Mobile deathmatch: Windows Phone 7 vs. Apple iPhone 4

Microsoft has a very slick device, but it can’t do nearly as much as the iPhone — especially in business.

You know how in monster movies, the lumbering creature always manages to outrun the frantically running victim? That seems to be Microsoft‘s (NASDAQ: MSFT) hope in competing with Apple: Despite a late start and slow development, it will crush the iPhone out of sheer size. Microsoft’s creature of choice is Windows Phone 7, available on devices from Samsung, LG, and HTC.

In a twist on the monster metaphor, the competition is not between beauty and beast. Windows Phone 7 has a very elegant user interface that is nearly as beautiful and intuitive as what Apple produces. The competition is really between capabilities, of which the iPhone has many and Windows Phone 7 has fewer.

For example, Windows Phone 7 doesn’t support HTML5-based websites, the Adobe (Nasdaq: ADBE) Flash Player, device-wide search, multitasking, copy and paste, or on-device encryption. The iPhone 4 — specifically iOS 4.1 — supports all but Flash; the iPad supports all but Flash and multitasking, but will gain multitasking when iOS 4.2 ships this month.

Some shortcomings could be red lines for certain users. For example, on-device encryption is required by many companies to gain access to email and other servers, so many businesses might be unable to support Windows Phone 7 users. Others, such as the lack of Flash, haven’t hurt the iPhone and may not hurt Windows Phone 7. The iPhone also didn’t support copy and paste or multitasking for its first two years of existence, yet became a formidable presence in the mobile market anyhow.

But in this day and age of mature, aggressive mobile contenders such as Apple’s iOS and Google’s Android, it’s hard to believe Microsoft’s omission of these capabilities will be forgiven by most users.

Still, its attractive UI will appeal to many people, especially those resistant to drinking the Apple Kool-Aid. That elegance was quite pronounced on the Samsung Focus smartphone I used for testing Windows Phone 7; the Focus is a snappy performer, with a big, beautiful AMOLED (Active Matrix Organic Light Emitting Diode) screen, as well as very nice fit and finish, though its touchscreen didn’t always register my taps. It does not have a physical keyboard; look to the LG Quantum if you want such a feature.

Deathmatch: Email, calendars, and contacts

For testing, I used a personal IMAP account, a personal Gmail account, and a work Exchange 2007 account. Both devices work directly with IMAP and Gmail, as well as with POP, so my email, email folders, calendars, and contacts all flowed effortlessly among the smartphones, my laptop, and the server. The configuration was trivial, and both devices try to auto detect your settings wherever possible.

Setting up Exchange access on both devices was also simple. However, Windows Phone 7′s lack of support for on-device encryption meant that InfoWorld’s Exchange server wouldn’t let it connect, as one of our three Exchange ActiveSync (EAS) policies requires on-device encryption; thus, I can’t tell you how Windows Phone 7 works with Exchange email, calendars, or contacts, as I can’t access them. Given how basic a requirement on-device encryption is for enterprise security, Windows Phone 7 simply can’t be relied on in a business context. (And using Webmail is no fix; the Webmail screen is simply torturous to navigate in Windows Phone 7′s IE7 browser.

Basic email functions. Working with emails is easy on both devices. You can reply, forward, mark as unread, delete, and move messages while reading them. In Windows Phone 7, you need to tap the more (…) button to see some options; on the iPhone, some options are in the message body itself. On both systems, you can easily delete individual messages from the email list: Swipe to the left and tap Delete on the iPhone, or tap and hold the message header, then tap Delete in Windows Phone 7.

Both the iPhone and Windows Phone 7 let you search emails, but Windows Phone 7 isn’t as good at it. It searches only the current folder, whereas the iPhone searches all your email. The iPhone lets you refine your search or your email list’s display by From, To, and Subject fields (as well as All); Window Phone 7 does not.

