Switching to Hotmail: what’s stopping you?

Jan 26, 2012 7:23 pm by | 30 comments

ms-hotmail-logoToday we reported on an effort by our pals over at Hotmail to make a little hay on some of Google’s recent negative publicity, by posting 3 simple steps on how to switch from Gmail to Hotmail.  Since then, in the comments here and on the Inside Windows Live blog post have pointed out a number of reasons why some users may not be quite ready to make the switch (back) to Hotmail, and we thought they were worth pointing out.

IMAP/EAS
Hotmail does not support IMAP, which Wikipedia calls “one of the two most prevalent Internet standard protocols for e-mail retrieval” (the other being POP3, which Hotmail does support, but is far less functional), and that can be a problem if you’re trying to get your email onto your phone, or into a desktop email client.  What Hotmail does support is Exchange ActiveSync (version 2.5), which can be used on an iPhone or Android Phone to sync push email, calendar, and contacts.

Hotmail is supported by Apple iOS5 devices, and there are apps, for Android and even a newly released one for the Kindle Fire, so it’s getting easier to get Hotmail whatever you use, but still, IMAP is a standard protocol while Exchange ActiveSync is a proprietary, licensed Microsoft product, one that is supported by Gmail and not Hotmail, and a reason some don’t make the switch.

Calendar
A couple of commenters on the Inside Windows Live post mentioned Google Calendar as superior to Hotmail (was Windows Live) Calendar.  First, ControlZ said:

The only way Gmail currently beats Hotmail now is with the Calendar, and maybe Contacts as well. Calendar really needs search and a cleaner interface… A bit like Google Calendar. And Contacts again needs a cleaner interface, with the option to, for example, add more email fields.

I love the changes being made to Hotmail, but contacts and especially calendar need an update.

and Tomasz Olędzki added:

Reason #2 – lack of Hotmail Calendar sync in many PC/MAC desktop calendar apps (Gmail uses CalDav)

On our post as well, calendar quality was a big complaint:

From Matthiew Nate:
I am satisfied with the change regarding emails but disappointed by the calendar experience.

From doctorwhofan98:
I am also not happy with the hotmail calendar experience. It really needs search, and a cleaner interface. I personally prefer Hotmail’s interface to Gmails.

and from “0110110101100100”
calendar and contacts management. They suck. Really.

Ads
Hotmail’s somewhat glaring display ads were also mentioned, both here and on the Inside Windows Live post, in opposition to Gmail’s somewhat less obtrusive text based ads.  Back in June, SkyDrive removed a skyscraper ad to make more room for a cleaner interface, as we noted at the time:

One interesting side note – Anand Babu told us that a decision was made to take back the real estate from the former right side skyscraper ad, they simply needed more room. So instead of an ad, SkyDrive visitors will see a contextual menu

Maybe Hotmail will come to the same conclusion!

The Brand
Ok, elephant in the room time.  Hotmail just has a negative connotation in many places and among many people around the world.  In fact, back in February 2007, Microsoft attempted to change the name of Hotmail (to Windows Live Mail), but quickly rethought their “strategy”, as outlined in a Hotmail team blog post at the time:

We also found that many users were extremely loyal to the Hotmail brand and perceived the beta as an upgrade to Hotmail. In fact, our most loyal users have been very happy with Hotmail for years and while they loved the improvements in the beta, some were a bit confused by name change.
As we prepare to launch the final version of our new web mail service, we recognize the importance of ensuring that our 260+ million existing customers come over to the new service smoothly and without confusion. By adopting the name “Windows Live Hotmail”, we believe we’re bringing together the best of both worlds – new and old. We’re able to offer the great new technology that Windows Live has to offer while also bringing the emotional connection many existing and loyal users have with Hotmail.

