Email smackdown

When Gmail first appeared on the scene in 2004, I had mixed reactions. I had grown to love Apple's Mail.app, and it was going to take a lot to get me to let go. But a few months later, it was obvious that Gmail was the Next Big Thing™. Heck, invitations to the beta test were selling on eBay for 60 bucks. I had to see what all the fuss was about. As big a fanboy as I am for all things Google, I'm an even bigger fanboy for all things Apple. This was destined to be a tough match.

As of this month, I've been using Gmail as my primary email client for just over a year. Here are my thoughts.

Spam Filtering

One of my college professors said, justifiably, that the purpose of mass media in the modern United States is to deliver an audience to advertisers. So it might be said that the purpose of email is to deliver recipients to spammers. I can't imagine spam is very effective any more; most people have been trained to detect a sales pitch over years of bombardment, no matter how they try to misspell Cialis. However, that doesn't seem to prevent spammers from spamming. So an essential task of any mail-handling program is to weed out the product pitches, seedy solicitation, and financial fleecery.

Both programs have very good spam filters. Mail's spends some time in a "Training Mode" where it keeps spam in your Inbox, but depends on you to tell it whether it's correct in marking it as spam. Once you feel confident it's sorting out the spam, you can take it off training mode and put it on automatic. (*sniff* They grow up so fast, don't they?) The buzzword for that, back in the days when it was a shiny new feature of Mac OS X 10.2, was "adaptive latent semantic analysis." Say it in casual conversation, and you're well on your way to a wedgie.

Gmail, in contrast, has no learning period. It benefits from the daily feedback of millions of users, so even the most convincing spam is caught. In my entire year, Gmail let perhaps a dozen questionable messages through to my Inbox. Winner: Gmail.

Interface

It doesn't matter how smart the spam filters are if the program is ugly as sin. Fortunately, neither is. However, Mail.app allows you to customize the font and size of much of the text on screen. Like most OS X apps, it also lets you rearrange the toolbar buttons and add new ones at will. I found this especially handy, as the default arrangement is somewhat random. Gmail has an awesome interface considering it's just a web page with some fancy AJAX flavor. But web apps still have a hard time winning my love when they compete directly with old fashioned running-from-your-computer desktop apps. (Although Meebo is getting close.)

The fact that I have multiple email addresses also comes into play. Gmail offers no real way to separate one address's inbox from any other. Sure, I could set up a separate Gmail account for each address, but then I'd have to sign in and out all the time. Winner: Mail.app.

Ease of Use

One of my favorite Gmail features is one of their core concepts — you never have to delete an email. Just click Archive and it's sent off into oblivion until you look for it later. And boy is it easy to find it. Google's mail service has an excellent search feature — go figure. Ironically, this archiving business also got to be one of my biggest pet peeves about Gmail. Sure, you don't have to delete stuff. But sometimes I want to. They didn't have a Delete button until just recently. And that, dear readers, was ridiculous.

As much as the folderless, archiving, hassle-free Gmail concept appealed to me, I found myself missing the folder-like mailboxes that all other mail clients have embraced. Perhaps I'm old-fashioned, but hierarchical filing structures appeal to me. Plus, once Spotlight was introduced in 10.4, Gmail's spiffy search feature became a little less novel. Winner: Mail.app.

Integration

Gmail has an uphill battle on this one, because Apple and its army of iApps wrote the book on inter-application integration. But there was hope. Once the Gmail Notifier was released, it became possible to have all "mailto" links open a Gmail compose window. This worked reasonably well, but wouldn't work for attachments (photos emailed directly from iPhoto, for example). Also, Gmail had its own contacts, which could be imported from CSV files. Spiffy!

Not spiffy enough to match the powerful iApp integration, though. Mail autofills addresses from the Mac OS X Address Book, can automatically add event invitations to iCal, and even displays a buddy's online status from iChat. Having to keep my Gmail and OS X address books in sync was a hassle, so Mail.app won this battle by a landslide.

Access

Speaking of landslides, here comes one in the opposite direction. Like most desktop-based applications, Mail.app offers limited remote access. If I was away from computer, I could log into my domain's webmail, which was sub-par but did the job.

Gmail, on the other hand, is accessible anywhere by its very definition. It even allows mobile devices like Palms and cell phone to check mail at a special address and slimmed-down interface. Winner by a longshot: Gmail.

