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I have had an Hotmail account since 1997 (i.e. don't ask me to switch - have hundreds of filters and folders and thousands of contacts) and I recently switched to a Mac and I am looking for a Mac client that would deliver the same functionality as Windows Live Mail did in my PC. Also, don't ask me to forward/import to Gmail. I have tried that numerous times - Gmail fails at importing filter rules or nested folders properly from Hotmail and it also has numerous issues with sync and contacts etc when importing from Hotmail.

The Mail.app only supports POP3 for Hotmail which I hate because it is only local sync - I am looking for either IMAP/DeltaSync/Exchange (i.e. 2-way sync) for my Hotmail to work in Mac. I tried Postbox/Sparrow Lite/Outlook in Mac Office 2011/Thunderbird with webmail plugin/Eudora and none worked. I tried mBox for Mac and it worked great for about 2 weeks and now it stopped working with the new Lion Mail.app update. In anycase, mBox has been out of development since 2009. I looked at IzyMail but I am not willing to pay a subscription - I don't mind paying a one time fee though.

Hotmail used Exchange ActiveSync which works well on my iPhone. Mac's Mail program works with many Exchange servers, so I am really confused why Mac Mail cannot ActiveSync with my Hotmail account which apparently supports Exchange.

I just want a mail client that truly syncs with Hotmail. Information to a POP3 clients flows one way so the Mac cannot update the server with read status, reply status and more.

I am willing to pay for a solution and I just can't find such a software! I am also willing to pay a one-time fee for an IMAP gateway too and I can't find any such thing either.

Is it really that hard to get Hotmail working in Mac?

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  • 3
    Mail supports more than just POP3. (Or am I missing something implicit in that comment?)
    – mipadi
    Commented Apr 13, 2011 at 15:31
  • Yes, Mail supports POP3 but POP3 is ancient. I want a protocol that supports syncs (IMAP/Exchange)
    – pathikrit
    Commented Apr 14, 2011 at 4:06
  • 2
    @wrick: I know, but Mail also supports IMAP...
    – mipadi
    Commented Apr 14, 2011 at 4:21
  • 6
    In a word - Yes. It is difficult to get non-Microsoft clients to work with a service that MS specifically designed to work poorly with such clients. Now that you understand the phrase "vendor lock-in," you have a choice to make - switch to a service that supports vendor-neutral standards such as IMAP, or return to the vendor that's trying to hold you hostage to their proprietary non-standards.
    – Sherm Pendley
    Commented Apr 17, 2011 at 1:37
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    @koiyu - Yes, I have (tried both Exchange 2007 andExchange IMAP options in Mail.app) it does not work on Mail.app (those settings work fine for my iPhone). I have half an idea to examine what goes over the wire and let M$ think Mail.app is my iPhone.
    – pathikrit
    Commented Apr 17, 2011 at 20:58

18 Answers 18

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Pipe your hotmail through a Gmail account, either by forwarding everything from Hotmail to Gmail or by setting Gmail to download your Hotmail using POP.

Configure your Gmail to send using your Hotmail credentials.

Then access your Gmail in Mail.app via IMAP.

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    Thought about it but it does not really work as my Hotmail account has many folders and my emails get filtered into them automatically and Gmail does not do a great job of importing those folders (it only imports the inbox)
    – pathikrit
    Commented Mar 26, 2011 at 16:33
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    This is by far the best way to go. Sure, a bit of pain importing in your old folders, but it is possible. I'd setup a gmail account first and create all your rules/filters/labels. Then I'd go into your hotmail, move all your email from the folders back into your inbox and mark them all as unread. Then let gmail import them all into gmail. It will do all the filtering/labelling based on your rules. Once you've done this, configure gmail in Mail.app and your iPhone. You can even configure gmail to send email with your hotmail email address. A little pain but a lot of gain.
    – robzolkos
    Commented Apr 25, 2011 at 8:45
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    I'll +1 this as well. No one will know you are using gmail or IMAP to send/receive hotmail. You don't have to lose that account - just the restrictions in using each message with a server that doesn't sync. When most people realize that the from field still shows hotmail, replies still go to hotmail, and their messages from hotmail get tagged/organized in gmail they make the jump. I don't care if my neighbor drops my mail off at the post office - as long as it doesn't delay my mail and isn't hard to set up or understand - passing POP through IMAP is very feasable to allow true syncing.
    – bmike ♦
    Commented Apr 25, 2011 at 18:54
  • As far as I know forwarding from hotmail to gmail is not free.
    – Rabarberski
    Commented Aug 1, 2011 at 8:21
  • @Rabarberski - Forwarding to Hotmail is free as I currently have my wife's email configured in exactly this way. The thing to remember though is that you need to login into your Hotmail account once every 6 months to stop it being deactivated as an idle account.
    – David Webb
    Commented Oct 18, 2011 at 17:50
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Hotmail doesn't have IMAP/Exchange support, it has Exchange ActiveSync support, but only for mobile devices. Everything on the Mac side, even MS's own Outlook 2011, uses POP3 to connect to Hotmail.

