Tuesday 25 December 2007

How to use Hotmail with Apple Mail

Update: If you're using HTTPMail with Leopard 10.5.6 - You'll have to upgrade to HTTPMail 1.53 for it to work! Click here to download HTTPMail 1.53. No wonder, my hotmail stopped working on Apple Mail after I upgraded to 10.5.6 =( ... But its all fixed now... =)

I absolutely love Apple Mail because of its simplicity and to an extent it's robustness (the To-Dos and Notes) and use it all the time when possible. I find that Entourage is a bit too bloated, and the same goes for Thunderbird. Plus, other applications don't have iCal integration, which is another application I have come to love. However, one big problem is that by default Apple Mail does not support Http accounts, so it's impossible to use mail if you use Hotmail or MSN (now apparently called Windows Live Mail). The solution was created by Daniel Parnell fit the bill. It's called HTTPMail. You can find it over at the Automagic Software downloads page.

Once you download and install the plugin, you should be good to go. Simple enough? Not really, it's Microsoft stuff, and as I've come to find out, Microsoft stuff isn't exactly simple. Yet. When I tried to send an e-mail through my Hotmail account in Leopard, I got an " *** -[NSURL initWithString:relativeToURL:]: nil string parameter" error. But, using Microsoft software for so long has taught me something - never give up. So I set out to find a solution, and finally after a couple of minutes of thinking I figured, it must be the URL, since the error had URL in it. Turns out, that you need to use some other URL to send the mail. The steps I took to solve the problem were as follows:

How to stop *** -[NSURL initWithString:relativeToURL:]: nil string parameter error

  1. Open Mail
  2. Click on Mail (in the menubar) > Preferences. Alternatively, you can press Cmd + , to open the preferences dialog
  3. Click on Accounts and select your Hotmail Account
  4. Where it says Outgoing Mail Server (SMTP) click on the drop down menu. Then click Edit Server List...
  5. Create a new entry as shown in the picture below. Make sure to use the server name oe.msn.msnmail.hotmail.com
  1. Switch to the Advanced tab for a sec and make sure it says port 25
  2. Then Click on OK
  3. I recommend you check the box that says Use only this server under the Outgoing Mail Server drop down Box
  4. Close the preferences dialog box. If you asks you if you want to save your settings, make sure you say save
  5. Send your Mail (I'm guessing you already have mail in your outbox, or else you wouldn't know about the error) through the Hotmail (or whatever description you put in) server you just created.
Hopefully, you'll now be able to send your e-mails through Apple Mail. Now you'll be able to send and receive e-mails through your Hotmail account without having to use the inelegant web-mail interface.

Got a question, tip or comment? Send them to beyondteck+question@gmail.com and we'll try to answer it in a blog post!


  1. This only works if you use the subscription hotmail account, not the free one. Unless you have another way around this glitch, it gives an error message requesting subscription

  2. No, this works for all hotmail accounts, because I am using it right now on a free account.

    I think you might have to switch to the new Windows Live Hotmail though (if you're still using the old Hotmail) in order to get the service though. Once you do that it should work with your hotmail account.

  3. you are my hero. i called the apple help hotline and they had no clue how to help me. thank's so much

  4. Thanks for the tutorial, but mine isnt working.... it says "connection to the server "oe.msn.msnmail.hotmail.com" on port 25 timed out." when i try to send messages... i know that my internet connection is working so im very confused. please help! thankyoou

  5. @ Anonymous - It seems that your ISP is blocking port 25. Some internet providers do that in order to stop people from sending out unsolicited (spam) e-mails. Try connecting with port 587 instead and see if that works.

    Hope this helps.

  6. Thanks but im still having the same problem, even with port 587.Im Still not sure what the problem is..... Hope you can help!

  7. @ Anonymous - Are you sure you are using the new Windows Live Hotmail, and not the old homail? If you're still using the old Hotmail then you might have to switch to Windows Live Hotmail in order to get pop access.

    You can sign in at http://mail.live.com I think and then start using Windows Live Mail.

  8. My account is actually a MSN account, not a hotmail account does that make any difference?

  9. Well, as long as it says 'Windows Live Hotmail' when you log in to your account online, you should be all set. If you're still having problems then try reinstalling the plugin and entering the settings again.

