syncing service. It made sure that accounts, contacts, calendar information and bookmarks were kept identical between devices, and synced photographs through Photo Stream. Find My Mac was probably the most impressive use of the service, allowing two-way communication and a general feeling that all was not lost if your Mac went missing.

Still, there were several big pieces to the iCloud puzzle missing, and one of the big ones has been added to OS X Mountain Lion: the iCloud Document Library.

The Document Library, lets call it the DL, is really a sidecar that exists in no central place but as a silo within each app that has it enabled. This silo allows apps access to documents that are relevant to it, but not a general pool of all iCloud documents.

The iCloud Document Library, then, is not a single repository that shows you all of your iCloud documents. Instead, it’s a section of each app’s document browser that is dedicated to iCloud. Using TextEdit as an example, if you hit the File>Open command, you’re presented with a normal file browser, with one addition. You can now choose to view the files ‘On My Mac’ or in iCloud. Clicking on either button will show you files in that location only.

The iCloud button is obviously the new one here and it takes you to a browser that displays files in a list or icon view. You can also create folders out of these documents much in the way that you do with iOS icons, simply by dragging and dropping them onto one another. You can then rename the folder by clicking on its name.

These files are limited to those that the current app you’re using has created or saved into iCloud, there is no cross-app access to iCloud docs here. This essentially means that each one of the iCloud enabled apps on Mountain Lion has its own slice of cloud storage. Since you can only see the silo dedicated to each app within that app, you’ll never see files that were saved to iCloud with other apps besides the one you’re using.

This behavior is very similar to the way that iOS handles file browsing, but with the added ability to access the local file structure. This makes the iCloud Document Library for each app a sort of grafted-on save location that allows you to sync those documents across your iOS devices and Macs.

When you create a new document in Numbers on your iOS device, for instance, you’ll eventually see the document in Numbers on your Mac, once the iWork suite has been updated to take advantage of the new Mountain Lion features, that is.

Your iOS device can only save to iCloud, period. On a Mac running OS X 10.8, you have the choice of saving it in iCloud and having it available to all of your apps through syncing, or saving it to your local file system only.

iCloud’s potential for confusion

This system brings up a massively confusing situation, however, when you realize that you can drag and drop any document into the iCloud Document Library of any app. That means, for instance, that you can open TextEdit, open the file browser and drop an image and a Numbers document into it from the Finder or desktop. So, you’ve got a silo meant for just text files, and you’ve added a document in an unknown format to that slice of iCloud.

When you add the document, it’s synced to iCloud, but it’s not available to any other applications. But, if you try to open it with TextEdit, it errors out, because the file is unknown to it. Frankly, it’s enormously confusing. With a per-app iCloud Document Library, Apple has effectively created a bunch of online boxes that people can use to store anything that they want. There’s an iCloud for TextEdit, an iCloud for Preview, so on and so forth.

Lets say I have a Numbers document on my Mac and I want to sync it to iCloud so I can open it on my iOS device. The proper procedure would be to open Numbers and drag that file into the iCloud Document Library inside that app. Even though it wasn’t opened and saved there, it should sync and be available everywhere. This is great, everything works just fine with this method and many folks should probably be fine with this.

But what happens when someone opens Preview, for instance, and sees the notice that they can ‘move their existing documents to iCloud by dragging them here from the Finder or other apps’? What if they drag a folder with a dozen Numbers documents into TextEdit’s iCloud Document Library? I’ll tell you what happens. The files are synced via iCloud, but completely inaccessible by any other copies of Numbers because they’re in the TextEdit iCloud Document Library, which is its own silo. And TextEdit can’t open them because it doesn’t understand the document format.

It’s like adding dozens of Dropboxes to OS X, each of which is only accessible by a specific app.

Now, I get that the iCloud file system was designed to streamline the access procedure for documents, in order to let people open an app and just work on the documents intended for the app. That makes some sort of sense, especially in light of the fact that whatever system that they had to come up with, it had to work across OS X and iOS in a very similar way. But allowing users to simply drag documents into these windows is incredibly ill-advised, and could lead to a lot of confusion as people store files in random hidey-holes that they have no access to on another machine.

Simply preventing users from dragging files into these boxes that cannot be opened by the app that controls the box would fix the problem. This is the way it should work now. Drag a Numbers app onto the TextEdit iCloud Document Library and get a message that this file is not compatible with this app, and that the user should place it in the iCloud Document Library of Numbers or another compatible app.

