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.

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 pass é , 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.

While Google scrambled for a fix, the Windows Desktop Search workaround sounded like an IT manager's nightmare: Uninstall the Google tool, unless you had version 1.0.22.1945, in which case you had to first install the latest version and then uninstall it to re-enable indexing.

Over at Redmond, Microsoft posted its own take on the problem in an official blog, characterizing the issue as "a serious bug / flaw" and overruling Google's workaround remedy. Uninstalling the Google tool wouldn't solve the problem, Microsoft said, providing step-by-step instructions for adjusting affected registry keys.

It took Google two long weeks to deliver the fixes for the search problem and other bugs.

Bill Pray, a Burton Group analyst, thinks it was a strategic mistake for Google to build the Outlook sync tool. Google will never be able to offer full parity with Outlook-Exchange, so die-hard Outlook holdouts will never be happy, he said.

Meanwhile, Google will spend significant resources and effort not only to increase the plug-in's capabilities, but to also keep it up-to-date with the latest Outlook patches and upgrades, Pray said.

"It will take Google a lot of time, maintenance and continued effort to maintain the interoperability," Pray said.

A better strategy for Google would have been to play to the strengths of the Apps suite and of Gmail in particular, betting on winning the support of the new generation of enterprise end-users, he said.

"Strategically, it costs more than it is worth to keep that Outlook connector working well than it is to compete on the strength of your own e-mail client [software] alternative," Pray said.

Prior to the launch of Apps Sync for Microsoft Outlook, Google was on the offensive, finding new ways to compete against Outlook by highlighting the differences between the Microsoft fat client and the server-centric, hosted Gmail.

"What Google will find is that while it will initially satisfy some demand with the Outlook connector, the connector will ultimately fail against the enterprise expectation that it work perfectly," Pray said.

People joining the workforce increasingly are comfortable and familiar with webmail services like Gmail, a trend that is organically reducing Outlook's appeal, he said.

By bending over backwards to accommodate Outlook holdouts, Google is weakening its case for the use of Gmail and Apps, Pray said.

Google holds a different view. The goal for the first version of Apps Sync for Microsoft Outlook was to meet "90 percent to 95 percent" of Outlook users' needs, which was accomplished, said Rajen Sheth, Google Apps senior product manager.

That includes the synchronization of e-mail, calendar items and contacts between Outlook and Gmail in "much the same way" as it works between Outlook and Exchange, he said.

While acknowledging that the tool doesn't offer full feature parity right now, Sheth promised that Google will extend its functionality aggressively.

"As you know, with Google, our first release is never our last release. We have a strong philosophy of getting something out there in the market that is strong and meets the needs, but then continue to iterate on it to add more and more functionality," Sheth said.

"You're going to see us do that aggressively with this product, just like we do with everything else. We'll continue to add releases to it, to add features, to make it better and better and go from 90 [percent] to 95 percent to close to 100 percent of the use cases," Sheth added.

Many people embrace Gmail's end-user interface when their companies adopt Apps, but companies of all sizes have vocal contingents of workers with a deep attachment to Outlook, for which the IMAP synchronization falls short, he said.

"There's a specialized experience that Outlook users have when using it with Exchange Server, and we wanted to make their experience with Google Apps to be as close as possible to that experience," Sheth said.

Google remains convinced that what it views as the benefits of the Web-based Gmail user interface will continue to be recognized in workplaces and will win converts even among Outlook die-hards.

Outlook loyalists can be found even in places that help companies adopt Google Apps, such as systems integrator Epicentro in Milan, Italy.

Epicentro provides Apps implementation services and has also used the suite internally since 2006, when it migrated from Exchange to Gmail. After several years, it still has "a few active users" of Outlook, said Mauro Ginelli, a Google Enterprise Applications specialist at Epicentro. After testing the plug-in, Epicentro plans to install it on its Outlook users' computers.

Ginelli thinks Apps Sync for Outlook will help convince potential customers to switch from Exchange to Apps. It gives Outlook users synchronization for e-mail, calendar and contacts, and can smooth out a progressive migration to the Gmail interface, as opposed to sudden and forced transition, he said via e-mail.

Rob Ardill, IT consultant at Metro Wireless and Networking in Adelaide, South Australia, also foresees that Apps Sync for Outlook will help him convince clients to give up Exchange for Apps, but believes that Google needs to take the product farther.

"If Google is serious about stealing Exchange customers, then they must offer native 1:1 features. This offering really targets those who have considered defecting to Google Apps and didn't want to jump without basic Outlook integration," he said via e-mail. "Those looking for more advanced features will certainly stay with Exchange."

It thus remains to be seen whether Apps Sync for Outlook will be a successful endeavor or a futile attempt to beat Outlook at its own game.