Google warns of issues with its Outlook sync tool for Apps

After promising that people can use Outlook "seamlessly" with the Gmail component of its Apps suite, Google is toning down those expectations.

A week after launching with great fanfare its Apps Sync for Microsoft Outlook, Google has addressed a number of shortcomings with this plug-in.

In a blog posting Tuesday, Google listed some popular Outlook add-ons and features that remain off-limits to Apps, even with the new sync tool.

"Unfortunately, some plug-ins don't yet work with Google Apps Sync for Microsoft Outlook, and we wanted to take this opportunity to highlight a few of the more common ones: Microsoft Office Outlook Connector, Acrobat PDF Maker Toolbar, Outlook Change Notifier," reads the Google posting.

To continue using any of these plug-ins, users have to uninstall the Google sync tool.

In addition, Apps Sync for Outlook doesn't play well with programs that interact directly with the Outlook data file, such as Windows Desktop Search and PGP.com's encryption plug-in.

Specifically, Windows Desktop Search will not properly index Google Apps Sync data files.

"So in order to stop indexing from running indefinitely, the Google Apps Sync installer disables it. We recommend using the default Outlook search," Google said.

Once again, to re-enable Windows Desktop Search for Outlook data files, users have to uninstall the Google sync tool, but there's a caveat: People using version 1.0.22.1945 or lower of the Google tool must first install the latest version and then uninstall it to re-enable indexing.

"We're working with Microsoft and other partners to help fix these issues and support additional Outlook features like multiple calendars. We'll keep you posted on our progress," Google's posting reads.

On Wednesday, Microsoft posted its own take on the Outlook search problem in an official blog, characterizing the issue as "a serious bug / flaw" in the Google tool.

"The installation of the Google Apps Sync plug-in disables Outlook's ability to search any and all of your Outlook data," reads the Microsoft post.

According to Microsoft, the problem is that the Google tool modifies a registry key that disables Windows Desktop Search's ability to index all Outlook data and make it searchable, not just the Outlook data that gets synchronized from Gmail.

"Because Outlook search relies upon the indexing performed by Windows Desktop Search, Outlook search functions are broken as a result," Microsoft said.

Contrary to Google's recommended remedy, Microsoft maintains that uninstalling the plug-in may not fix the issue and that the way to solve the problem is to change the registry key that was modified. Microsoft offers a step-by-step explanation of how to do this in its blog post.

Microsoft is also warning of another issue: Users who have the Microsoft Office Outlook Connector installed to synchronize Hotmail with Outlook will see an error message after they install the Google plug-in.

The error message, which warns that "some functionality will be disabled," is triggered by another registry key that the Google tool modifies and that is used by the Outlook Connector.

"When confronted with this error message, we recommend that users click 'Yes' to enable functionality. The Outlook Connector will then continue to function normally. The Outlook Connector will reset this registry key to the correct value," reads Microsoft's posting.

Last week, several industry analysts recommended that enterprises do their homework regarding the new sync tool, because it can't fully replicate in Gmail the experience of using Outlook with the Exchange server.

The Burton Group's Guy Creese pointed out in a blog post that the Google plug-in currently doesn't support Outlook features like tasks and notes, and that IT managers should tread carefully if they have special filters and custom templates in their Outlook deployments.

"For workers wedded to using every feature in Outlook, the Google solution is still insufficient," Creese wrote.

In a research note, Gartner analysts Matt Cain and Tom Austin said that companies that use Exchange and are considering moving to Apps' Gmail should first do a "stress test" of the sync tool and then do "a widespread pilot."

"We expect that Sync for Microsoft Outlook will have incomplete functions and that users will resist moving from Outlook to the Gmail client, thereby pressuring Google to fill in the functional gaps," they wrote.

While these functional gaps shouldn't automatically disqualify Gmail, IT managers should carefully consider them while making a decision, Cain and Austin said.

In an interview last week, Eron Kelly, senior director of the Microsoft Business Online Services Group, said Microsoft expected Exchange users to be dissatisfied with the feature gap when using Outlook with Gmail.

"This will just further reinforce in the eyes of customers and users that the Outlook experience is best fully replicated feature by feature in Exchange," Kelly said.

Kelly invited Google to consider becoming a hosted Exchange provider in order to get around the feature-gap issue. "We'd be happy to help Google do that. We have a great partner program."

Regarding the view that Google is increasing its competitive pressure on Outlook and Exchange, Kelly noted that Google is but the latest vendor in recent years to support Outlook connectivity, joining Novell, IBM, Oracle and Sun, among others.

"This is Google falling in line with the general trend of the industry," he said. "This is an example of further reinforcement that the Outlook experience is the premier and preferred experience for e-mail users."

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