Note that nowhere on the system is there a central repository that allows you to view iCloud files of different types all in one place. This exacerbates the situation as you can’t see all of your various files in their own little silos at once. There are some indications that Apple is developing a web interface for this, but an iCloud Documents icon in the Finder’s sidebar that allows you to view all of the files in your personal iCloud storage at once would be hugely welcome.

Sharing out of iCloud Document Library

As with the system-wide sharing options, you can use the Share button in that it’s contextual to the type of file being shared. If it’s an image, you’ll see the standard Email, Message and AirDrop icons, along with picture sharing services like Twitter, Facebook and Flickr.

The same goes for video files, which get the Vimeo option. Other than this, sharing from the library is the same as it is anywhere else in OS X.

Messages: The worst shipping component of an OS X release in recent memory.

When Apple announced its iMessage service alongside iOS 5 last year, the implications were immediately evident. It was taking on the carriers monopoly over text messages and it would lead to seamless communication between iPhone users as well as those using iPads and iPod touches. Since then, iMessage has been massively successful, with a potential market of some 240 million iOS users capable of running iOS 5 and currently still using those devices.

Meanwhile, the text message bills of iPhone users continue to fall as iMessage usage rises.

When Lion was introduced and it was revealed that it incorporated many of the features we’d come to expect on iOS, it was inevitable that Apple’s desktop computers would eventually gain support for iMessage as well. And now, with Mountain Lion, they have.

Messages is essentially iChat with iMessages grafted onto it. And I don’t say that lightly. The undercarriage of Messages is, in fact, iChat. There is very little about the structure of the app that has been changed. The package that launches Messages even still contains references to iChat in various assets. If you thought of Messages as a re-skin of iChat with iMessage grafted on, you’d be on the right track.

All of the services you could use on iChat are still here on Messages. This includes AIM, Jabber (Google Talk) and Yahoo. All of the things that you could do before, including screen sharing, audio and video calls and threaded text conversations, are still present. The settings panel for an AIM account has video relay chats set to off by default, so if you want to use it as a video conversation conduit to an AIM buddy, you’ll need to turn those on.

But the marquee addition here is, of course, support for iMessage. It’s become so second nature for me to have iMessage at my fingertips that when my phone lights up with a notification, I glance at the Messages icon or window to see who is texting me. If it’s not there, I get irritated, because I know I’ll have to pick up my phone and use it to text the non-iMessage user back using the phone’s keyboard instead of dashing off a reply and getting back to work. It’s so insanely convenient.

Early on, the beta versions of Messages had a severe alert problem, and some of that still exists. If you’re messaged via one of the other types of accounts, only Messages will alert you, of course. But if you get an iMessage, all of your devices will get an alert unless you have the Messages window focused, then only Messages will get an alert, though your message will appear in all threads on your iDevices and the Mac.

There have been some improvements though. For instance, if you get a message and an alert appears in Mountain Lion as well as on your phone, it will get cleared off of your device if you focus the Messages conversation or click on the alert window. The same goes if you swipe-to-reply the notification on your device, which clears the ‘new message’ indicator in Messages.

Except when that doesn’t work. Which is sometimes. Maybe it will work immediately, perhaps there’s a delay. Sometimes it’s only on the next reciept of a message that it clears. Apple is obviously using it’s push notification system to trigger these alerts and to trigger when they go away, but it’s still all a bit shaky as to when the signals are sent or acted on by devices.

To start a new conversation, you click on the new button and then start typing a contact’s name. If they’re in your buddy list or in your contacts with an iMessage number, they’ll show up in a list. You can also initiate conversations with registered iMessage email addresses, allowing you to talk to iPads and iPod touches that have Messages installed. Sending messages to more than one person is as easy as typing more than one contact into the field at the top. Next to each entry will be an indicator of the protocol you’ll be using to talk to them. The protocol is also displayed in the text entry box at the bottom, allowing you to see what kind of message you’re sending.

By default, Messages will show you a typing indicator, allowing you to see when others are writing you messages. If you’re talking to someone who is using iMessage, it will show you a delivered indicator, letting you know that the message got there. If the user has the option enabled, it will also show you when they’ve read the message by either opening their Messages app on iOS or focusing the Messages app on OS X Mountain Lion.

Messages in full screen is a waste, don’t bother. If you’re confused by the technicolor output of your chat bubbles when you first first fire up Messages, it’s because it seems to randomly assign colors to you and the other party. If you’d like to have a more uniform look, you can specify these colors in Messages’ preferences.