So while negative connotations for Hotmail persist, Microsoft may be less than willing to change the name of a service that’s used by hundreds of millions of people around the world.  We do have a suggestion, however (but don’t even get us started on the missed opportunity with the @live.com domain!) – why not make better use of the custom domains features of Windows Live Admin Center?  We’re sure that many people aren’t even aware that you can use your own domain name connected to a Hotmail account (our @liveside.net addresses do exactly that), but it would seem to be a solution for those who want the convenience of Hotmail but can’t quite stomach the Hotmail name.

One positive note: Microsoft has come full circle on the importance of continuing to improve Hotmail, and we’re hopeful that these deficiencies are already being addressed.  What will it take to get you to switch to Hotmail?

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  • tk

    I use Google calendar as well as the Hotmail calendars, for different reasons.  Google is for my financial info, and Hotmail personal.  It’s great because I don’t get stuck in one platform that way.

    But branding i by far the biggest issue here.  The name just makes me cringe, it’s that horrible!  If they don’t rebrand with Skype, they are missing an incredible opportunity.

    Microsoft is on a roll now in terms of the quality of their products.  WP7 is amazing, Win8 looks so promising, and they now have Skype.  I really hope they don’t screw this up.

  • Anonymous

    Kip, Good on you for pointing out Admin Centre – I use it for 2 different domains and its kept me from moving to Office365 – maybe that’s why they don’t publicise it or update it (its still got an old header if you look -
    https://domains.live.com/ ).

    JT

  • MissRed

    Someone pointed this out some months ago….Skype..Skydrive…Skymail. Yes, Hotmail is just not an address i would want to give out.

    I can’t live without Gmails archiving either and generally better (although far from perfect) UI.

  • Damaster – LiveSide.net

    Nice post Kip! Just an update, Dharmesh Mehta responded over at the Inside Windows Live blog:
    “Definitely hear your feedback on contacts/calendar and especially ads. All things we’re looking at.”

  • Anonymous

    ok lets make a worldwide strike to change brandname of hotmail haha, , “Skymail, Skydrive, Skype” sounds good to me :)

  • Matze-d
  • Matze-d
  • markiz

    A few lines in hosts file remove the ads thankfully.

  • Anonymous

    What stops me is no “Send-As” support. I use a mail forwarding service and hand that email address out. I expect my mail provider to allow me to send email out as that address on the From line with no qualifications (Like “Send-on-Behalf-of”) so that mail continues to go through the mail forwarder. If you can’t handle that simple feature like Google, Fastmail, and hundreds of other email providers why should I consider you as an email provider and support your service?

    • Anonymous

      Maybe I didn’t get your point correctly, but I do send e.g. gmail emails from my hotmail account, and they doesn’t seem to have any particular qualifications.

  • Anonymous

    Just curious whether the issue of security is of any concern to users here.  Yes, I know it is in general, but I mean whether you’re satisfied with the level of security in place now.  Some responses at the WindowsTeamBlog to their recent post pointed out some things like:
    - lack of two-step verification like Gmail has (to keep hackers from getting in to begin with)
    - a shorter maximum password length (Hotmail: 16; Gmail: 60?)
    - special characters disallowed in the security answer

    For me, I have a very long passcode for my Gmail (I use LastPass) and a very long gobbledegook answer for the security question.  But it doesn’t feel like it’s quite as secure + safe as Gmail in that regard.  And with Gmail’s 2-step verification, Google seems to be doing more to prevent account break-ins, instead of just hoping compromised accounts can be quickly and easily recovered (as Hotmail optimistically does).

    I’d LOVE to feel as safe with Hotmail as I do with Gmail (and some of my other providers).  Do YOU all feel that Hotmail’s security measures are adequate at this time compared to Gmail’s?

    Thanks for any input!

    YoP

  • Anonymous

    The ads and it’s visually boring.  I think the brand could grasp on to some nostalgia if they simply make it more exciting to use.

    Make it pretty, simple, and functional. Get some flashy stuff in there for the tech press to take notice and people will start coming back.

    (and kill that big dumb ad on the side of the screen…. it’s awful and makes a vertical viewing pane completely useless.)