You could file a support ticket with the Mbox folks, and hopefully they'll have a timetable for updating their product to work with the new version of Mail.app.

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  • I did submit a ticket - no response. They have not updated their software since (fluentfactory.com/mboxmail-for-mac/purchase.php) 2009
    – pathikrit
    Commented Mar 26, 2011 at 16:31
  • Is there any way I can "fake" to be a mobile device? Are there any mbox/izymail alternatives?
    – pathikrit
    Commented Mar 26, 2011 at 16:34
  • I think the community has largely given up on HotMail on Mac OS. The ways to fake being a mobile device are way too complicated to be worth the effort: install the iOS SDK, run the iPhone Simulator, and use the iPhone Mail app to check your email. I think your best bet might be to leave HotMail's web site open in a Single Site Browser, like Fluid App — it's a web browser, yeah, but you're never going to get Mail.app to talk to HotMail.
    – Dominic Mauro
    Commented Mar 27, 2011 at 1:54
  • What protocol does Windows Live Mail use? I think it uses DeltaSync. Is that hard to implement on the Mac? I believe its free to license.
    – pathikrit
    Commented Mar 27, 2011 at 19:59
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+50

The basis of your question rests on the fact that you're not willing to relinquish your hotmail account. Of course, this may be reasonable because, amongst other reasons, all of your contacts have the email address, you're comfortable with how it works, etc.

There are currently no OS X DeltaSync-based clients, however you could consider building a solution based on jdeltasync.

Given that you're willing to pay to retain your Mac and stay with Hotmail, a different solution which will let you keep your Mac yet give you access to hotmail syncing is a virtualisation product (for example VMWare, Parallels, CodeWeaver) and use an appropriate windows client. The level of integration they offer is pretty good.

Looking to the future, you may want to consider purchasing your own domain name and use it with a suitable mail service (for example, hosted Exchange) and slowly migrating your contacts to your new address. This will ultimately give you more control over your own needs instead of relying on others to provide support for a particular protocol.

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No - not even Outlook 2011 will DeltaSync with hotmail. You'll have to run a windows client in emulation or host a proxy server to translate DeltaSync to POP3/exchange/imap.

This is more a business problem and therefore a social problem than a technical problem.

I am not a lawyer - but it's likely against the terms of service to provide a paid service like you ask to truly integrate a gateway into Windows Live with ActiveSync (or DeltaSync). I recall that for a while, you could simply set up Apple Mail to point to m.hotmail.com and it would work so it's pretty clear that measures are actively taken to prevent non approved clients from speaking with hotmail using sync.

Microsoft is on the record that their live sync technology is a competitive advantage and they are only offering it presently to people that pay for either Windows or to license ActiveSync. I would expect their licensing fees they would seek to allow a non MS client to benefit from their hard work is high enough to prevent this from happening.

Numerous discussion postings are asking for and aknowledging that Outlook for Mac in Office 2011 does not sync with hotmail / windows live servers.

Hopefully this will help you decide to keep using mail that doesn't do what you want or help decide to invest the time to learning how to preserve access to hotmail but forward / send using IMAP and another service. It's not ideal since it's now two accounts to remember, set up, but it's not against the terms for now and less likely to be broken by Microsoft if they catch you forwarding your mail or accessing it from elsewhere using POP.