The buddy list that comes packed with Messages is essentially the iChat list, and still offers the video chat and screen sharing options for compatible services. Unfortunately, iMessage is not integrated into this list, and the numbers are pulled from your Contacts, rather than appearing here. This makes some sense as there is no real ‘status’ of an iMessage account. But it does make starting conversations via iMessage are a bit trickier.

You can send images and files of up to 100MB in size to AIM, iMessage and Google Talk users who have the options enabled, but you can’t share whole folders at a time, they must be archived into a package.

While file sharing is technically supported by Jabber and AIM, we found that it was nearly impossible to count on this being the case. At times, we were able to transfer files to users of those protocols, and other times we just got proxy errors or the sends just failed.

The only reliable file transfer service was iMessage, which almost never failed to send PDFs, images or sound clips, either to mobile devices or to users on their own copy of Messages.

Messages supports multiple conversations at a time, and they’re presented in the sidebar of the main window. Unfortunately, it doesn’t group conversations from multiple protocols together, each is presented separately. This means that you can have 3-4 conversations going with the same person if you talk to them on different services. It would be great to see these grouped together, so that you didn’t end up with one for AIM when they’re on a desktop and another for iMessage when they’re talking to you from your phone, etc. It clutters up your messages window quickly. It probably wouldn’t be easy to thread these together, but a small dropdown that allowed you to choose your protocol of choice in the text entry window could work.

The unified search bar works generally fine, and it does a good job of picking out words or phrases, but it would also be nice to search within a single conversation window.

Viewing conversation history is done well, as Messages begins loading previous messages as you hit the top of the most recent set. You can also enable an option in the preferences that lets you save a log on the close of a conversation, which would otherwise delete it completely.

The way that Messages handles Facetime calls is also awkward, because you can’t have them directly in the app. You can click the camera button in an iMessage conversation window and choose a contact number or email to use to initiate Facetime, but then you’re dropped out to the Facetime app. It’s awkard and makes for a clumsy experience even when compared to AIM or Google Talk.

Now, the really bad news. Throughout the testing period, and right on through to the final ‘golden master’ release of Mountain Lion, Messages has been incredibly buggy for us. The app spontaneously drops account connections continuously, including iMessage. This forces you to open the preferences pane to ‘disable/re-enable’ the accounts, or re-launch the app entirely.

The icon on the dock also gets stuck displaying the ‘messages waiting’ badge, even though there are no messages there. Every once in a while, when you open the app, it will vomit up weeks worth of conversations as new, cluttering your sidebar with false positive new messages and racking up the count on the icon in the dock. Thankfully, you can click on the dock icon to bring you to the next new conversation, this means you can rapidly click it to take you through all of the false ‘new’ entries. That’s not annoying at all.

Conversations often break when you’re sending messages from multiple devices other than your computer, leaving you with partial discussions on your Mac, with no way to tell where you left off. We experienced few outright crashes, but there was a lot of voluntary force quitting of the app due to problems. This is one of the worst components that I can remember shipping in an Apple OS in recent memory.

The saddest part of the whole Messages mess? I use it. A lot. I use it because iMessage support is so, so very convenient. But it’s the shining pair of golden wings supporting the putrified vestigial body of iChat.

A dedicated version of Messages that was just for the sending and recieving of iMessages might have been the better way to go here. Leave iChat alone, as a standalone multi-IM client, and have a Messages exist as its own beast. As of now, there is a lot of polishing yet to do to get Messages to match up with its potential.

Mail gets full iCloud syncing and a VIP list

Mail 5.0 was a major new release for Apple that brought the aesthetic of the iPad’s Mail.app over to OS X. It also began to incorporate some of the nicer elements of web-based email like threaded messages. By consolidating your email accounts into the universal OS X accounts pane, it also paved the way for Apple to expand iCloud as an ecosystem-wide single sign-on service.

In Mail 6.0, the changes are not nearly so expansive. The look and feel of Mail remains nearly identical, aside from a few tweaks like the removal of the ‘Show related messages’ button from the toolbar at the top. The option is still there, it’s just tucked away under the view menu now.