  • Sascenter

    A little metro refresh would be great, mostly because Calendar and Contacts really need an update in my opinion.

    It’s crazy that I can’t have a normal address book because there are different contact info fields on Hotmail, Windows Live Mail, and my Windows Phone 7 device.

  • Anonymous

    Damn it! I Love Hotmail and leave the name alone.  If you want Gmail, go to Google.  If you want Yahoo mail, go to Yahoo.  If you want AOL mail, go to AOL. All of these email providers have something different and unique that distinguishes them from each other. I have tried Gmail and it has some nice features. However, it boring as hell design wise and sucks when it comes to not being able to pay for an account without ads. I love Hotmail’s interface.  I also love the features that Hotmail offers, and the fact that you can pay for a premium account with no ads. I do agree that the Calendar part needs a major makeover with newer features and icons for appointment representation.  The contact list in Hotmail needs changes too. The contact list should allow us to upload peoples pictures in the icon box, not rely on Windows Live Profile.  There are a lot of empty picture icons in my contact list because people are with different services and not Windows Live Profile. It should not be tied down to just people have to joining Windows Live Profile or Facebook to get a picture in that empty avatar box. I should be able to upload my own personal picture of a friend or family member in that avatar box and it should be able to go across the whole Windows Live platform. When you click on a contact in your Windows Live Hotmail account, not only should you be able to see a contact’s information, but a summary from services like Facebook, Twitter, Calendar (Meeting request). For example, there is a lot of empty space in a contacts profile. To the right a summary could be created showing Facebook status, a meeting request that you have with that contact that you invited on Windows Live calendar, photo uploads to third party applications. It would be just like Messenger social on your profile page but only showing what is going on with that individual contact. Windows Phone 7 already does this, why can’t contacts in Hotmail do the same thing without being just stuck to Windows Live Profile.

    • http://doctorwhofan98.wordpress.com/ doctorwhofan98

      That’s exactly what I think. I also like the Hotmail interface (and name), and agree that calendar needs an update. It’s definitley annoying not being able to choose a picture for someone in your contact list.

    • Sascenter

      Thank you! Exactly my thoughts.
      It should work exactly like WP7′s contacts. You see what’s linked, get information from multiple places, and be able to edit photo.
      Also, I think there should be some way to clean up a contact. Right now, I don’t know what would show up, if a contact has different (not up-to-date) information on Windows Live / Facebook. And my own Address Book modificaitons overwrite those? Or the other way around? I think it should show information for each of the accounts under one contact.

  • http://www.allchainsawparts.com/ alliegladson

    Last year I erased my hotmail account, because I didn’t want to use it anymore. Last week I wanted to know if I still can access that hotmail account, because it said it would be deleted within 60 days or so. voila! I still can access my hotmail account, what has surprised me is new emails are still coming into inbox. Now I know that I can not delete hotmail account forever!

  • Peter Henkel

    Hotmail won’t group messages into threads when they have same subject and sender, and it won’t allow me to return beck into messages list.

    • Anonymous

      Peter,

      If I understand your point correctly, you should know that Hotmail DOES have a ‘conversation’ arrangement option.  (On the right-hand side of the message list, click the drop-down arrow under “Arrange.”  The bottom selection is ‘conversations.’)

      But it’s not as good as Gmail’s, IMO.  Hotmail uses the ‘most recent message on top’ approach.  So, one reads each individual message downward, but then must scroll back upward through that message and through the next message to its beginning, then read that message downward, then scroll up again through that message one just read and through the next message to its beginning, read downward, etc.  Too much down, up, down, up, down, jerkiness for my taste, esp. when one wants to read through most/all of any given conversation.

      I much prefer the “most recent message on bottom” approach as Gmail has.  (But I really don’t use my Gmail account all that much and don’t really need the conversation view anyway.  But for me the downward conversation arrangement of Gmail (and MyOpera & FM’s new beta webmail, both of which I DO use and like) is more intuitive.