Getting to the top of your email list isn’t so obvious in either. In the iPhone, tap the top of the screen. In Windows Phone 7, slide over to unread or urgent messages, then back to all. Neither has a quick-jump shortcut to go to the bottom of your list.

Email management: Windows Phone 7 displays emails in a simple list for each account you have; they appear as separate panels — app icons, essentially — on the home screen. But you can’t see all emails from multiple accounts in one view, as you can on an iPhone.

Navigating emails is easy on both Windows Phone 7 and the iPhone, and Windows Phone 7 has copied the iPhone’s approach to moving and deleting messages in the list: Tap Edit, select the messages, then tap Delete or Move. Windows Phone 7 has a neat capability unmatched in the iPhone in which you slide your email list to the side to see just unread messages; slide it again to see urgent messages; and one more time to return to all messages.

Windows Phone 7 adds an unnecessary step when you want to view your email folders. When you tap the Folders button, you get a screen with two options: Inbox and Show All Folders. (If you’re in a folder, you also get the current folder name in the list.) You have to click twice to see your folders. The iPhone lets you tap an email account to go straight to its folder list, though you have to use the second accounts list in its Mail app; the first list brings you to just their inboxes. Both operating systems could do better in terms of folder access.

Windows Phone 7 does not automatically sync mail folders with the server when you open them, as the Phone does. And the iPhone lets you set in its preferences which folders you want autosynced; Windows Phone 7 can’t do that.

The iPhone 4 has a message threading capability, which organizes your emails based on subject; you click an icon to the left of a message header to see the related messages. That adds more clicking to go through messages, but it also removes the effort of finding the messages in the first place. (iOS 4 lets you disable threading if you don’t like it.) Windows Phone 7 has no equivalent.

I was annoyed that Windows Phone 7 doesn’t support PDF files out of the box; you have to download the Adobe Reader app from the Windows Phone Marketplace. It does open images and Office files, though, after a two-step process of downloading the attachment, then opening it (tap and hold each time). The iPhone’s built-in QuickLook viewer handles a nice range of formats, and it opens attachments with one tap, downloading them if needed at the same time. But the iPhone doesn’t open zip files, whereas Windows Phone 7 does.

Both the iPhone and Windows Phone 7 remember the email addresses of senders you reply to, adding them to a database of contacts that it looks up automatically as you tap characters into the To and Cc fields. Both devices let you add email addresses to your contacts list, either by tapping them (on the iPhone) or tapping and holding them (in Windows Phone 7).

Contacts and calendars: The iPhone 4′s more stylish UI for email applies to its Contacts and Calendar apps as well. Both the iPhone and Windows Phone 7 offer the same views: list, day, and month. The iPhone’s calendar is easier to navigate, with better indicators of days that have appointments in the month view; Windows Phone 7′s list view is too spare, so you lose differentiation among objects, and its month view makes it hard to see which days have appointments.

You can easily switch calendar views in the iPhone 4 in the main calendar screen; Windows Phone 7 also makes switching easy, both through swipes and through its button row at the bottom of the screen. Both can display multiple calendars simultaneously.

On the iPhone, your invitations for Exchange accounts show up in your calendar so that you can accept them with the full context of your other appointments. For other email accounts, you’re stuck; it doesn’t let you open the .ics invitation files in Mail, nor does Calendar detect them. As Windows Phone 7 won’t work with my corporate Exchange server, I can’t say how it handles Exchange calendar invites. For other accounts, Windows Phone 7 lets you accept invitations by tapping a menu in your message. You can even send a proposed alternative time and date.

Windows Phone 7 lets you issue invitations from its calendar; the iPhone does not. Note that Windows Phone 7 doesn’t send the invites immediately, so it’s not so good for planning an urgent meeting. But Windows Phone 7 has a nice feature: You can tap a button that composes an “I’m running late” email addressed to the meeting’s attendees.