Mail also no longer handles the note syncing duties in 10.8, where those have been offloaded to the Notes app. So if you’re looking for your synced notes, they’ll be in the dedicated app. This includes notes from iCloud and those from other accounts like Gmail. This icon, as well, is missing from the top toolbar. Whether the removal of notes from Mail is a good thing or not will likely depend on your workflow. Some may find it a relief not to have to manage notes in an essentially unrelated app, but the Notes app doesn’t offer nearly as concise a ‘file menu’ for browsing notes as is present in the Mail sidebar. Either way, it will likely take some getting used to and I wouldn’t be surprised to see some confusion result when those who are used to seeing Notes appear in Mail are suddenly bereft of them on upgrade.

RSS is also completely gone from Mail, as it is from Safari, so if you used Mail 5.0 as your newsreader, you’ll have to find a third-party option that you like. I’m not sure what’s behind the move, but I’d wager to say that the number of users who relied on Mail as their sole RSS reader was likely very low. RSS as a whole is still very much around, but other information services like Twitter have taken its place for many younger users. And it’s not as if there isn’t a relatively robust ecosystem of decent RSS readers for the Mac like Reeder, NetNewsWire and Fever. So, yeah, if you’re a Mail + RSS aficionado, Mail 6.0 is bad news for you.

iCloud comes to town

For the first time in OS X, Mail now supports iCloud syncing in a big way. Not only does your account information get synchronized with any other Mountain Lion machines logged in to iCloud, you get a bunch of other cool tidbits pushed over as well.

The following information is now synced via iCloud:


Recent Senders



Flag Names

Smart Mailboxes

Mail Rules

Account Information

This is a big step forward for Mail, as it’s always one of the fussiest apps to set up on any new machine. The addition of the centrally located accounts pane in OS X 10.7 Lion was a nice improvement, but full iCloud push of preferences is a great way to keep any fiddling and tweaking you do consistent across all of your computers.

The addition of iCloud to Mail in such a big way coincides well with the full iCloud system sync support in 10.8 Mountain Lion. Being able to clean install and fire up a new machine with all of your preferences already set up via iCloud is a cool feature, and Mail is a big chunk of that goodness.

VIP treatment

One of the biggest additions to Mail this time around is the option to set certain contacts as VIPs. This allows you to view a mailbox explicitly for messages from close friends or important contacts. The VIP list is limited to 100 contacts, so this isn’t a mailing list utility, it’s used to create a ‘must read’ list of your favorite email senders.

To create a VIP, hover to the left of the name of a sender in any message header and click the star icon, or click the arrow that appears next to an email address and pick it from the drop down menu. Once you’ve added someone to your VIP list, a separate Smart Mailbox will appear in your sidebar that collects all of the messages from your VIPs. If the person already exists in your Contacts list and has a few separate email addresses associated their name, messages from any of those addresses will get added to VIP. To remove someone from the VIP list, click the arrow next to their name in any message header. If you use iCloud Contacts, these VIPs will be automatically added to Mail on your other Mountain Lion computers also logged into iCloud.

Adding a new VIP section has a couple of benefits. For one, it allows you to quickly surface personal or important messages without any complicated mail rules or wrangling of folders. For many people, just having a simple place to put emails from their kids or close friends will go a long way.

But it also works very well with the new Mail Notifications system that Apple has introduced with 10.8. This is a component of Notification Center, the system-wide collection of all the various notices thrown at you by apps. An app must choose to support the Notification Center, but once it does, it gets to display its notices on your desktop and place an entry into the NC itself. Mail is one of the apps that does this out of the box, and there’s a new section of its Preferences pane that is designed to let you choose which mail messages trigger a notification.

The default setting is ‘Inbox’, which means that you’re going to get a notification on your desktop, and an entry into Notification Center, for every new piece of email that you get. If you’d like to narrow that down, you can choose to only trigger notifications when you get an email from someone in your Contacts list. To winnow down even further, you can just use that handy list of VIPs that Mail 6.0 now lets you create. If you’d rather get notified for everything, no matter how it is filtered or sorted already, you can choose the All Mailboxes option.

The Mail notification will appear according to how you have it set up in the main Notifications control pane. Either a brief banner which disappears on its own, or one that must be viewed or dismissed by hand.

Adding VIPs also lets you set up Mail rules based on a tighter group of friends. If you set up your family as VIPs, for instance, you can now choose a ‘Send Notification’ action that ensures you see important messages from both your cross-boundary VIP list and your contact list.

Inline find comes from Safari to Mail

The ability to find terms or phrases on a webpage in a clever highlight view was added to Apple’s web browser way back in Safari 3, and has become a staple. With OS X 10.8, it finally comes to Mail, and it&

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