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Web Worker Head to Head (to Head): Gmail, Hotmail and Yahoo! Mail

May 11th, 2007 (12:00pm) Judi Sohn 37 Comments

Last week, we introduced our little cage match feature by pitting iGoogle against Netvibes. This week, we’re setting up the battle of the free email.

Thanks to the new web, webmail has grown up from the slow, clunky interfaces of the 90s. It was what we used to quickly check email on the road or when our desktop client was acting up. We wouldn’t dream of ditching a stand-alone application for our email needs (some of us still won’t). Now, it’s entirely possible to not only have all our email communications be accessed through a browser, but we can be more productive working that way than if we were tied to a single client on a single machine.

Google’s Gmail broke the mold with its unconventional interface and then unheard of 2GB of mail storage. Microsoft and Yahoo! have tried to swing back against Google with their answers to web-based free email.

How do they stack up? Read some opinion and then weigh in with your own rounds in the comments.

Windows Live Hotmail:

Hey! You in the back…put down that tomato! Even though it’s from Microsoft it may not be entirely evil. Let’s give it a fair shake before we throw it out of the ring.

Hotmail has been around forever. It’s the web interface that’s “new.” Windows Live Hotmail offers 2 GB of storage space and has just launched its fancy-schmancy web client. Soon Microsoft will unveil a desktop client version that’s meant to replace Outlook Express as the stand-alone freebie. Like Yahoo!, Microsoft assumes that a desktop client is what people really want and has gone to great lengths to try and reproduce that look & feel. Which is okay if you like your email surrounded by colorful, animated ads. Lots of them. In fact, ads take up nearly as much space as email.

Microsoft doesn’t offer POP or IMAP access to email. Instead, they’ll soon have a plug-in that allows you to check Hotmail from Outlook. Not quite the same thing. Like Gmail, you can set an alternate “reply-to” email address. And like Gmail, you can’t hide the fact that you’re using a free email account to send the email, as the message will appear in the recipient’s box as “From: email@domain.com on behalf of myfreeaccount@hotmail.com.”

Out of the box, the spam filter isn’t terrible. It catches most obvious junk and holds it in a folder where it’s purged after 5 days. For mobile access, Microsoft offers the ability to get SMS text messages alerts for important messages and a Windows mail mobile client (Windows Mobile OS only, natch).

Had Microsoft/Hotmail seriously put on the webmail gloves a few years ago, maybe this would be a contender. Drag & drop and pages that update without refreshing aren’t features in and of themselves. They’re what we expect nowadays. If you’re someone who has years of history with a @hotmail.com address, then the new Windows Live Hotmail is going to be a nice change. The rest of us can move on to the next challenger.

Yahoo! Mail

Yahoo!’s mail beta has been around for a while now, offering 1-2 GB of storage space now offering unlimited email storage. Like Microsoft, Yahoo! suffers (and suffers and suffers) from ad overload. Especially on the “Home” page which has news in a tiny box surrounded by ads. Also like Microsoft, Yahoo! mimics a desktop client interface with panels and sortable columns.

Some of Yahoo!’s best features require a paid upgrade to Mail Plus. This gives you the full 2 GB of storage space, more flexible POP features and gets rid of the ads. Getting rid of the ads may be worth the $19.99 per year fee alone. Even in the free service, Yahoo! attempts to smoothly integrate its other services into its webmail client. Calendar and photos are easily accessed when appropriate. Yahoo! IM is built right in (new stand-alone web-based messenger was recently launched). There is an easy vacation auto-response setting (as is in Gmail) and RSS feeds built-in to the interface. Gmail and Hotmail send you off to separate pages in their network to read feeds.

What Yahoo! mail needs is better spam filtering in the free version. Of the three webmail clients, Yahoo!’s Spam Guard is near useless leaving almost as much junk in the inbox as it moves to the spam folder.

Yahoo! was early out of the gate with some nice features, but has since lagged behind. Those who embrace their @yahoo.com email address are probably paying for it. For the rest of us, the free web client is nearly crippled with poor spam filtering and ad overload.