Both the iPhone and Windows Phone 7 have capable Contacts apps, but the iPhone 4 makes it easier to navigate through your entries. You can jump to names by tapping a letter at the side of the screen, such as “t” to get to people whose last names begin with “t,” or seek quickly for someone in the Search field by typing in part of the name. In Windows Phone 7, you have only the search capability to find contacts; there’s no quick-jump function.

Windows Phone 7 lets you designate users as favorites, to put them in the Home screen. The iPhone 4 has no equivalent. And Windows Phone 7 lets you link contacts, so you can see all their information in one place, such as personal and business entries for the same person, or separate entries for family members. The iPhone supports email groups, but you can’t create them on the iPhone; they must be synced from your computer’s contacts application. Windows Phone 7 has no group list capability.

The winner: The iPhone, thanks to its support of critical Exchange ActiveSync policies. If you don’t use Exchange, the two mobile OSes are fairly equivalent. The iPhone is slightly better in its email handling, but Windows Phone 7 is better for calendars. Contacts management is a draw.

Deathmatch: Applications

The iPhone provides more useful apps than Windows Phone 7 does. Both provide email, contacts, calendar, browser, calculator (except on the iPad), maps, a music player, photo display, a video player, multi-user gaming, and SMS messaging apps. The apps are equivalent in most cases. One exception is the photos app, where the iPhone supports albums and Windows Phone 7 does not. Another exception is the maps app, where the iPhone provides satellite views in addition to cartographic ones; the iPhone’s maps app is also much faster at returning directions.

The iPhone provides several apps that Windows Phone 7 does not, including those for a clock, the weather (except on the iPad), stocks, voice memo, and YouTube. Although Windows Phone 7 supports alarms, it offers only a subset of what the iPhone’s clock app does.

Windows Phone 7 has a set of apps called Office: Word, Excel, and OneNote. But don’t let the Office name fool you — Word and OneNote are very rudimentary apps, good for basic notes entry and extremely light editing. For example, tap and hold a word to select it; from there, you can make it bold, apply a colored highlight to it, or add a note — but you can’t select a range of text. You can’t choose fonts either, though you can apply numbered and bulleted lists.

Excel likewise is good only for very basic editing; constructing formulas is very difficult, as you can’t tap a cell to enter it into a formula. You can tap the fx icon to get a list of formulas, as in the desktop version, but the default keyboard for Excel doesn’t display two of the most common symbols used in formulas: = and *; you have to switch to a second symbols keyboard.

Ironically, Windows Phone 7 lets you access SharePoint servers to open documents stored there — yet any organization that uses SharePoint is certain to require security policies for corporate access that Windows Phone 7 does not support. Document access via cloud services such as Box.net and Dropbox are not supported.

The iPhone comes with a basic note-taking app. It uses a hard-to-read font but is otherwise easy to work with for simple documents (no formatting allowed). If you want Office-like functionality, you’ll need to buy an app such as the $15 Quickoffice or $17 Documents to Go. Both are far superior to Windows Phone 7′s Office apps when working with Office documents, so keep your fingers crossed for Windows Phone 7 editions.

App stores and app installation. Windows Phone 7 is too new to have much in the way of third-party apps available in the Windows Phone Marketplace, and most of the current stock is basic or forgettable — I haven’t seen attractive apps yet. Apple’s App Store also suffers from having lots of junkware, which comes with the territory of 99-cent apps, and it took some time for really useful apps to become available.

As a store, the Windows Phone Marketplace is poorly designed. You can choose from a bunch of categories and search within a store, but there’s no way to sort through the long list of options. By contrast, Apple’s App Store lets you view and sort categories much more easily.

Installation of apps is similar: After selecting an app, you confirm your store account information and wait for the app to download and install.

Both Windows Phone Marketplace and App Store reside on the home screen and alert you to when updates are available.

App management. The iPhone has a simple app management process. For example, it’s easy to arrange your home screens to cluster applications both on your iPhone and on your desktop via iTunes; you can also put them in your own folders. Just tap and hold any app to invoke the “shaking apps” status, in which you can drag apps wherever you want or tap the X icon to delete them (press the Home button when done to exit that mode). You can also arrange and delete apps using iTunes on your desktop.

