One of the biggest weaknesses of Microsoft Outlook has been the search feature. It takes so long for Outlook to search that the feature is almost useless.

Searching is not a hard problem, and a lot of plug-ins sprang up to solve this problem. Lookout was one of the best. It just works. Searching five years of accumulated email takes less than a second. Indexing is done quietly in the background and never slows down your system. Suddenly email is useful again.

So what happens? Microsoft buys Lookout. That’s nice, good for them.

But look more closely at the Q&A:

Q: Why can’t I download Lookout anymore?

We will be focusing our efforts on integrating our expertise and working on next-generation technologies.

Huh? What’s going on?

Q: What is Microsoft going to do with Lookout? …

The existing Lookout product will no longer be available, but its technology will be part of an exciting vision that MSN has for delivering new and innovative search services.

MSN?! Lookout is going to be part of MSN? What about Outlook?

Our vision is to take search beyond today’s basic Internet search services to deliver direct answers to people’s questions, and help them find information from a broad range of sources.

What? What the hell does this have to do with searching email? Could Microsoft have possibly bought Lookout just to shut them down? Even at my most paranoid, I can’t for the life of me figure out why Microsoft wants searching in Outlook to be worthless. Maybe just Hanlon’s Razor: “Never attribute to malice that which is adequately explained by stupidity.”

Update: They figured it out on the discussion group. Lookout is using an open-source component for searching, which Microsoft can’t redistribute. The only part of Lookout that Microsoft allegedly cares about, the search engine, is released under the Apache license. The only part of Lookout which Microsoft can use is the Outlook integration, and they don’t seem to care about that. Methinks this is one of those “HR Acquisitions,” wherein Microsoft buys a company for a few bucks because it’s the only way to hire someone they want.

About the author.

In 2000 I co-founded Fog Creek Software, where we created lots of cool things like the FogBugz bug tracker, Trello, and Glitch. I also worked with Jeff Atwood to create Stack Overflow and served as CEO of Stack Overflow from 2010-2019. Today I serve as the chairman of the board for Stack Overflow, Glitch, and HASH.