Gmail

Gmail made it cool to have free webmail. Perpetually in beta, Gmail was the first webmail application that asked, “what’s so great about a desktop client, anyway?” No 3-panel split view. Email is organized by conversation, not date or subject. Desktop email applications push you to organize your email into folders, otherwise finding that email from Sally that she sent on the 15th asking about a meeting on the 20th would be a bit of a chore. With Gmail’s killer search features, if it’s in there, you’ll find it easily with a few keystrokes.

Google doesn’t give you a lot of control over the spam filter. But then again, they don’t have to. It works well from the first punch. Most of us don’t even bother looking for false positives anymore. Gmail also doesn’t give you much control over how your inbox is presented. Do you want your email sorted by conversation, or sorted by conversation? The crowd will roar if Google ever lets you sort messages by date, sender or subject. Not likely to happen. Gmail’s conversation view is what sets it apart.

Since its initial launch, space was increased from 2 GB to nearly 3 GB and growing. You can check your Gmail account from nearly any POP email client, on or offline. You can check other email accounts from the Gmail interface. Unlike Yahoo! or Hotmail, you can access Gmail from a simple HTML interface inside any mobile browser (plus download a stand-alone mobile application). This doesn’t even touch all the other ways you can hack Gmail to work with other applications and services. If you want your email flexible, Gmail throw a punch so powerful Microsoft and Yahoo! are still struggling to come to their feet.

Google is trying to do a better job integrating their services, but here they take an uppercut. While you can add a calendar event right from Gmail if it detects that’s an appropriate action from the content of the email, it seems silly that one has no control over where and how that functionality pops up. There is no sign of Picasa when you receive an email with an image attachment, and only recently did Google add the ability to open document attachments in Google Docs & Spreadsheets.

Thankfully, no animated, annoying ads in Gmail. Yes, there are ads and plenty of them. But all the ads are text-based and easier to tune out. Email is the predominant visual in the Gmail interface, not advertising, as it should be.

The winner comes down to a decision. If you want flexibility, and you’re not in love with a standard desktop client interface, then it’s Gmail by a mile. On the other hand, Windows Live Hotmail and Yahoo do have some smooth moves in their favor not to be dismissed. In the end, since web workers tend to value the functional and customizable over the pretty and rigid, this round goes to Gmail. Now it’s your turn…

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37 Comments Post your own comment

John B says: May 11th, 2007 12:48pm

I would have to disagree with you on the Hotmail assessment. My biggest gripe is it’s lack of really good support for non-IE browsers. Until recently it crashed Firefox for me whenever I used it, (although before commenting here I checked and so far my browser has not crashed). Also, for me, about the only things the junk mail filter classifies as junk are password reset notices when I forget a password. Better than 95% of junk mail makes it into my inbox. However, I only use the Hotmail for personal correspondence.

Gmail, on the other hand, I love. I use Google Apps for all my business-related E-mail and keep it running most of the time. There isn’t really much to say about it because it’s so good.

I have a yahoo account that I don’t use, but it looks cool. I’m just happy with Gmail for business, and am not willing to try to get people to learn a new Yahoo address when they know my Hotmail for personal correspondence.

Judi Sohn says: May 11th, 2007 1:00pm

John, Firefox never crashed on me the entire time I was was testing it, which I have to be honest was only in the last week. I had a particularly spammy account forwarding to Hotmail (and Yahoo) for a few days to test them out, and Hotmail did a decent job of catching the junk. Nowhere near as good as Gmail, but nowhere near as bad as Yahoo.

Geof Harries says: May 11th, 2007 1:11pm

What about .Mac? In my view, spam filtering is top notch, the webmail client is highly attractive and very usable, plus it’s IMAP, so the app auto-syncs with your desktop client. Against this competition, .Mac slays them all.

Deepak says: May 11th, 2007 2:06pm

Yahoo has spam filtering? I would never have guessed. Gmail by a mile and then some at this end.

Bill says: May 11th, 2007 2:33pm

Agree, hands done, Gmail is the winner, and then add Firefox with Greasemonkey into the mix and it is a TKO!

trucex says: May 11th, 2007 2:45pm

In response to Geof:

.Mac costs $100 for a year of service, includes only a GB of storage, and limits you to 10GB of transfer. For comparison, I can purchase a full-fledged web hosting solution at textdrive.com (top-notch) for the same price and receive 5GB of disk space, 15GB of transfer, and as many email addresses as I want that can all be accessed via IMAP. Plus I get access to their Strongspace secure backup and I can have 5 databases. Why would I want a .Mac address again?