Windows Phone 7 lets you pin apps to the home screen, creating a tile for each app there. You can then rearrange tiles by dragging them to a desired location on the app screen or delete them by tapping the X icon. All apps are available in an alphabetical list if you slide to the right of the home screen. You can’t rearrange the list or create folders, though.

The iPhone has long let you add Web pages to home screens as if they were apps. That’s great for the many mobile Web pages such as iphone.infoworld.com that are essentially Web apps. Windows Phone 7 has a similar capability.

Both the iPhone and Windows Phone 7 let you manage apps on your desktop using their iTunes and Zune clients, respectively. Microsoft has a beta sync client for Macs that works reasonably well for transferring video, music, photos, and podcasts to the phone — but it doesn’t let you manage apps.

Multitasking. iOS 4 brought multitasking, in a limited way, to iPhones this summer, providing APIs that let apps enable multitasking for specific functions, as well as a mechanism to switch among and close running apps. iPhone apps must be enabled by the developer to use the limited set of multitasking capabilities iOS 4 provides.

Windows Phone 7 doesn’t support multitasking at all.

The winner: The iPhone, thanks to a selection of apps and strong app quality that far outshine what’s available for Windows Phone 7. Plus, the absence of multitasking is a serious omission in Windows Phone 7.

Deathmatch: Web and Internet

In the desktop world, Microsoft is behind everyone else in its support for HTML5. The same is true in mobile, where it alone does not support the common draft specifications for HTML5.

For regular HTML4 pages, Windows Phone 7′s IE7-based browser works well, displaying pages with good detail, and allowing panning and zooming with the same gestures that the iPhone has popularized. The Web viewing experience — both quality and rendering speed — of Windows Phone 7 is similar to that of the iPhone, though zooming is not as smooth.

On some mobile-formatted pages, such as iphone.infoworld.com, Windows Phone 7 had trouble displaying the contents, while on others (such as m.yahoo.com) it did not. The pages Windows Phone 7 had problems with render perfectly fine in iOS, BlackBerry OS, webOS, and Android.

Because Windows Phone 7 supports neither copy and paste nor multitasking, you cannot select text or graphics and copy them elsewhere, such as in emails. You can share the URLs of Web pages via email or SMS. The iPhone supports copy and paste, as well as URL sharing.

Both OSes lets you open multiple Web pages, but you can view just one at a time. Windows Phone 7 uses one field for searches and URL entries, whereas the iPhone has one field for each. I think both approaches work just fine.

The two OSes let you bookmark Web pages and add Web pages to your home screen (called “pinning” in Windows Phone 7), but only the iPhone lets you place them in bookmark folders. Bookmarks are one big list in Windows Phone 7.

Neither device supports Adobe Flash. Microsoft has suggested it will do so in the future. Apple of course has no plans to allow Flash support, given Apple’s dislike of the Adobe Flash technology.

In a misguided effort to promote other Microsoft products, Windows Phone 7 provides only the Bing search engine, whose results are not always great. The iPhone lets you choose among Google, Yahoo, and Bing. (Google has made a Google Search app available in the Windows Phone Marketplace.)

But a nice capability in Windows Phone 7 is its ability to report itself to websites as a desktop browser, for those times you don’t want the site’s mobile-optimized pages, through a simple settings control for Internet Explorer. I wish the iPhone could do that to avoid some of the horrible mobile sites out there.

I also like the voice-recognition capability in Bing. It’s pleasantly accurate in letting you search the Web via voice — even more accurate than Android’s similar feature. The iPhone can’t search via voice recognition.

The winner: The iPhone, thanks to its support of HTML5, broad search engine support, and ability to copy text and graphics.

Deathmatch: Location support Both the iPhone and Windows Phone 7 support GPS location, and both can triangulate location based on Wi-Fi signals. As noted earlier, the iPhone’s maps app is better than Windows Phone 7′s, though both are serviceable.

