The iPhone has been out for quite some time now and even has a major update under its belt with the iPhone 3G and version 2.x of the iPhone software.  Upon the initial release of the iPhone, many in IT were skeptical of this device’s enterprise credibility due to its inability to easily and seamless synchronize with enterprise mail systems – most notably, Microsoft Exchange.  Sure, the original iPhone supported POP3 and IMAP, but these mail exchange protocols are often disabled in the enterprise due to security and information management concerns.  As such, a mobile email device must be able to support native – and common – communications mechanisms such as ActiveSync.  Obviously, BlackBerry devices also fit this need very well.

For quite some time, users of Windows Mobile-based devices have enjoyed the benefits of ActiveSync and have also had 3rd party integration options from which to choose, such as Good Messaging.  Users of messaging devices running other operating systems, including Palm OS, could also choose to use Good Messaging as an excellent way to provide a fully integrated mobile device/Exchange experience with full bidirectional synchronization provided for mail, contacts and calendar items.  Good supports both Exchange and Lotus Notes, making it an excellent choice for users of both enterprise platforms.  I’m going to focus the rest of this post on Exchange since I don’t know a lot about Lotus Notes.

As of November 20, 2008, Good Messaging indicated that their software would not be supported on the iPhone due to significant limitations in the iPhone SDK.  That fact alone will prevent iPhones from making their way into some organizations that have standardized on the Good platform.

With the iPhone 3G and version 2.0 of the iPhone software, Apple has licensed ActiveSync from Microsoft and implemented it on their platform.  However, the overall email and calendaring experience – the primary reason that many people move to a device like this – is far from complete and will prove to be wholly inadequate for hardcore mobile users that have become accustomed to a complete experience under Windows Mobile.  With frustrations related to the inability to invite participants to a meeting to incomplete folder management to no support for flagging and unflagging messages, the iPhone email/calendaring experience is still miles behind Windows Mobile.   These shortcomings are well documented and have been written about by others, so I won’t rehash it all here.

On the plus side, what does work well on the iPhone works beautifully.  HTML-based messages render absolutely spot-on and it’s easy to set up multiple accounts; for example, I sync both my Exchange mailbox as well as my personal email account (IMAP).

So, the question is this: Is the iPhone enterprise-ready?  It really depends.  If you need just a simple device on which you can read and reply to messages (and you can learn to live without a physical keyboard) and you simply want to be reminded of upcoming appointments, the iPhone is a fine device.  If you need the deeper integration features, sticking with Windows Mobile is your best bet until Apple properly implements some seriously lagging features.

Personally, even though I lament some of the missing features, including the ability to invite people to a meeting, I’ve switched to the iPhone.  I’ve used a number of Treos (and performed one horrendous experiment with the Tilt) – both Palm OS and Windows Mobile-based – and have used both ActiveSync and Good Messaging, and can say with complete sincerity that, if Apple wants this device to be a serious contender, they simply have to fix these issues.  However, the iPhone does bring with it a whole host of other features that, for me, make it a compelling choice.  I work from pretty much everywhere and don’t always have a laptop with me, but can more easily do some things – shop at Amazon, for example – that I would ever be able to do with a Windows Mobile-based device.  Further, although there are large-screen Windows Mobile devices, one can’t look at an iPhone and not be impressed with the screen size, clarity and responsiveness.

Until then, I keep my laptop a little closer than I used to, and keep my USB 3G adapter in my bag, just in case I need to do something from afar that I can’t do on my iPhone.

Oh, yeah – if anyone out there knows how to make the iPhone sync multiple folders rather than just the contents of the Inbox, leave a comment.  I make really heavy use of server-side rules for email management.  Under Windows Mobile, it’s possible to choose which folders to sync and they do so using Push.  So far, I haven’t figured out how to do that on the iPhone.

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