Gmail launched in 2004 and has matured each year, but Microsoft Outlook (with Exchange) is still the most popular tool for accessing email. Comparing the two side by side, is it time to jump ship from either platform? Let's find out.
This comparison below is based on Microsoft Office Outlook 2007 with Microsoft Exchange Server 2003 and Google Apps for your Domain's free version of Gmail.
There are many differences between the two products in terms of how they can be configured and the type of workflow that they support. I'll go through each area of difference below, comparing and contrasting. At the end, you'll find an overall comparison and some recommendations.
Search
Microsoft greatly improved its search capabilities with Outlook 2007. This is probably the most important reason users of earlier versions would upgrade—because, let's be honest, searching in Outlook used to take hours to perform. Their search is now powered by Windows Desktop Search and does a good job of returning results fast.
But Gmail is still much faster. And as an added hassle, if Outlook ever returns incorrect or incomplete search results you have to dig into the settings to tweak or rebuild your search index, hoping that you can fix the problem.
One advantage of Outlook search is that it searches within attachments. Google Desktop Search would accomplish this if you used a separate email program (even Outlook!), but the Gmail web interface does not. Still, the inability to search within attachments is a small price to pay for the superior speed and accuracy of Gmail's search.
Search Verdict: Gmail wins for a faster and more reliable search. Outlook is just a step behind with full attachment search.
Folders vs. Labels: How To File Messages
Gmail departs from the traditional folder tree by using "labels," which are essentially tags. What's nice about labels is that one message can be assigned multiple labels (effectively making it appear in what seem to be separate folders) without having to copy the message. For instance, if a message relates to both "family" and "work," then with Gmail you can mark it with both labels and find those messages in either of those label-folders. In a traditional tree, you would have to choose only one folder (or duplicate the message).

Outlook has always had categories, which behave similarly. In version 2007, Outlook created a faster system that used color-coded/named categories and Search Folders to perform nearly the same functionality as Gmail. Most people are not aware of this feature because it's less noticeable than the Outlook folder tree and would require setting up search folders for each category to function like Gmail labels. However, since categories have no relationship to the folder location of an item they're not a complete replacement for the folder tree.
On the surface, labels seem superior to a folder tree—after all, tags are the preferred method of identifying data on many new web sites. There are a few problems with labels, though:
- There's no such thing as "sub-labels." As such, if you decide to use Google like a folder tree, you'll quickly discover that the hierarchy is only one-level.
- There is no drag and drop functionality in the Gmail web interface (most likely since applying a label isn't necessarily moving it from one label to another).
- Gmail's labels are not 100% compatible with IMAP support. They're mostly compatible, but some people (like me) may run into synchronization issues.
Even with these slight limitations, Google was wise to eschew the top-down methodology to which many of us have grown accustomed. Since Gmail's search is very fast, the need for finding items by how they've been filed becomes less important.
In Outlook, a label-like feature is available but harder to access. It has additional filtering and organizational capabilities, but most users might not dig that deeply into the software to find them, especially since in Outlook one still has to work with the folder tree to move items out of the Inbox.
Folders vs. Labels Verdict: Gmail wins for a simpler, generally more flexible approach.
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