Import/Export

One of the scariest things when switching email clients is the prospect of having to move all your mail to the new program. Mailboxes frequently have to be exported and re-imported one at a time, attachments aren't guaranteed to come through, addresses are unlikely to transfer, and you can forget about any special flagging or labeling of messages that you did. Due to these things and the fact that there was no official method of getting mail from Mail.app to Gmail, I opted to start fresh on Gmail and not worry about any of that. If I needed something old, I opened up Mail.app, otherwise I stuck with Gmail. This worked well enough.

Getting mail back out the other way proved to be much easier. Gmail offers the ability to check your mail using POP, so it's just a matter of connecting Mail.app to the right server. Sent messages come through along with all the others, but that can be fixed with a simple filter. Winner: Neither.

Power Potential

As a card carrying member of the International Order of Computer Geeks, I love to soak up power tips, shortcuts, and advanced features of every program I touch. (For instance, did you know that on a Mac, you capture a screenshot of a given window to the clipboard by pressing Command-Shift-4, then pressing the space bar, then clicking the mouse on the window you want while holding Control? True story.)

I especially love keyboard shortcuts. During a typical day, I find myself avoiding the mouse for long stretches of time; so much so that I actually notice when a program makes me reach for it. Gmail made me reach for the mouse constantly. Now, it does have keyboard shortcuts, which is majorly impressive for a web interface, but it can't possibly match the keyboard-crunching power of a desktop application. I can switch to Mail, check for new mail, type and address a new message, send it, and switch back without touching the mouse. (That would be Command-Tab, Command-Shift-N, Command-N, [recipient's name], Tab Tab, [subject], Tab, [message text], Command-Shift-D, Command-Tab. Best when followed by a fit of maniacal laughter.) Winner: Mail.app.

Stability and Reliability

Like all desktop applications, Mail.app is subject to the imperfections that occur when ones and zeros collide. While the latest version is very stable, previous ones have been touch and go. Plus, if the amount of mail in any single mailbox gets higher than a gigabyte or so, it starts to get very sluggish and crashy. It's nowhere near as flaky as Microsoft Entourage and its tendency to turn into a pumpkin when the database exceeds 2 GB. But it's definitely not as rock-solid as Gmail. Winner: Gmail.

Bells and Whistles

Aside from its tight integration with the other iApps, Mail.app doesn't have that many bells and whistles. Gmail, on the other hand, has Google Talk chat built in. Unfortunately, it doesn't work with Safari, my browser of choice. It also has customizable RSS feeds in the form of "snippets," but I found myself turning those off after only a few visits. They definitely get points for trying, though. Winner: Gmail.

Security

I'll be honest: letting my email be stored permanently on some remote server somewhere kind of creeps me out a little. Google already has information about every website (because of their Web Search), business (Google Local), location (Google Maps), and person (the oft-forgotten Phonebook feature) in the world. And now they have everybody's email.

Also, sending secure encrypted mail is something I do every once in a while. As infrequently as I need it, it's nice to know that Mail.app can do it. Gmail, on the other hand, cannot. Winner: Mail.app.

The X Factor

In addition to all the above categories, a mail client must have a certain something else in order to really win my love. Let's call it je ne sais quoi.

Gmail gets points for being made by Google. This gives comfort to me, because I know it will continue to be developed, cool new features will keep coming, and it will integrate well with whatever goodies they offer (I'm eager to see how they tie it to the new calendar.) It also makes a very small footprint on the computer (doesn't occupy much memory) and isn't tied to any one specific operating system. It also has a neat notification system in the Gmail Notifier menu icon. Those are all good things.

Mail.app gets points for exactly the converse of those points. It's made by Apple, so I know it will keep getting new features and integrate wonderfully with the rest of my Mac. It does take up a bit of memory when running, but it has the snappy instant response of a real program rather than the delayed response of a website.

The bottom line here is that I want my mail to be tangible. I want to feel like I have control over every message, and I know exactly where it is and how to get it. If men in black masks jump out of an unmarked van and start running up my stairs, it's comforting to know that all I have to do is blow away my ~/Library/Mail folder, and they've got nothing. Nothing, you hear! Winner: Mail.app.

Overall

My final solution, and one I plan to continue using for the next year or so, incorporates all the best parts of both programs. I love the Gmail junk filtering and "never delete" concept, but I also love the tangible feel, customizability, and snappy interface of Mail.app.

Now, all of my email addresses forward to my Gmail account, so they can be spam-filtered and archived. Then I use Mail.app to check my Gmail account via POP. This way, I don't have to keep Mail.app open all the time, because the Gmail Notifier lights up when I've got something new. I also have the benefit of being able to use multiple hierarchical mailboxes, while still maintaining Gmail's flat storage as a backup. Score!

Winner: Both.