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    Ok, this confirms my suspicion - there are NO software out there for Mac that syncs with Hotmail. Is it that hard to build one considering it works on my iPhone just fine??
    – pathikrit
    Commented Aug 8, 2011 at 17:51
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Firstly some solutions (some named previously) -

  1. Switch to Gmail: This is your best long term solution. Mac OS X 10.6 Snow Leopard and Mac OS X 10.7 Lion properly supports Gmail/Google Calendar/Google Contacts.

  2. Use mBox Mail (with any Mac e-mail app that supports IMAP): It's been updated to support 10.6 Snow Leopard and comments above says 10.7 Lion too. It was lasted updated in August 2011. This won't sync calendar/contacts just e-mail/e-mail subfolders. It is only a one off fee of $19.99 USD.

  3. Use IzyMail (with any Mac e-mail app that supports IMAP): I believe this works in a similar way to mBox Mail, by way of a web proxy to the companies own IMAP server. This also won't sync calendar/contacts just e-mail/e-mail subfolders. The website looks dodgy to me but it is only $18 USD a year.

  4. Use Hotmail.com (or Gmail.com) and forget the idea of using a desktop client. This wouldn't suit me but it does many people.

  5. Use Windows. I know hardly a solution but Outlook 2003-2010 (after you've installed the Hotmail Connector add-on) and the free Windows Live Mail fully support Hotmail's DeltaSync. Which is ultimately what you need to get what you're after.

Even using mBox Mail/IzyMail you still won't have your Calendars and Contacts synchronised. Hotmail doesn't support CalDAV which is the universal calendar equivalent of IMAP, meaning no Mac OS X software is able to talk to Hotmail's calendar and you can forget contacts sync.

All the other options mentioned by others above look very complicated, certainly more so than switching mail accounts (assuming mBox Mail and IzyMail fail).

Migrating from Hotmail to Gmail is much easier than you think.

Others have said you can setup Gmail so you can "Send As" your old e-mail address and you can set Gmail to download all Hotmail's e-mail.

This is a pain though (especially if you've got subfolders). If you can get hold of a Windows PC temporarily there is a MUCH easier way. Open Outlook or Windows Live Mail and add Hotmail, also add Gmail using IMAP.

It's then a simple case of dragging and dropping the Inbox and Sent Items contents from one to the other, then dragging each subfolder from one to the other.

This also works when migrating from any IMAP compatible e-mail provider to another IMAP compatible e-mail provider.

Finally Google has equivalent filtering rules, you'll only need to set them up once.

I also suggest you read "Comparison with Google Sync" below.

Now to debunk some inaccuracies stated above :-) -

Hotmail supports Exchange ActiveSync for mobiles and DeltaSync for desktops. It also supports POP3 for mobiles or desktops (the only non-propitiatory format it does support).

For all those people who think Exchange support also means Exchange ActiveSync. It doesn't! EAS is an extension of Exchange, it is not Exchange!

It won't work in Outlook for Windows, Outlook for Mac or Apple Mail, all of which support Exchange but do not support EAS. If it used to work by entering the Hotmail EAS server details into an Exchange compatible client it's more by luck. It's unlikely to be Microsoft stopping you, the technology isn't designed to work that way.

You'd think they could make EAS work on desktops too but literally no desktop client has ever supported EAS (Mac or Windows), there's got to be some reason why that's the case. It could be a technical one or it could be Microsoft doesn't want you using a mobile technology on desktops. We'll never know.

Microsoft are on record as saying IMAP is an old technology and DeltaSync is much better. This is true. It's able to synchronise e-mail, contacts, calendar, tasks and I think notes. It's also much more efficient than IMAP at handling e-mail.

Microsoft's technical reasons for creating a new technology are sound but lets face it the real reason is to stay propitiatory. If you recall it used to be the case that Hotmail didn't support Exchange ActiveSync or POP3. You could only access Hotmail at hotmail.com.

Microsoft aren't going to support IMAP, it's not going to happen.