    Oh and are you on Leopard or on Tiger? I'm on Leopard, so I guess the settings might be different for Tiger, although I doubt the server settings are different.

  10. I am running on Leopard but i think the problem has to do with my msn account. You see, when i log in to it takes me to an older "msn hotmail" screen instead of the newer "windows live hotmail" screen. I think this just has to do with how old my email adress is...

  11. What are you talking about? You advice isn't right, because my computer (Power Mac G5 which also has leopard installed) cannot connect to the mail server "mail.live.com" or connect to the SMTP "oe.msn.msnmail.hotmail.com". I'm sure you are meant to use Exchange?

  12. Nope, I'm still using a totally free hotmail account. By the way, I was thinking about this, have any of you tried to use the Windows Live Mail application (for Windows only though) before with your hotmail accounts? Perhaps it activates some kind of a hidden feature that enables the use of http mail on an account. From what I remember I did use Windows Live Mail at one point for both the hotmail e-mail accounts I'm using in Apple Mail.

  13. Hi Rishi,

    This is a very interesting post but I still get some problem to set the plugin up. I have logged my hotmail account to http://mail.live.com to proof my hotmail account has been upgraded to Windows Hotmail Live, but still no luck. Got the message to ask me to subscription. Hopefully you could help me out, cheers

  14. Question? How do I set up the hotmail account in mail? I can not set it up so I can not click on that account to make the chamges. Thanks

  15. Hi Jessie,

    Here's a great video that might help you set up your hotmail account in Apple Mail


    However, once you install the extension, when you select the 'Account Type' you'll be given the option to choose a HTTPHotmail account, which you can use to set up your hotmail account.

    Hope this helps!

  16. Hi Peng,

    Try downloading Windows Live Mail Desktop on windows, and logging in through that. Then try logging in through the Apple Mail plugin.

    May be it might work that way. I'm pretty sure Microsoft probably has some way of stopping people from using other e-mail clients, because the amount of ads they show in their desktop and online client is ridiculous but certainly lucrative. There might be some mechanism that 'activates' something in an account to allow people to log in through desktop clients.

    So for now all I know is that I for one did try out the windows live mail desktop client, and I also used Outlook on a PC before I switched to the Mac full time.

    Let me know if this works of if this helped.

  17. Hey,

    I just followed the steps in the Read Me file and it told me exactly what to do and my hotmail works fine.

  18. @Anonymous! Lucky you, I wish if that were the case for my other account... It seems like Microsoft decides who gets to use the e-mail account with Apple Mail, and who doesn't. Because I have 2 account - on works perfectly fine, and the other doesn't work at all. Weird.

  19. i am able to send mails using hotmail through apple mail but unable to view my inbox and received mails. Please advise...

  20. it says "Could not connect to 'Hotmail Account'
    Access to Hotmail via Outlook and Outlook Express now requires a subscription. Please sign up at http://join.msn.com/general/Email"
    what should i do?

  21. @DeejayGerald: Interesting, if you can see your e-mails that you should also be able to send e-mails. Did you make sure that the port is 25, and the url is the same as listed above in the article?

    @Anonymous: It seems like you're using WINDOWS (or Microsoft's servers might now be thinking that Apple Mail is Outlook?)?!? If you're using windows then don't worry about Outlook or Outlook express, just get Windows Live Mail Desktop (jttp://get.live.com I think) and you can use that.

  22. Ok guys, another update - If you're running Leopard 10.5.6 - you'll have to update to HTTPmail 1.53 which can be found at http://www.macupdate.com/info.php/id/10842/httpmail-plugin

    Now you should also be able to donwload mails on leopard instead of just being able to send them =)

  23. @Anonymous, I'm having the exact same problem. Just got 10.5.6, and the appropriate plug-in and no dice. I don't have outlook, but something thinks I do. My hotmail account is all up to date and I've had it for nearly six years. Anyone been able to find a solution?

  24. According to http://sourceforge.net/forum/forum.php?forum_id=818174, this protocol will no longer work so we are hosed unless someone figured out a work around or wrote a DeltaSync client...

