September 22, 2005

GMail vs. Outlook


There are two programs that computer users feel very strongly about:  their email client and their Web browser.

Computer users very rarely change any of these applications, and it takes more than features to overcome the inertia and sense of comfort that you have acquired after spending so many hours on either of these tools.  And even though the Web browser has a very low retention threshold (except for your bookmarks and your habits, you are not putting much at risk by switching browsers), it's quite interesting to see how many people are still using the very first Web browser they started using.

The email client is even harder to switch away from, because the amount of personal email that you have accumulated over the years is not just huge, it's also extremely personal.  Of course, there is also the added damage that your email address might change in the process, forcing all your friends to update their contact information for you.

With that in mind, it's not without a certain sense of excitement that I recently made the decision to switch away from Outlook to...  GMail.

First of all, let me get something out of the way:  since I work for Google, you might think my decision has a corporate side to it, but those of you who read my weblog regularly know that I am fairly pragmatic person when it comes to picking the most productive tools.  A year ago, I wrote a comprehensive comparison between Outlook 2003 and Thunderbird where I explained my decision to prefer one over the other.

I spent these past months using both Outlook and GMail in an effort to evaluate and compare these two tools.  Outlook sets the bar pretty high in terms of functionalities and convenience, but what eventually tilted the scale was my one-week vacation Hawaii last week.  More about this below.

Most of the Outlook pros and cons that I listed in the article above are still completely valid (I can't find one that no longer applies, actually), so I guess that one interpretation of my switch is the realization that the drawbacks of Outlook have finally reached a point where I no longer want to tolerate them, and also because GMail has slowly gained functionalities that I considered essential.  Overall, I still think that Outlook is more functional than GMail, but given the rapid pace at which GMail is evolving and the diminishing tolerance that I have for delays in my email reading, it still emerges as a winner.

There are basically three factors that eventually broke the deal for Outlook:  connectivity, spam handling and synchronization.


As I stated in the article above, Outlook is much more powerful and seamless to use with an Exchange server than with IMAP.  The IMAP support doesn't seem to have received any kind of improvement these past years (not really surprising) and not only does it lock up the interface very regularly, it's also extremely slow.  In contrast, GMail is always lightning fast, even on slower lines (I regularly use in over my GPRS cell phone and the delays are barely noticeable).

Spam handling

There are many anti-spam programs available for Outlook (I reviewed some of them here) and after a few evaluations, I had settled on SpamBully for Outlook, which is very good but also very slow.  As a consequence, running it on an Inbox that hasn't been updated for a week can take almost an hour.  Yes, it's that slow.  But it was so good that I didn't mind taking the hit.  GMail's spam filter has been absolutely terrific so far.


I access both my personal and work emails from a lot of different places:  work desktops, work laptop, home desktop, home laptop and sometimes even, from computers that I don't own.  This latter option is obviously not possible if you use Outlook as your main client, but even the first four types of accesses are problematic.  So far, I was dodging the issue by using Remote Desktop to log into my work machine, where my main Outlook client is always running.  While Remote Desktop is an outstanding piece of software, this technique has some serious limitations, mostly because of its bandwidth-intensive nature.

Finally, there is one thing that has always been very clunky with Outlook and to which I had somehow gotten used to (or rather, resigned myself to):  the address book.  Despite many efforts, I have never really understood why Outlook has so many places where it stores contact information (the Address Book, Contacts and the online cache for completion).  I have never been able to reconcile them or use them in a consistent manner.  As a result, not only were my contacts scattered left and right in all these places, it was also maddeningly difficult to create groups of email addresses (and also keep them in sync as I make changes to the individual email addresses).

Now, there is one added benefit that completed my conversion to GMail:  transparency.

In case you are not aware, you can start using GMail right now and you don't have to ask any of your friends to update their contact information for you if you don't want to.  This made possible by a critical GMail feature: "From masking". You can tell GMail to display all the emails you send from GMail as coming from another email address.  This is really what makes everything work so well, and it's a feature that was recently added.  To configure your From address, go to Settings / Accounts / Send Mail as.

Let's see if GMail keeps its promises (and if you are curious to try it yourself, email me and I'll send you an invitation).


Posted by cedric at September 22, 2005 01:37 PM

Last I checked, the From masking was not very useful as it inserted some "by way of" header into the mix which advertised that you were doing weird things with two addresses. Has that changed? If not, I didn't find the From; addressing to be effective enough for my tastes

Posted by: Ed Hill at September 22, 2005 03:16 PM

I quite like gmail but one annoyance is that you can only operate on one page of conversations at a time.

For example, I got out of the habit of archiving conversations and now I have thousands of them in the mail box.

As far as I can tell I can only archive 100 of them at a time. :-(

Posted by: Chris Richardson at September 22, 2005 03:48 PM

apples vs oranges.

Posted by: sam at September 22, 2005 03:56 PM

So when is gmail calendaring and resource sharing coming out. ;o)

Seriously, I'd love a webcal/ical in gmail people could subscribe to.

Posted by: Peter Morelli at September 22, 2005 05:16 PM

I switched from Outlook to GMail over a year ago. I'll never go back.

Posted by: Sean M at September 22, 2005 06:01 PM

Gmail rules. I love not hosting my own IMAP server.

Posted by: Bob Lee at September 22, 2005 08:50 PM

I don't think computer users feel very strongly about their browser. The average computer user feels about their browser like I feel about POTS local phone service: other companies to provide local phone service, I've heard about them, but I'm happy right here, and who knows what'll happen if I change?

