Outlook separation anxiety holds back Google Apps

User attachment to the Microsoft e-mail client forced Google to build an Outlook sync tool for Apps

In its bold march to become a credible collaboration and communication suite for businesses, Google Apps has encountered a frequent roadblock that has proven more vexing than expected to circumvent: good old Microsoft Outlook.

Google apparently underestimated how attached employees are to Outlook, the venerable e-mail program that epitomizes the "fat" collaboration and communication PC applications that Google despises and has vowed to eradicate from workplaces with its Web-hosted Apps suite.

[ Discover what's new in business applications with InfoWorld's Technology: Applications newsletter and Killer Apps blog. ]

Google announced Gmail For Your Domain -- the cornerstone for what would become Google Apps -- in February 2006, positioning its webmail service as an alternative hosted e-mail system for businesses vis-à-vis expensive and hard-to-manage internal messaging servers like Microsoft Exchange.

Although it gave Gmail support for POP3 (Post Office Protocol 3) and IMAP (Internet Message Access Protocol) so that end-users could synchronize messages with Outlook and other PC e-mail applications, Google resisted for years creating a specific Outlook synchronization tool.

For Google, adopting Apps involved accepting a new way of communicating and collaborating in the workplace, namely with Web-hosted applications, the software-as-a-service (SaaS) model that it views as the future, versus what it considers the passé, desktop-centric Outlook and Office.

In addition to POP3 and IMAP, Google also developed its Gears browser plug-in for providing offline access to Apps components like Gmail and the Docs office productivity suite.

Yet, even when given the possibility to use Gmail as an e-mail front end with and without an Internet connection, enough workplace users bristled at the thought of giving up Outlook.

Apparently, the resistance became more strident as Google has tried to market Apps to larger businesses, those with 1,000 or more end-users.

Last month, Google unveiled, rather surprisingly, its Outlook synchronization tool for Apps, spinning the occasion as a happy one, when in fact it could as well be viewed as a capitulation, a concession of defeat.

Google has found out that, yes, many companies are happy to ditch Exchange for Gmail if it means saving money and eliminating the grief of maintaining Exchange in-house.

However, and maybe to a degree unexpected by Google, it also discovered that many companies consider it a deal-breaker to lose the functionality that the Outlook-Exchange combo provides, thanks to the deep links that exist between this client-server tandem.

So Google embarked -- probably grudgingly -- down the path that other e-mail vendors have traveled with little success: trying to replicate the Outlook-Exchange experience with their back-end e-mail server and Outlook. Here was Google apparently getting dragged into the Microsoft way of doing things, creating -- gasp! -- a piece of PC software: an Outlook plug-in. The problems and complaints started immediately.

Right away, industry analysts cautioned CIOs and IT managers to examine the Google tool closely, warning them that it couldn't fully replicate in Gmail the functionality of the Outlook-Exchange combination, lacking basic features like the ability to synchronize Outlook notes and tasks, for example.

Barely a week after the tool's announcement, Google acknowledged it had several embarrassing bugs, including that it broke Windows Desktop Search, which is used to search Outlook data.