  25. HI where is the bit that says port 25
    i cant find it and mine isn't working properly

  26. I'm on windows live and I followed your instructions for trying to fix the error message "*** -[NSURL initWithString:relativeToURL:]: nil string parameter" but I still cannot send emails. What can I do next?

  27. Thanks for the tip, it works perfectly for me - I'm using a subscription based hotmail account.

    I believe this kind of access for free accounts is restricted by Microsoft unless you've ever accessed the account via their old POP3 email servers.

  28. Awesome--

    I didn't need this but I just purchased an iMac for my brother in PHX and decided to set him up in apple mail (he uses hotmail) . Worked like a charm even though I had to walk him through it over the phone.

    Just a heads up--the installer couldn't install on my personal setup--I had to manually move the httpmail plugin to the ApplicationPlugins Folder--then it worked. I believe this had something to do w/the installer not knowing how to prompt me to authenticate in order to install something into that protected folder.


  29. helppp,
    i'm new at mac, and i tried to sync my hotmail account after doing everything said above and this msg appeared.. what does it mean?

    Read error: blu111.oe.hotmail.com - Socket timeout

  30. Hi,
    I came across this blog and I hope you can help me. I have apple mail and I have run out of space on my computer to store any more mail so I have decided that I would like to set up a Windows Live Account and put all of my apple mail in there and begin to work from the Windows Live instead of the apple mail on my computer. Can you tell me how I can go about putting all of my mailboxes into windows live and how it is I can begin to send and receive emails from my new Windows Live using my apple mail email address? Many Thanks, Fer - fitness.adminmf@googlemail.com

  31. I just set up my hotmail account with the httpmail version 1.53. I can send mail and it works just fine - but I can't receive mail. It doesn't say any errors or anything - just blank. I've tried finding this "port 25" thing, but I don't know where it is.

    Please help.

  32. This plugin will not work anymore unfortunately :-(
    read below for more info:

  33. super-caler-frieken-awesome!! I just entered the servers given in the address i gave above for POP mail.. and IT WORKS! :-)
    and I don't have a hotmail plus account.. just the free standard windows live @hotmail.com account :-)

  34. POP3 access to free Hotmail accounts with Apple Mail works as of Feb 2009. http://db.tidbits.com/article/10063

  35. Hei,
    im still having the same problem.....My MAC post the following message:

    " There may be a problem with the mail server or network. Check the settings for account “hotmail account” or try again.

    The server error encountered was: The connection to the server “pop3.live.com” on port 25 timed out.""

    Does anyone know how to fix it??

  36. hi! regards from mexico, this absolutely works!

  37. wow awesome tutorial. It worked immediately. Thanks much!

    Hotmail Support

  38. I’m impressed, I need to say. Actually hardly ever do I encounter a blog that’s each educative and entertaining, and let me tell you, you may have hit the nail on the head. Your thought is excellent; the issue is one thing that not sufficient people are talking intelligently about. I’m very pleased that I stumbled across this in my seek for one thing relating to this.

    Vastu Shastra
    marriage astrology

  39. Nice blog, thanks for posting this useful information. I really would appreciate for your hard work for writing this five star post. I have bookmarked this article id for future browsing purpose.Thanks for providing such valuable tips and tricks to solve hotmail related problems, Now we can solve Hotmail or any webmail related problems (If any ) with the help of customer care services. Now we can get the details of various customer care contact numbers, tech support numbers, chat numbers, email id's from the website http://customercaresupportnumber.com

  40. Hey,

    I really learn a lot through this 5 star post! Great Job! Thanks for sharing the information. keep it up..

    Visit also:- Hotmail Technical Support

    Candy Walker

  41. Thanks for sharing helpful information . i think it's very useful for us. good job keep it up.. Windows live mail help also Call +1-800-231-4635 (Toll Free) now for Windows live mail help & Support from Microsoft certified technicians.

  42. Your blog have allot of detail about the Send video email it's good job.
    Send video email


  43. Hi, I want to express my gratitude to you for sharing this fascinating information. It's amazing that we now have the ability to share our thoughts. Share such information with us through blogs and internet services.
    Visit site