This article was published on December 10, 2010

Microsoft tries to woo Gmail users to Hotmail on Reddit, politely eats crow

Microsoft tries to woo Gmail users to Hotmail on Reddit, politely eats crow
Alex Wilhelm
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Alex Wilhelm

Alex Wilhelm is a San Francisco-based writer. You can find Alex on Twitter, and on Facebook. You can reach Alex via email at [email protected] Alex Wilhelm is a San Francisco-based writer. You can find Alex on Twitter, and on Facebook. You can reach Alex via email at [email protected]

On the very popular social portal called Reddit, companies on the occasion take the time to sit down with the community and discuss their product in the ‘AMA’ format, AMA standing for ‘ask me anything.’ Think of it as a no holds barred town hall where everyone speaks at once.

The Hotmail team took to Reddit today asking for input from current, old, ex, long-time, and new Hotmail users about what they like about Hotmail, and what they would change. If you don’t know, and we have been covering it over the last few months, Hotmail has been rapidly updating itself to catch up with Gmail in terms of capabilities and ease of use. That said, the AMA was decidedly unpleasant, with rather sharp comments coming in by the hundred; Hotmail is not popular on Reddit.

To be plain, Hotmail seems to have near zero mind share among Reddit users, a group that is generally young, male, and technologically capable. What it does have in quantity is negative nostalgia, something that the AMA stirred up by the bucket.

Before we jump into this, don’t forget that Hotmail is still much larger than Gmail. I am going to break down the big discussions, saving you the time of finding them for yourself. We did not edit the text of anything from Reddit, so there are some (sics) to go around. Let’s go:

Everyone Wants IMAP – The Answer Is No

Perhaps the most contentious discussion was around IMAP, and Hotmail’s lack of support for it. It all started like this:

The lack of IMAP support flew like a lead balloon, with user NNY76 summarizing the unhappy theme:  “Absolutely. Unacceptable. Why is there no IMAP for all Hotmail users? Why only push EAS which is a Microsoft protocol?”

The Hotmail team took the time to address all the IMPA complaints by editing their original post (OP) to better explain their position on the matter:

Really quickly, want to address the IMAP questions that have come up.We haven’t implemented imap since based on the user feedback and usage data, there isn’t a large enough need when you look at the other protocols we provide. for mobile – we believe activesync is the best story. it gives you mail, calendar, and contacts. there is big adoption of the protocol here with android, iphone, and windows mobile. for clients – with the outlook connector, windows live mail client, and pop3, we cover the majority of client scenarios. there are definitely some gaps, but not enough to outweigh the cost. one of the tough trade offs we make. let me know if that doesn’t answer the question. -ryan

Is that enough? Why not just implement IMAP and be done with the controversy? Whatever the argument, the Hotmail team seems to feel certain in their path forward.


The Hotmail team was raked over the coals about spam numerous time in the discussion, but stuck up for themselves saying that they had worked very hard to improve the spam filtering capabilities of Hotmail. In fact, they claim to have reached parity with market averages:

Lots of questions about spam too.we had gaps with spam and have come a long way in improving the spam filtering. in 2006 35% of email in hotmail inboxes was spam, today its 4% (same as best). we keep working on this ([1] hope you see a difference.2) we think a lot about design. [2] we want it to be efficient.In addition to the spam filtering effectiveness of the service, the amount of spam a particular account receives also depends on the age of the account, the account usage and other factors associated specifically with the user.

In other words: back when you used Hotmail our spam filtering was terrible, now we are on par with the best in the market, and we want credit for it.


To quickly bring you the important points that were raised we are going to have to do some more extensive quoting. We want to bring you the most important elements of what Hotmail is doing, but in their own words to prevent us from unfairly filtering their voice.

User neozz1 asked a very important question: “I switched to GMail, why should I ever switch back?” That was the real point of the AMA for many Redditors, why should I come back to the Hotmail fold? According to Team Redmond:

what’s most important to you about your email? We had some gaps on the basics, but did a ton of work to close them around spam (can give details, mileage varies by terrain), speed, storage, etc. Then, we think what are the reasons someone would want to use HM or any service?… who is it great for? For example, if you like to share photos/files with specific people (benefit of email) we got rid of pesky attachment limits. You can send up to 10GB (200 files, 50MB each) in one email via SkyDrive. If you use Office docs, Hotmail connects with Office Web Apps so you get full fidelity view/edit. If you make changes to a doc someone sent you as an attachment, and want to quickly send back those changes over email, its super easy, part of the flow. No need to download to your computer. So specific things that people do — our goal is to make them work really well.

PS – if you wanto to come try Hotmail with your Gmail, you can fully use Hotmail with your Gmail address. [1]

But that was only part of the feature discussion. Later on that thread develdevil listed out his favorite points of Gmail: “speed, interface, gchat/aim, docs/calendar integration, labs, threading, iphone works well with mail and calendar, no spam, [and] unintrusive ads.” The Hotmail crew took that in stride, and pointed out that the new Hotmail could do much of that:

nice list. I think you’ll find a bunch of stuff to like with the new Hotmail. For example, Hotmail has Messenger built-in which can connect to the largest IM networks – Yahoo / Facebook. Also we’ve integrated with the Office Web Apps for viewing and editing Office docs online without changing formatting. Plus with ActiveSync support, we can fully sync mail/cal/contacts with iPhone and most modern smartphones.
“unintrusive ads”… We are always looking to improve the quality of our ads. Some people like text ads and some people like graphical ads.. There are certain trade offs between the two – in particular scanning email contents.

My Take

I took the time to head back to Hotmail where I thought that I had started to import my Gmail account. I was going to play around in the inbox for a an hour or so to get my feet wet. My import had disappeared, so I set it up again. It didn’t work. So I did it a third time, and it seemed to catch. I confirmed my Gmail address as my own, and waited for my email to transfer.

Several hours later it has loaded 30 emails that are from October 2009. Not sure what to make of that. If Gmail in Hotmail is supposed to be their weapon to get me back, it is not sharp enough to wound, at least yet.

It was very good of the Hotmail team to show up on Reddit today and get real feedback from real people to help them improve their product. More companies should do the same thing. What comes next? Expect Hotmail to take the community response to heart and improve their email system. Will it catch Gmail? That is up to them.

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