A dollar says I'm the only one who posts to this blog who still has a POTS line at home.

I'm sure your article says much more but I got stuck by the first sentence.

Posted by: Robert Konigsberg at September 22, 2005 11:13 PM

I use Fastmail, which has everything you could want, but you do have to pay (only about $20 a year) but that means no adverts at all :)

Posted by: Rich at September 23, 2005 02:50 AM

The GMail spam filter is a MAJOR pain for me. I get virtually no spam in my gmail account, My ham to spam ratio must be 0.001% or something - low enough for me to not care about a spam filter, for now.

However GMail does give a lot of false +ves. I'd guess one a week. It marked 3 from the mailing list last week. So I have to constantly check my spam box for ham that I might have missed.

I'd really really like to turn it off, but I don't know how. Any ideas?

Posted by: Joe Walker at September 23, 2005 03:06 AM

I don't have from masking. I heard about the feature when it was intially trialled several months ago - and have been waiting for it ever since. I've just checked a second GMail account I occasionally use and it also doesn't have from masking.

Whatever happened to web clips and other features that some people got and others didn't?

I run Thunderbird and GMail constantly all day long. It turns out, I send most of my email from GMail. Why? Well, I can start, compose and send an email in less time. GMail is faster to start an email, faster to choose a contact and faster to send an email than Thunderbird.

Posted by: RichB at September 23, 2005 04:16 AM

Outlook is very popular in big firm. not at normal person side.

Posted by: xin zhao at September 23, 2005 01:09 PM

Although GMail is the best free web mail out there, I wish they would add IMAP (even if it is a pay service). And also (and more importantly) they should provide an option to disable their spam filter, especially when its likely to have false positives. I'd rather get spam than get false positives.

Right now, I run my own IMAP server with Courier/Fetchmail/Procmail/Spambayes which grabs my e-mail from my ISP-provided pop-mail account. I have never had a single false positive in the last year of using Spambayes (it splits spam into "maybe" and "definitely" and neither have had any false positives).

Using IMAP means I don't have to make the choice of what e-mail client I want to use, I can just connect with any mail client that supports IMAP, and even throw a web interface over it if I wanted to. The only problem being that I haven't found a good method of maintaining a server-side addressbook.

Since Gmail has pop3, I could have the same setup with a Gmail account, but the spam filtering is the main thing stopping me from doing this.

Though I have a choice of e-mail clients, after trying different ones out, I ended up using Thunderbird everywhere on all OS's, but if I find something better switching will be painless.

Posted by: N at September 23, 2005 01:27 PM

WSJ had an interesting comparison between the soon to be introduced upgrades to yahoo mail and gmail. Yahoo trumped gmail in every aspect. The thing that stood out in the review was the "arrogance" of Google in making some of the choices for Gmail. Couldn't agreee more.

Posted by: Vostok at September 23, 2005 05:01 PM

If you mask the from address - won't the reply go to the masked address rather than the Gmail address?

Posted by: Sony Mathew at September 28, 2005 11:12 AM

It all sounds good, but what's the point of masquerading tou From address if you can't retrieve the mail sent to this address?
As far as I can tell GMail cannot retrieve your mail from another POP server.
Am I missing something?

Posted by: Vincent at October 4, 2005 09:35 AM

Gmail has left conventional get by snail mail in the dust. Outlook and others are counter productive oldies. Why chop and change mail clients if you can fly with Gmail. Adds are forgotten easily and go by un-noticed, you really have to look for them.

Gmail Rawks!

Posted by: Marius Beukes at October 4, 2005 03:26 PM

I have my own imap serverwritten in c,c++) on linux 9.0 that is working properly
at command prompt but not with outlook.

Posted by: parikshit at November 20, 2005 10:49 PM

Three phrases should be among the most common in our daily usage. They are: Thank you, I am grateful and I appreciate.

Posted by: at February 9, 2006 11:18 PM

My employer makes us get our official email in outlook but i have noooo idea how outlook works (im sort of a computer ditz!) I do know how to use gmail though and love it. I was wondering if you knew of how to forward messages from outlook into gmail. I found i did the "rule" setting and was able to foward it into gmail but all the emails say they are from me. I was wondering if anyone had any tips. I would LOOOOOVE you forever if you could help me!

Posted by: Ashley at March 14, 2006 09:54 AM

You can forward your emails from your server if the emails are going to
It is done in the cpanle of the server that hosts your email account and/or website.
I have set this up on gmail for my business partner and it works fine.
The email goes into gmail and is addressed from the sender.

Posted by: jason at May 9, 2006 05:18 PM


Posted by: javad at October 2, 2006 11:42 AM

OK, I realize this is an old post, and since I'm only semi computer literate I might be in the wrong forum, but you might be the right person to ask.

I work from home and use Outlook (2000) as my client. I've set everything according to the instructions at GMail so that my e-mail address shows up as, but it seems some people (apparently, those using Outlook 2003) see my e-mail address as:

Person [] On Behalf Of Person

Is there any way to fix this so that only my corporate address shows up?

Thanks in advance.

Posted by: Greg at February 12, 2007 01:50 PM

My name is Grace Yohai and since we have our own LAN, I use yohai msn. Can I continue to do that if I change my e-mail browser from Outlook to G-Mail? (I think I can but I'm not sure.)

Thank you

Posted by: Grace Yohai at March 30, 2009 06:48 AM
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