Although both the iPhone and Windows Phone 7 ask for permission to use your location information, Windows Phone 7 does not provide controllable settings for location use by the device or individual applications, as the iPhone does. (Windows Phone 7 does let you enable location detection to influence its search results, but that’s not about helping you manage your privacy, as the iPhone’s capability is.)

The winner: The iPhone, for its better maps app and its ability to control location privacy at a granular level.

Deathmatch: User interface

Even in its early preview versions, it was clear that Windows Phone 7 had an elegant, simple, and usefully different interface. In many ways, it’s even simpler than Apple’s iOS. It also borrows many UI techniques from the iPhone — its gestures, its home screen management, and its email management — and some UI techniques from Android, such as its menu buttons.

I found it easy to use Windows Phone 7 — about as easy as iOS, in fact, despite differences in their approach. Windows Phone 7, for example, makes you scroll vertically, whereas the iPhone scrolls horizontally. Windows Phone 7 uses “more” (the … icon) pages for less accessed tasks, whereas the iPhone finds a way to include them or doesn’t bother with them at all.

Sometimes, though, the Windows Phone 7 interface is too spare, as if designed by a Steve Jobs wanna-be. The result in some panes, such as the browser’s Favorites list and the calendar’s list view, with large readable text on long lists that are hard to navigate or parse. Other UI elements cry out for more differentiation. The panels on the home screen, for example, are so similar it’s hard to find what you want. They’re also bigger than need be, forcing more scrolling than necessary (yes, you can and should rearrange them).

However, the iPhone does more than Windows Phone 7, and Apple’s designers have excelled at building interface controls that are invisible until required or until called by a gesture. I haven’t yet encountered similar UI approaches in Windows Phone 7, which will need such nuance if it adds more capabilities over time.

Operational UI. Windows Phone 7 is good about not getting in your way as you use the device. As with the iPhone, Windows Phone 7′s onscreen keyboard disappears automatically when you click outside of a text field.

The iPhone does a slightly better job of providing visual feedback, though Windows Phone 7 does a good job here too. For example, when you tap and hold to insert the text cursor, the iPhone shows you a zoomed view of your selection area, whereas Windows Phone 7 merely places an icon above your selection point.

Both the iPhone and Windows Phone 7 let you double-tap the Shift key to get a caps lock. Both display accented characters and symbols in a pop-out menu when you tap and hold some keys. Windows Phone 7′s symbols keyboard includes a bullet character — a nice addition — but in doing so buries the asterisk (*) key. Once you find it, you’re OK, but it would’ve been better if Microsoft had stuck with the standard QWERTY symbol layouts and added the bullet to an unused location instead. Windows Phone 7 also has a whole keyboard of emoticons, a nod to social networking users.

Pinching, zooming, and scrolling, as well as autorotation as you turn the device, work equivalently on the two mobile OSes.

Windows Phone 7′s use of the hardware Back button to navigate within apps, though simple to grasp, causes usability issues. If you happen to press the Back button once too often — to return to a previous state after opening, say, a formatting pane — you leave the app completely and back up into a previously opened app or to the home screen. You can return to the app and pick up where you left off, but I found myself constantly backing up too far.

Both the iPhone and Windows Phone 7 let you use voice commands to place calls, but Windows Phone 7 also lets you manage your music player via voice.

Text selection and copying. Windows Phone 7′s dearth of capabilities becomes very evident in its handling of text. First, you can’t select text ranges. The most you can do is tap and hold a word to select it, then replace it with a suggested alternative word or apply formatting to it in the Office app that comes with Windows Phone 7.

Second, you can’t copy text or graphics within or across applications, so you can’t copy and paste text into the Search box, or copy information from an email and paste it into your contacts. The basic sharing of information a user today would expect is simply not supported. In effect, Windows Phone 7 is useless for working with text beyond very simple activities such as jotting a note or composing a brief email.

