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Let's be honest: For a long time, it was a little embarrassing to use a Hotmail address. I should know -- I've been using Hotmail as my primary email since I first got an account in 1999.
I wish I could say that I never looked back, but when I saw all of my friends and professional colleagues touting their Gmail addresses in the mid-2000s, I considered switching. Certainly, I created and maintained a Gmail account, but I decided all those years ago that I wanted an email that wouldn't change, so I stuck with Microsoft's Hotmail, despite its poor storage capacity and the torrents of spam.
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To anyone without that interest in email permanence, Gmail was an easy choice. Its clean layout, easy archiving and seemingly endless storage wooed many digital influencers and their followers. Although Hotmail always bragged more overall users, everybody in the know had figured out that Gmail simply outclassed Hotmail in pretty much every way that mattered.
As time went on, Microsoft added new features to Hotmail and caught up with Gmail in many respects. But the damage was done. Even after Hotmail offered nearly unlimited storage, much improved spam filtering and useful inbox-cleanup features, the stigma remained. If you saw the @hotmail.com domain in someone's reply-to field, it necessitated a tsk-tsk -- or at least a roll of the eyes. You have to wonder how many resumes were thrown in the trash at tech companies because the applicant had put a Hotmail address in their contact info. Gmail won.
Then: Boom. Last month, Microsoft changed the game, re-launching Hotmail as Outlook.com, casting aside its tarnished brand and giving the service a major makeover, along with some game-changing new features.
Is it as good as Gmail, though? Where does each service excel, or fall down? And will the switch to Outlook for web mail finally enable Microsoft to cast off the stigma of Hotmail? Let's look closer.
The absolute basic basics of the two programs -- composing messages -- is actually fairly different between the two services. Gmail opens up a clean message but retains the Gmail template, with your labels and chat contacts on the side. Outlook, on the other hand, brings you to a compose page where it's just you and your email.
The Gmail approach is more versatile. While you're writing your message, you can click away at any time and Gmail will automatically save a draft. Outlook instead simply gives you a warning that you haven't yet saved your draft if you try to leave before hitting send. That makes saving drafts a two-step process -- slightly more inconvenient.
The idea of getting shunted to a dedicated composition page has some merit. When replying to long email chains, for example, you'll inherently see more of the message on your screen.
Outlook doesn't offer as powerful editing tools as Gmail does, though. While both programs will let you compose messages in rich or plain text, Gmail has a Clear Formatting button, which I've found extremely useful whenever I need to copy-and-paste some text into an email. Outlook.com lacks this feature, although it can do something else Gmail can't: setting message priority (although I've always found it more effective to simply put "URGENT" in a subject).
Outlook, however, adds a very nice aesthetic touch to the act of sending an email. When you hit Send, the message shrinks within the window for a second, then moves upward slightly (sucked into the "tubes" of the Internet) right before the app tosses you back to your Inbox.
Google is doing its best to become a heavyweight among social networks, and it shows. Gmail is hard-wired into Google+, showing you notifications and your G+ profile pic in the top right at all times. It's always been a one-click experience to start IMing with someone via GChat, or a voice call via GTalk, on the left rail. Finally, Gmail just integrated Google+ hangouts into Gmail in lieu of the old video chats.
Still, that's about as far as it goes. Given the areas they compete in, Google has fairly icy relations with Twitter and Facebook, so you won't see them here. But Outlook.com ties into both of those services in a fairly novel way.
In Outlook, whenever you click on a message from an actual person (as opposed to a newsletter or notification) you'll see the latest updates from that person's Twitter and Facebook feeds on the side. You can even Like and retweet posts without ever leaving Outlook.com.
Sure, Gmail will show you Google+ profile information of the person you're emailing, but that's about it. Seemingly, Outlook wins here except it so far has no integrated way to start a video or voice chat with someone (regular IMing has always been integrated with Windows Live Messenger). Microsoft says Skype will fill this gap, but the feature has yet to appear.
Ads are annoying -- unless of course the ad is advertising something you actually want. To my recollection, I've never once clicked on an email ad (whether text or display), so that either says those ads do a bad job of doing that, or they're simply not noticeable enough for it to matter.
In its Outlook metamorphosis, Hotmail ditched display ads in favor of text ads along the right side. This made it more like Gmail, although there are a few differences. For one, the Outlook ads are visible even when you're just looking at your Inbox; on Gmail, they only appear when you have a message open.
More importantly, the ads disappear on Outlook when you select one of those messages from an actual person, replaced by the social-network info mentioned above. Gmail shows you ads on all messages.
The third difference is in how you actually interact with the ads. If you mouseover one on Outlook, an image appears over it. That could be of interest to advertisers, since it seems to be designed to increase engagement, although it's too early to say whether it's effective.
Finally, although few will take advantage of it, Outlook.com still offers the old Hotmail Plus service of doing away with the ads entirely for a yearly fee. You'll need to switch back to the old Hotmail to sign up, but once you do you can switch back to Outlook and never see an ad again. Gmail has no such option.
This one is really no contest. Gmail offers two-factor authentication, and Outlook.com doesn't. The word "security" doesn't even appear on Outlook's options page.
When I asked Microsoft why it didn't offer two-factor authentication for Outlook, a company spokesperson reminded me the service was technically still in preview, and that it required strong passwords and had "good server-side detection."
The rep also said Microsoft was researching security issues while in preview so it could find a "strong solution that everyone could use" as opposed to "just the 1% of users that figure out how to navigate a bunch of additional setup options." (More info in this story.)
So perhaps Outlook's security will get better in the near future, but for now, if you want a secure, free web email service, that's Gmail.
For most of Hotmail's history, superior organizing tools are what it held highest over Gmail. For anyone thrown by Gmail's use of "labels," Hotmail's more-familiar folders and its ability to rearrange your inbox (or any folder) by date, sender, subject or size with a single click were beacons of normality.
That still holds true with Outlook. Folders remain the primary way to organize your email, and it also retains Categories, which automatically classify your incoming messages as "social updates" or "newsletters," for example.
Outlook's tools aren't just there to satisfy left-brainers, however. The service also arms you with a few tools that help you keep overloaded inboxes under control. First it offers a quick way to "Sweep" up all messages from a sender or senders, deleting (or moving) each and every one of them.
It also provides an easy way to schedule cleanups -- say, deleting all notifications from Twitter or Facebook every few days, negating the need to even remember to Sweep. Although Gmail offers a Priority Inbox feature that comes in handy for putting important messages front and center, it doesn't have anything comparable to a scheduled cleanup.
Finally, there's the simple Preview Pane, a standard feature on Outlook that you have to enable through the "Labs" tab in your Gmail settings to enable. While Hotmail/Outlook has borrowed the best features from Gmail over the years -- such as free integration with mobile email clients and conversation view -- I don't understand why Gmail hasn't implemented this feature, which I view as fundamental to any email client.
And so the final score is two points per side -- a tie. While Outlook.com has a lot going for it, and it's a huge leap forward for Microsoft just in terms of brand, Gmail is still superior in some key ways (security being the biggie). But Outlook.com represents a rebirth of Microsoft's web mail service, and the company appears to be investing much more into it with the launch. Perhaps a rematch will yield different results in a few months.
In any case, the rebranding of Hotmail as Outlook.com has given users of Gmail and Yahoo Mail a reason to try something new. Even better, it's given them an email address they don't have to be embarrassed about.
Image courtesy of Adamlmhotep.
This story originally published on Mashable here.
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