The trouble is Exchange, Exchange ActiveSync and DeltaSync are propitiatory which require a licence. Apple licensed Exchange and Exchange ActiveSync from Microsoft. There's no reason why Apple couldn't licence DeltaSync (that I know of).

I doubt they will though, to the best of my knowledge only Hotmail uses it and it's clear Apple would prefer you use MobileMe or Gmail. The blame here rests as much with Apple as Microsoft.

Exchange brings in potential big business support and EAS is the universal mobile standard for e-mail/calendar/contacts sync. DeltaSync just gives Apple Hotmail.

Comparison with Google Sync -

Google Sync supports EAS, POP3, IMAP and CalDAV. Using the latter two methods you can get proper e-mail sync and calendar sync. Outlook or Windows Live Hotmail don't support CalDAV but Apple iCal, Mozilla Thunderbird (with Lightening calendar add-on) and Mozilla Sunbird do.

To my knowledge there's no way to get contact sync except the business Google Apps.

Apple have added their own Google Sync into Mac OS X 10.6 Snow Leopard (I think 10.6 not 10.5) and further enhanced it with Mac OS X 10.8 Lion. They do this using IMAP for Gmail, CalDAV for Google Calendar and I don't know how Google Contacts works but something similar.

Microsoft haven't added zilch Google Sync support to Windows (why would they?). You can use Mozilla Thunderbird (with Lightening calendar add-on) and Mozilla Sunbird though or if you prefer using Outlook there are plenty of third party Google Sync tools.

I use GSyncit to synchronise Google Calendar/Google Contacts which works brilliantly and obviously Outlook natively supports IMAP.

The best you can expect with Google Sync and Windows Live Mail is Gmail IMAP, no Google Calendar Sync or Google Contacts Sync.

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2

Try using winebottler and wrap it over Windows Live Mail. A few winetricks may be required, but it's worth a try. If you have a windows pc, use the web installer and take the .msi file for windows live mail. Otherwise, download it from here.

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Try with mBox Mail for Mac; it will sync your Hotmail with any Mail client on a Mac. I just set it up on Outlook for Mac, and all my Hotmail folders are visible.

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On Sep 11 2013, Microsoft released full IMAP support for Outlook: http://blogs.office.com/b/microsoft-outlook/archive/2013/09/12/outlook-com-now-with-imap.aspx

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There is one supposed way to do it with FreePoPs with Mail, but unfortunately syncing the way you mentioned is not available.

If you want syncing, take the pain, move to gmail. Its better in every conceivable way. It can even send emails as your Hotmail account if you are married to the address.

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  • As I said, moving to Gmail is out of the question - I have been using this email account for 15 years now - I have hundreds of filters, thousands of contacts, hundreds of custom folders.
    – pathikrit
    Commented Aug 8, 2011 at 17:49
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Similar to the gmail solution, you could use Fastmail. I've been using this setup for the same reasons as you (main address is hotmail since 1999, OSX, want IMAP) for a few years now.

It has two advantages over gmail:

  • you can forward your hotmail to your fastmail account. (Gmail only allows periodic POPing).

    Edit (October 2011): It appears that since very recently forwarding from hotmail to any other domain is now free. So the trick below is not so relevant any more.

    The trick why this works is because if you have a fastmail account or alias (one account allows multiple alias addresses), say [email protected], you also have automatically a number of other addresses, including [email protected].
    Now, hotmail allows forwarding for free only to cetain approved microsoft domains (live.com, hotmail.com, msn.com, etc) but it only checks for the part directly after the @ ! So if you create a fastmail alias with one of the approved hotmail domain names, you can configure your hotmail to forward to [email protected]. The trick is explained in more detail in this forum thread.

  • Fastmail allows sending via an external (i.e. hotmail) SMTP server, even if you're using the fastmail SMTP server in your email client! (gmail also allows to use an external smtp server, but not when you're using an email client setup to use the gmail smtp server, I think, the gmail help article [note at the bottom] is not clear about it)
    This feature prevents a security warning from popping up with people using hotmail in a browser themselves (because otherwise hotmail thinks you are spamming because you have a hotmail 'From:' address but are sending from a non-hotmail smtp server ). For more info see this page and the linked Fastmail blog past.