Geof Harries says: May 11th, 2007 2:56pm

Trueck - I actually have a full-featured VPS hosting account (Media Temple DV) but it comes with Squirrelmail as the default webmail client. Usable, but that’s it where the fun ends. On the topic of Textdrive, I’ll be honest, their uber geek admin panels are just plain ugly. They’re also hard to use and poorly integrated. TextDrive is way behind here.

In the end. this argument isn’t about capacity or technical features. It’s about webmail experience and functionality, which I don’t mind paying the extra cash for with .Mac.

Randy Stewart says: May 11th, 2007 3:53pm

While I agree that Gmail wins this contest handily, Yahoo would win, if they interface they have created wasn’t so… damn… slow…. I’ve been a POP Yahoo! mail user for years and email address lock-in has got me there.

One word on Gmail’s spam filter, though. I’ve found that it works well in fits and spurts. Unfortunately, I disagree with you completely on the false positives here. Where Yahoo! seems to err on the side too much inbox spam, Gmail errs the other way. I get false positives in my Gmail spam filter weekly.

Cheers,
Randy

Head to Head between Yahoo! Mail, Gmail, and Hotmail | My Mother Married A Felon says: May 11th, 2007 3:58pm

[...] Web Worker Daily has a head to head post comparing Yahoo! Mail, Gmail and Hotmail. Pretty interesting… [...]

Matt Stefani says: May 11th, 2007 4:01pm

Gmail is THE BEST free application (web-based or desktop) ever. Period. Hotmail or Yahoo do not even come close. Enough said!!!

Mike Torres says: May 11th, 2007 4:03pm

Good and fair write-up.

I would add two things to the Hotmail section that I think are pretty cool:

* Anti-phishing / suspicious mail. This is something that Hotmail does incredibly well and 280 million people (or at least the percentage who aren’t email experts like web workers are) will really benefit from this.

* Native Outlook synchronization. This may not be a big deal to folks who use Firefox all day, but an incredible number of people sit in Outlook day-in and day-out at work. Having a full-on Outlook Connector (contacts, mail, etc.) that essentially mimics most of the functionality of Outlook+Exchange Server is seriously compelling. This of course isn’t POP3 - it’s full sync so any change (i.e. moving a mail from folder A to folder B) gets replicated back to the service.

The Windows Live Mail client coming out later this month does this too - and since a lot of people don’t have multiple machines to worry about, a simple download gives you all the richness of a client + the use of the service for when you aren’t at your primary machine. It’s really pretty cool.

You can also access most of Hotmail’s functionality from *any* mobile phone (not just Windows Mobile) via http://mobile.live.com. But again, full synchronization and “push” mail like Outlook+Exchange occurs with Windows Mobile devices.

Yes, I work for Microsoft. But still… :)

webonics says: May 11th, 2007 4:04pm

My vote is for Yahoo!. However, I am a Plus member so there is a difference from the free version. The interface is smooth, attractive and very interactive. While I like using a tag cloud for photos on Flickr, events on Upcoming and favorites on Del.icio.us, I was turned off by its use in Gmail. I also like how Yahoo! integrates its other services into the client such as today’s addition of the Yahoo! IM as well as long-standing integration of calendar, photos, etc. At the end of the day, everyone has a different approach to the way they work and the different offerings work best for different people.

Julia Demchenko says: May 11th, 2007 4:25pm

I am using Gmail for a long time now and since Google Apps appeared I have all emails in one place. I really like Gmail design, well, minimum of it actually. That what makes Google services great! And thread grouping is a very good idea, took me a while to get use to it, but now it’s seems like the only right way.

nomadicalloy says: May 11th, 2007 8:41pm

gmail is good, but cannot access it from work.

links for 2007-05-12 --Stewtopia says: May 12th, 2007 1:25am

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GigaOM » GigaNET Weekend Reader says: May 12th, 2007 6:59am

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FiZ says: May 12th, 2007 7:19am

GMail wins by leaps and bounds.

Yahoo and Microsoft? Trying to replicate the typical desktop email interface is NOT a great idea. Using next-gen techniques to replicate the crap it was meant to replace is not advancement. Besides, every non-techie friend that I’ve switched to GMail loves it even without knowing how to use the power tools in it.

