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The team behind Microsoft’s oft-maligned email service, Hotmail, is hoping to score back some of its users from the titans in the industry like Gmail by doing something Google hasn’t quite pulled off: showing they are human.

Hotmail team members appealed to the community of news aggregation site by posting an “ask-me-anything” thread today, where users can come in and basically ask questions about the service and get feedback from the Hotmail team.

But leave it to the tech- and Internet-savvy Reddit community to ask the hardest question. The top-rated question in the thread is why users should abandon their Gmail accounts and head over to Hotmail. The comments immediately put the Hotmail on the defensive, with Reddit users wondering why the service didn’t use some of the most popular email protocols that sync up to mobile devices and external email programs.

Hotmail has faded into a bit of obscurity after Gmail emerged as the clear email service to beat. (Though in terms of total users, research firm comScore shows that Hotmail’s still king, with 361.7 million users compared to Gmail’s 193.3 million.) Gmail syncs with the rest of its applications like Google Calendar. Google also has the edge in that a lot of companies use its email service and connect it with other apps, like Analytics. Google Apps has signed up 3 million companies with more than 30 million users total.

The Hotmail team said Microsoft is trying a number of things to differentiate itself from Gmail and make it more viable, like removing limits on attachment sizes and offering a deeper level of connectivity with its web-based Office applications. But file-sharing is really a non-issue at this point with the emergence of services like Dropbox. Google has also been in the web-based office game for some time now.

It’s not the first time Microsoft has ventured into Reddit. The company dove into Reddit back in September to help promote the newest version of its Internet-browsing application, Internet Explorer 9. The feedback then was pretty positive — but that’s mostly because it was actually a decent application. Microsoft even purchased advertising for IE9 on Reddit, a community that hasn’t traditionally been friendly to the black sheep of the browser family.

It seems the fangs are out in this thread as well. Best of luck to Microsoft while it navigates the Internets on this one.

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