Fastmail is an email provider focussed on IMAP. Not free for your purpose though (the free 'Guest' level has very limited storage). For what you want, you'll currently pay around 20$/year

All my mail is in my fastmail account, aggregated from different (hotmail and other) accounts. The day hotmail drops the forwarding trick, I'll (finally) drop my hotmail as well.

(My address book contacts is quite an involved setup as well (but worry free once done). My fastmail contacts are synced two-way with gmail, and this again syncs with the address book of OSX)

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  • Cool solution, my only problem is I want a one-time payment software and not subscription plans. Else, I will just use Izzymail.
    – pathikrit
    Commented Aug 8, 2011 at 17:47
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I was able to get Outlook 2011 and Thunderbird working with mBox with Lion OS. The issue you are having seems to be a mBox compatibility issue with the Apple Mail program. I too have sent email to mBox, but there has not been an answer yet. So I download the free trial of Office.

To setup the account, enter in your email account/password then uncheck the "Configure automatically" box. You can then change the account type to IMAP and the server to localhost:9143 (no SSL) as is required by mBox and the outgoing server smtp.live.com:587 and use SSL to connect. In the Advanced settings, I checked "Send multiple commands to the server simultaneously" to speed up the sync process when the email is read. If you need more information, I think that the settings were similar to the FluentFactory mBox website instructions for setting up thunderbird.

There are still some syncing issues for me, but I can restart mBox easily to solve the issue.

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I found this fix, thought it might be useful if you still haven't found a fix. http://nicholasworkshop.wordpress.com/2011/07/24/mbox-mail-for-mac-on-lion-fix-works-with-apple-mail-5/

I'm gonna try tomorrow--since I have custom domains setup it might be a little more complicated than the regular @hotmail.com account. :S

Good luck!

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mBox has updated its product to work with OS X 10.6/7. I use Outlook in combination with mBox on Lion and it works like a charm.

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Access your hotmail acct, click on "options" at the top right corner, then "see all options", then make sure you select the Account tab.

Somewhere in the middle of the screen there is a blue link that says: Settings for POP, IMAP, and SMTP access...

Click on it and a card will appear with some info on it.

Download Sparrow, Add a new account, select IMAP and the enter the info provided in the card on hotmail.

SHould work!

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  • I do not see any such "see all options". When I hit "hotmail.com", I get redirected to "outlook.com". I am always confused by this. When I first got hotmail, it used to simply go to msn.com and then they changed it to go to hotmail.com and then live.com and then windowslive.com and now it goes to outlook.com. In anycase, when I login with my hotmail credentials in this new outlook.com, I see just a blue bar with a setting button on top right but I don't see anything called "see all options" in that button. Even if I go to "More Mail Settings" from there, I don't see any IMAP settings (only POP
    – pathikrit
    Commented Feb 9, 2013 at 1:38
  • I don't know how you can see IMAP settings - even Microsoft themselves admit they don't have it: answers.microsoft.com/en-us/windowslive/forum/mail-wlsettings/…
    – pathikrit
    Commented Feb 9, 2013 at 1:42
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TouchDown for OS X

TouchDown® for Mac is the very first ActiveSync enabled desktop client for the Mac OS/X platform. It provides Mac Users with push email against ActiveSync enabled servers.

OS X mail app and all famous apps including Outlook 2011 for Mac don't support Active Exchange, but TouchDown adds Active Exchange to OS X. However, this app is paid.

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Finally, Micro$oft now supports IMAP! Here is the IMAP settings from the horse's mouth:

Incoming IMAP Server: imap-mail.outlook.com Server port: 993 Encryption: SSL Outgoing SMTP Server: smtp-mail.outlook.com Server port: 587 Encryption: TLS

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0

What about using something like DavMail described here? You can run the software locally, on your box? Thunderbird with ActiveSync extension can work also, but if DavMail works (and there is no guarantee of course), you won't have to stray away from your favorite mail app.

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Setup your Hotmail account as an exchange account in the apple mail. The domain is m.hotmail.com.

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  • It does not work.
    – pathikrit
    Commented Aug 8, 2011 at 17:46

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