I’m not saying that GMail is perfect in every way, but they’ve done the best job at actually trying to make email more efficient and intuitive.

Mike says: May 12th, 2007 9:26am

I have 21 email aliases. After a long time I changed that to forward to 2. I then set these up on gmail after using my Apple Mail program on my Macbook. I have to say I will never go back. Span filtering is amazing. Sort by conversation is the bomb and the portable phone client is brilliant. Hands down. I even managed to change my wife from Yahoo without any complaints.

ringer8 says: May 12th, 2007 10:58am

what’s the deal with windows vista not allowing for sending web pages and links directly…other than copy and paste after opening my e-mail is there an easier way

katm says: May 12th, 2007 12:02pm

I have and use all three on a regular basis. As far as spam filtering goes, gmail wins for me hands down. I can count the number of spam messages that have gotten through to my in-box in the last 18 months on one hand. Yahoo (for me) is second best. For a while it was catching everything and only had a few false positives. Lately a few spams have gotten through. Marking them as spam seems to take care of it for the next time. Very few real emails hit the spam folder either. Hotmail has been abysmal. I get more misclassified mail than the other accounts combined (4 gmail/2 yahoo). Marking things as spam/not spam is useless. They continue to show up in the wrong place. And some stuff I’ve been marking as spam for months. In the old Hotmail interface, you couldn’t report a bunch of things as spam. You had to do them one at a time, which was a pain when having dozens of messages to mark. I’m not sure about the Windows Live version. I just switched over yesterday.

When I tried it a few months ago, I found the Yahoo beta to be really slow (using Firefox) so I switched back to whatever they’re calling the old view. And I just checked again, and it’s still painfully slow. There’s a lot of wasted screen space on it too. Interestingly enough I changed over the the new Hotmail look and found it snappier than the old one. I like the interface better as well.

The thing that makes gmail the most useful for me is using it to handle discussions on email lists. I alpha test software. All of the discussions go through their email list (why we have forums, I’ll never know). Being able to keep all of the 5.9.10 (or whatever version number) emails in one thread makes it so much easier. And gmail’s search function rocks. I can search on a specific error message and pull up the current and past discussions. Same goes for the email list we use for tech support. I once had an end user that had run into serious issues and I needed help from the others who also did tech support. I was able to see everything I had done to help this person and everything others had suggested with two mouse clicks (one to select the conversation and one to expand it).

Pop access and forwarding for gmail are wonderful as well. The emails for my blogs forward to my main gmail account and are automatically archived. All of my email gets archived off line with Thunderbird.

Ads don’t bother me. I never see them thanks to Ad Block Plus and NoScript for Firefox.

All in all, my ranking is gmail, Yahoo, Hotmail.

Ralph says: May 12th, 2007 12:03pm

It’s a good thing that gmail Does have a spam filter! I have two gmail accounts. One, at some point I must have given up my address to the wrong person/web, because I get over 150 spam messages a day to that account. Gmail does catch 99.999% of them. The second account gets none, but then I rarely use it and don’t give it out. I have a Yahoo account too, that I’ve had for years. I get about 1 spam message a day on it. I use the Yahoo account.

Glen says: May 12th, 2007 12:49pm

Gmail. That application is the hub of my online business. I do need more space however!

Dave Zatz says: May 12th, 2007 4:24pm

“Unlike Yahoo! or Hotmail, you can access Gmail from a simple HTML interface inside any mobile browser ”

I can’t speak to Hotmail, but Yahoo mail has two WAP web pages to choose from when using a mobile browser. Though I pay the $20/yr which is a great value in blocking spam, dropping ads from the interface and email signature, plus allowing POP access (from my mobile). Yahoo also had push mail capabilities on the Blackberry without requiring the $20 plan. Additionally, they offer Yahoo Go (and Go 2.0) - an application for many mobile devices that includes email (without requiring the annual fee). So on the mobile side, I think Yahoo compares very favorably to Gmail.

hc says: May 12th, 2007 11:49pm

I have just loaded the Gmail client on my mobile phone, and it’s amazing. It’s fast, and read word attachments. two clicks on my mobile and I am reading email - login info stored inside the app. It’s very very good for emails that i don’t want to use my Blackberry on.

hc

The New Basement Tapes » Gmail, Hotmail and Yahoo! Mail « says: May 13th, 2007 4:52am

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Nur mein Standpunkt » links for 2007-05-13 says: May 13th, 2007 8:32am

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Dexter Zaf says: May 13th, 2007 1:08pm

I’ve been using all three for years now and I definitely prefer Gmail easily.