      • Peter Henkel

        Yeas, it does, but only when new mails are direct replies to the previous one. When you receive mails that are not replies, but have same sender and subject, it won’t group them into conversation. Until Hotmail incorporates this, I’m sating with Gmail.

        • Anonymous

          Ah.  Okay, I see what you’re saying.  Thanks for clarifying.  :-)

          I just tested it for myself.  I sent an email from Gmail to Hotmail and replied from Hotmail to Gmail and the two emails were grouped into a conversation.

          Then I sent an email from Hotmail to Gmail (same sender and same subject) and it was NOT grouped into the above conversation.  Gmail made it into a **separate** conversation.

          But then I composed a brand new email in Gmail and used the same subject line as the above emails and sent it off to Hotmail, and Gmail grouped *that* email into the first conversation mentioned above !   :-

          So, it seems that (in my case at least) Gmail only grouped emails into conversations when they were either 1) direct replies back and forth, or 2) a separate email **composed in Gmail** using the same subject.

          However, I also have emails in my Gmail archive with the identical subject that I sent to two different recipients (over a year ago), and Gmail did NOT group those into one conversation for some reason !

          Perhaps your experience with Gmail’s conversations is somehow different than mine.   ??

          In any case, I do know that some Gmail users complain about emails being automatically grouped into a conversation merely because they have an identical subject.  Sometimes that auto-grouping is exactly what users DON’T want to happen.  What such users want — and I think this would satisfy your email needs and other Hotmail users as well — is to be able to *move* emails in or out of a conversation manually, if one was incorrectly put in a conversation (or left out of one).  Now, the freedom to do *that* would be a feature that both Gmail and Hotmail should implement asap !   :-)

          • Peter Henkel

            “However, I also have emails in my Gmail archive with the identical
            subject that I sent to two different recipients (over a year ago), and
            Gmail did NOT group those into one conversation for some reason !”
            There is your problem. Subject AND sender/recipient has to to be the same.
            For example, when your have subscribed to forum thread, every notification email will be grouped into conversation, because subject AND sender is the same. However, in Hotmail every notification email will be shown separately.

          • Anonymous

            Ok.  Now I understand !  :-)

  • Anonymous

    I would love to entirely move from Gmail – which I use for mail archiving – to Hotmail. However, as the number of folders and subfolders is limited to about 120, I currently have no chance to do so.

  • altalff

    for my self, I have tried many times to switch but i found it useless. for a reason that the hotmail is 5gb and my email size is 6 to 7 gb and the msn team not accepting to increase my inbox size.

    so better to migrate to yahoo but trueswitch is not working with them. so the second option is the AOL.

  • Guest

    Typical MS. Do nothing to fix the product while others innovate and gain momentum. Then when the brand is severely damaged and market share eroded to the point where even MS can’t deny it’s being beaten, refocus on the product and finally do what they should have done all along – innovate, only now it will cost way more and is too late.

  • Kevin

    Here’s what keeping me from using Hotmail and why I switched to Gmail:

    -No IMAP support. Deal breaker right out of the gate. I want to ability to use my own e-mail client, not what Microsoft wants me to use.

    -Terrible UI with huge ads. Gmail’s UI is much much simplified and easy to use with minimal or no ads whatsoever.

    -If you don’t log in after a certain amount of time, all of your e-mails get deleted. It used to be after 30 days, but now it’s 270. This may of been more understandable back then when space was at a minimum, but it’s clearly unacceptable today. Gmail has never done this, and a number of people who I know lost important e-mails that were in their Hotmail accounts because they didn’t log on for 30 days. That was enough to send them packing.

    -Terrible spam filter. I can’t count how many times messages that were clearly spam made it into my inbox. Gmail’s spam filter has much better and I’ve never encountered one single spam message in my inbox ever.

