Google Mucks Up Outlook

Last week, when Google (GOOG) launched a plug-in that allowed business customers to switch to Google Apps while retaining the Microsoft Outlook interface, industry watchers regarded it as Google's most aggressive effort yet to challenge Microsoft (MSFT) in the enterprise market. After all, Google Apps is cheaper and easier to run, and Microsoft's clients only seem to stick with the company because change is scary.

Now we know just how scary change can be. Today, Microsoft announced on its blog that Google's new Outlook plug-in has a "serious bug/flaw" that could disable key Outlook functions. According to Outlook Product Manager Dev Balasubramanian, installing the Google Apps synch plug-in changes a registry key and disables the ability to search Outlook data. So if you need to find that old e-mail you sent about your company's first-quarter profits, good luck poking around your archives for a few hours. Moreover, Balasubramanian adds, uninstalling the Apps plug-in won't fix the problem; only manually changing the registry key back will restore the search ability.

In addition, the plug-in appears to flash an "error" message for people using Microsoft Outlook Office Connector, but it's no big deal; the message itself is the error, and people can just click yes and get back to work. "We have brought these issues to Google's attention, and have offered to work with them to find a resolution for our mutual customers," Balasubramanian writes. "As soon as this is done, we will publish more information."

Google's main obstacle to cracking the enterprise market is a corporate culture that values the familiar, and nothing is more familiar than Microsoft Outlook. Hence Google's stab at keeping the feel of Outlook while swiping the underlying infrastructure. But with this one gaffe, the company has merely reinforced corporate fears that ripping out the guts of its tech operation and replacing it is too much of a headache to be worthwhile. It's a rare misstep for a company known for its attention to detail.

Update: Google spokesman Andrew Kovacs has written to note that users of the new Apps Sync plug-in can still search Outlook data by using Outlook's default search, "and we're working with Microsoft to enable search with Windows Desktop Search as well." Also, it appears that uninstalling the plug-in should fix the problem after all. If you want a more thorough accounting of these bugs, you can read all about it here.