1. Hotmail.
Better for managing my msn contacts, in MSN Messenger. i don’t use Yahoo messenger and gmail chat cause my friends use MSN Messenger.

2. Yahoo Mail.
Best for viewing email and sending personal email. I preffer yahoo mail because it’s spam filter is great. I don’t send or read mail in hotmail because it’s not web 2.0 compliant and it’s slower than yahoo mail.

3. Gmail.
This is the best for work. I send lots of code in attachments, lots of programs, and lot’s of pictures in gmail. I don’t like hotmail because you can’t see images in small size as yahoo does, or even you can’t preview a pdf file in html and gmail does. I would use yahoo mail but gmail gives more space.

Edgar says: May 13th, 2007 10:13pm

I have 2 Windows Live Accounts, 1 Yahoo!, 2 GMAIL.

WL: This is my first choice. I’ve been using Hotmail for years and it has never let me down. Spam filtering is great and the interface is nice and smooth looking. I’m one of those people that enjoy having a nice visual to look at, something that Yahoo! can barely provide do due to all the ads, and Google is just really bare.

Google: Amazing, simply amaizing. I think I’m the only one that complains about the bare look of it and the annoying Google Ads on the right. Yes I do notice them. But it really is a great client because of all the functionality it has. Not to mention Google is one of the best companies that exist. I’m a big Google fan.

Yahoo: THE SPAM KING. I use this EMAIL as my junk MAIL give away. Each time I need to sign up for something, but I really don’t want to give away my real EMAIL, I use this. It gets so loaded with SPAM anyway, I just log in here just to erase it all about once a month.

Hands down Google is the best EMAIL client, but I really like the Visual style of Windows Live. Plus I get to have free Domains by using Windows Office Live as well. It’s a big plus for those that are looking to have personal looking EMAILs without having to spend a nickel on Domain registering.

Jeff says: May 14th, 2007 4:42am

I use Yahoo exclusively (the old version..not the new beta version). Anyway, archive SEARCH has been broken since April 1- it almost feels like the perpetual April Fools Joke that won’t end. All emails before 4/1 are searchable; everything after that can’t be found without going through the archives manually.

Yahoo used to have a link on the top of the email search results page that said “Like our New search, tell us what you think”. I complained about every other day to this problem. Now, that link is removed. Yahoo is in trouble.

Tim says: May 14th, 2007 7:23am

Personally, I switched over from Hotmail to Gmail a few months ago - the support for Live Mail in Firefox wasn’t anything that impressed me. It continually bugged out (and perhaps it was a beta version), and whenever I replied to emails it would take out all the line breaks.

Gmail is awesome - loads quick, easy to archive/sort files, and best of all I can access it from my Treo on the road. It’s simple, and also the chat integrating is great to have.

As a note to nomadicalloy - if you want to access gmail from work, chances are you want to use https://www.gmail.com. It’s probably a good idea in general, even if you’re not blocked, because it secures your transmissions.

Drainedge Link Tank · Today’s Links says: May 14th, 2007 7:41am

[...] Web Worker Head to Head (to Head): Gmail, Hotmail and Yahoo! Mail - Web Worker Daily [...]

Marc says: May 14th, 2007 9:55am

When will G mail have better accessibility to people using screenn reading software?

Web Worker Daily » Blog Archive Live.com for the Rest of Us « says: May 31st, 2007 2:11pm

[...] care what browser or operating system you’re using. For more on the new Live mail web client, read our shootout comparing it to Google and [...]

singh says: September 24th, 2007 3:52am

Is there gmail messanger that i can use to chat with all my hotmail and yahoo friends. I know yahoo have option to add hotmail friends for instant messaging.

silvia says: July 5th, 2008 9:59pm

Gmail is sooo awesome + its soooo totaly
awesome!!!!!!!!!!

silvia says: July 5th, 2008 10:00pm

gmail is the best because its verry useful!!!!!

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