    -The brand name in general. Whenever people think of Hotmail, they’ll think of those immature screen names that were made up when they were much younger. Hotmail is regarded is completely unprofessional while Gmail isn’t. I would never dream of giving a Hotmail address to a professional contact or putting it on an resume. What Microsoft should do is rebrand as @office.com and use the Outlook 2010 web interface that comes with Exchange 2010. It would look a lot more professional, maybe even more so than Gmail.

    The central issue is trust. Microsoft has done a very good job proving that Hotmail is not a trustworthy e-mail service. In order to win people back, they have to do something that would completely blow Gmail out of the water and not just play catch up. Gmail Labs is one of the best things ever and introduced features that blew other web based e-mail services completely out of the water. Until Microsoft can do something that will win people’s trust back, don’t expect them to leave Gmail for Hotmail anytime soon.

  • Anonymous

    A month ago, I commented on a Microsoft rebranding article.

    http://www.liveside.net/2011/12/08/more-info-and-some-speculation-on-the-microsoft-live-rebranding/#disqus_thread

    My comments there seem appropriate here, so, instead of rewording what I wrote, I’ll just cut and paste it here.

    Let the Microsoft research/marketing team earn their salaries and come up with a better name besides Hotmail, to something more formal/professional, a name more appropriate to be associated with Microsoft.

    With the upcoming Windows 8 and Windows Phone 8 releases, this is a great
    time for a Hotmail rebranding.

    Hopefully someone at Microsoft will read our comments and will seriously consider a change from the Hotmail name.

    Here’s what I wrote a month ago…..

    The majority of users and businesses don’t really care of Hotmail’s name history with HTML.
    Most just associate it with the word “hot”.  The definitions for “hot” in the Urban Dictionary
    are the words people think of “hot” first.

    Others associate it with Hotmail’s stigma of spam and unreliability from the past.
    As mentioned before, I’ve read and have seen people/businesses immediately ignore/reject
    emails, resumes, etc. with the Hotmail domain.

    I’ve been a strong proponent of changing the Hotmail brand. All the awesome changes/additions Microsoft is doing is wasted with the Hotmail name.

    Windows 8 (OS & phones) in 2012 is Microsoft’s chance to make a fresh start from the confusing and inappropriate naming conventions (Hotmail, Live, etc.) of the past.

    Some excellent suggestions have been made here, such as having the prefix “Sky” (SkyMail) or the “X” (XMail).  Surely Microsoft can afford to acquire those domain names.  Both can be an excellent direction, especially with the SkyDrive and XBox brand name recognitions.  Either one are better than the name Hotmail for personal or business use.

    Too bad Microsoft was beaten by Apple for the ME.COM domain for email.  That would have been awesome to have as the domain for Microsoft Email.  Or Microsoft can acquire the domains MM.COM or MSMAIL.COM, for the name Microsoft Mail.

  • http://www.contino.com/ Andrea Contino

    I really hope that someone at Microsoft is reading this. They just have the recipe for success to beat Gmail. Just follow your customers…

  • Reese Cooper

    My love/hate for Hotmail is documented here (http://myconstructedreality.wordpress.com/2011/10/09/i-love-and-hate-hotmail/) and here (http://myconstructedreality.wordpress.com/2011/10/10/continuing-my-lovehate-with-hotmail/).  My main complaints are poor integration with google calendar (my wife switched from Yahoo! to Google) and not being able to chat with google contacts (though this insn’t too much of a problem due to Facebook chat integration in Windows Live).  Also, if Microsoft would create some type of dedicated rss reader within Windows Live (like Google Reader).

    So in a nutshell, my 3 things that I need in order to 100% switch back to Hotmail are: 1. Ability to sync Windows Live Calendar with Google Calendar so that my wife and I can stay on the same page across services. 2. Windows Live needs a web based rss reader (the reader in the Windows Live Mail desktop app doesn’t count). 3. Chat integration with Gmail contacts (though this isn’t a deal breaker because 95% of my gmail contacts are also Facebook contacts).

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