By contrast, the iPhone makes it simple to select, copy, and paste text within and across applications. Tap and hold to move the text cursor anywhere — fields, Web pages, messages, you name it. You even get a zoom view of the text that you can scroll through, so you never lose track of your cursor. To select text, tap it; selection bars appear, which you drag for your selection. Tap elsewhere in the text, and Copy and Paste buttons appear automatically. It’s that easy. The iPhone acts like a computer when it comes to text, which makes it incredibly versatile.

However, I do prefer Windows Phone 7′s approach to autocorrection. The iPhone automatically corrects anything it thinks is a typo, unless you explicitly block a suggestion. If you’re typing fast and not watching its suggestions, you can end up with some very strange text indeed. (And it always miscorrect the plural of “it” to be “it’s” rather than the correct “its.”) Windows Phone 7 takes the opposite approach: It shows suggestions for what you’re typing as you type it, so you can select one if you want. Otherwise, you get what you type. Windows Phone 7 also lets you wipe out the learned corrections it stores over time; the iPhone does not.

The winner: The iPhone, by a mile. Although Windows Phone 7′s usability is strong for the overall UI, it falls down completely in basic text operations, severely restricting what users can do across the device’s built-in functions and any apps they may choose to install.

Deathmatch: Security and management The painful irony of Windows Phone 7 is how poorly it provides security. It is not usable in most business environments because of fundamental omissions such as lack of on-device encryption. Additionally, Windows Phone 7 doesn’t support static IP addresses or VPNs — two common access control techniques.

Windows Phone 7 does support some management and security policies through the Exchange ActiveSync (EAS) protocol; if your company doesn’t require on-device encryption, it can do remote wiping and require passwords to be enabled, for example. And it supports SSL encryption of email traffic over the air.

Still, Windows Phone 7 is less securable and manageable than its Windows Mobile predecessor — a stunningly bad decision on Microsoft’s part. It’s also less securable than the iPhone, whose iOS (with version 4) has become the second most securable mobile OS after BlackBerry.

iOS 4 covers much of what most businesses need for security and management. It has remote wipe, certificate-based authentication, and an assortment of password controls (such as requiring a strong password or disabling access after so many failed attempts to log in) that are manageable through Microsoft Exchange, as well as through iOS 4-enabled management tools from companies such as Good Technology and MobileIron. Apple has its own utility to deploy these security profiles, but it doesn’t scale well beyond a few dozen users; large businesses will want to look at third-party mobile management tools as they become available. iOS 4 also supports several types of VPNs and SSL over-the-air email encryption.

The winner: The iPhone, by a mile. Windows Phone 7′s security capabilities are simply not business-class.

The overall winner is … No question that the iPhone is far superior to Windows Phone 7, Microsoft’s surprisingly well-executed UI notwithstanding. Although Windows Phone 7 offers competitive email, contacts, and calendar capabilities, it falls short in every other category. And that’s not counting the extra depth and sophistication of the iOS in niche areas, such as its multilingual support, parental controls (a surprising omission for an ostensibly consumer-friendly device), and ability to search nearly every corner of the device from one location.

If you’re looking for a phone for entirely personal use, Windows Phone 7 would be a good choice. But no business beyond a mom-and-pop shop could responsibly allow Windows Phone 7 into its network or rely on it for productivity beyond email and appointments.

Had Windows Phone 7 shipped four years ago, there might not be an iPhone today, as Windows Phone 7 is very similar in strengths and weaknesses to the original iPhone. Had both existed four years ago, Microsoft’s market strength would easily have sent Apple’s mobile platform into obscurity.

But in those four years, iOS has matured into a powerhouse, and other competitors have strengthened as well. Windows Phone 7 is behind the iPhone, BlackBerry, and even the security-challenged Android. It’s ahead of just webOS and perhaps Symbian. Although Microsoft has promised to fix most of Windows Phone 7′s major omissions sometime in 2011, that’s likely too late for users.