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.