fixed : What to do with a winmail.dat attachment ?

Question :

I recently received an eMail that should include various attachments, but it only included one : a winmail.dat file.

When I try to open it, OSX tells me there is no app on my Mac that can handle this file.

What can I do ?

Answer :

There are various ways of solving this. (or rather : ‘handling this’, as fixing the actual cause isn’t something an end user can do)

But first, a little insight into the cause :

Long ago, when eMails were still text-only without layout and attachments were added as plain files, a lot of eMail-client makers wanted to improve their user experience and provide their users a layout-option for eMails. Microsoft then developed TNEF as a protocol for communication between their Outlook eMail-clients. But TNEF never made it into an eMail-communication industry standard. HTML (the web-layout protocol) was adopted as the industry-wide standard. MS Outlook never fully adopted regular HTML as it’s eMail-layout protocol. So, even though Outlook calls them HTML-eMail, they are actually being sent as TNEF-eMail, which is HTML-ish, but still MS Outlook-only…

Sometimes (in the chain of eMail-servers involved in eMail-communication) the sender’s Outlook-app (or MS Exchange client) sends out a TNEF-eMail, not a regular HTML-eMail. All receivers of the eMail that use Outlook (or MS Exchange) will not detect any irregularity, but any recipient who’s not using Outlook as their eMail-client will receive it as a text-eMail with only one attachment : a winmail.dat file.

So… this is not a Mac-problem, it isn’t even a problem for all non-Outlook users, it is just that the only way to prevent this from happening to you, is to use MS Outlook…

…but for most non-Outlook users, using Outlook is not an option…

Anyway… the solution …or rather the various options for solving this, as either the sender can prevent this from happening, or the recipient can find ways to open the windmill.dat file anyway :

Microsoft provides 2 options for the sender who wants to prevent this :

1. set Outlook to only send ‘Plain Text’-eMail to any future recipient :

in Outlook, choose “File” (or “Tools”), then “Options”, then “Mail” (or “Mail Format”), and then in “Compose in this message format”, choose “Plain Text”, then click “OK”

2. set Outlook to only send ‘Plain Text’-eMail to this specific recipient :

in Outlook’s Address Book, double-click on the recipient’s eMail-address, then in the “SMTP – Address” field choose delete (un-click) the check-mark at “Always Send To This Recipient iIn Microsoft Exchange Rich-Text Format”, then click “OK”

More info can be found on Microsoft’s website :

http://support.microsoft.com/kb/290809

Even though prevention is the better option, there are alternatives : if you are a recipient using OSX, you can find various apps to unpack winmail.dat files in the Mac App Store. Too bad, there are no free apps for this in the App Store, but there is a FREE one available here :

TNEF’s Enough

If you prefer an automatically updated app from the Mac App Store, and don’t mind paying for it, consider this one, which will unpack faster and has a more comprehensive and visually nicer interface :

Winmail Extractor

If you also need a winmail.dat unpacker-app for your iPhone and/or iPad, you can consider this one :

Klammer for iOS & OSX

There are FREE services available online also, that will convert your windmill.dat for you instantly. Just keep in mind that by using them, you are enabling these services to view the contents of your eMail and it’s attachments, so you are willingly giving up your privacy in suing them. An example :

winmail-dat.com

But, again : even the windmill-dat.com service itself advices you to prefer a dedicated (offline) winmail.dat conversion app (on your Mac) over the use of their service.

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fixed : set IMAP eMail for Hotmail.com, Live.com and Outlook.com on iPhone/iPad

Question :

I would like to setup my Hotmail-eMail on my iPhone, but rather as an IMAP-account than as the usual POP-account.

Is there any way to do that in iOS ?

Answer :

Yes, IMAP eMail has finally come to Hotmail.com, Live.com and Outlook.com eMail.

To set up a Hotmail/Live/Outlook-eMail account on your iPhone/iPad, do this :

note : instructions for setting-up Hotmail/Live/Outlook-eMail on MacOSX can be found here.

if you’re running iOS 7 [ scroll down for iOS 6 and iOS 4.2.1 ] :

1- open the Settings app, go to “Mail, Contacts, Calendars” and in the “ACCOUNTS” chapter, click on “Add Account”

2- in the window that opens, click on “Outlook.com”

3- in the next window,  type your Hotmail/Live/Outlook-eMail address, your Password and any Description you like, then click “Next”

4- in the window that follows, select the options you want (at least keep “Mail” switched “ON”) and click “Save”

That’s it… congratulations ! 😉

if you’re running iOS 6 [ scroll down for iOS 4.2.1 ] :

1- open the Settings app, go to “Mail, Contacts, Calendars” and in the “Accounts” chapter, click on “Add Account”

2- in the window that opens, click on “Microsoft Hotmail”

3- in the next window,  type your Hotmail/Live/Outlook-eMail address, your Password and any Description you like, then click “Next”

4- in the window that follows, select the options you want (at least keep “Mail” switched “ON”) and click “Save”

That’s it… congratulations ! 😉

if you’re running iOS 4.2.1 (if you’re on an iPhone 3G ; iOS5.5 instructions for iPad 1 are expected to be very similar) :

1- open the Settings app, go to “Mail, Contacts, Calendars” and in the “Accounts” chapter, click on “Add Account”

2- in the window that opens, click on “Microsoft Exchange”

3- in the next window,  type the following :

at “Email” type your Hotmail/Live/Outlook-eMail address

at “Domain” type hotmail.com (if you have a Hotmail.com-eMail address)

at “Domain” type live.com (if you have a Live.com-eMail address)

at “Domain” type outlook.com (if you have an Outlook.com-eMail address)

at “Username” type your Hotmail/Live/Outlook-eMail address

at “Password” type your Hotmail/Live/Outlook-Password

and at “Description” type any description you like

then click “Next”

4- then the same window updates and an extra chapter appears named “Server”, it will be  automatically filled out with either m.hotmail.com or m.outlook.com ( and probably sometimes even m.live.com ) ; don’t bother, just click “Next”

5- in the window that follows, select the options you want (at least keep “Mail” switched “ON”) and click “Save”

That’s it… congratulations ! 😉

Note : if you want to change the settings of your Hotmail/Live/Outlook-accont in iOS, open the Settings app and go to “Mail, contacts, Calendars”, there you can click on the eMail-account you want to edit, and you will be able to change things like :

• “Mail Folders to Push” ; which mailboxes (besides your Inbox, so your Sent or even your Trash maybe) to Push (= auto-update) to your iPhone/iPad

• “Mail Days to Sync” ; how many days ‘backwards in time’ you want your iPhone/iPad to sync to Hotmail/Live/Outlook

• do you also want to sync your Contacts and/or Calendars to Hotmail/Live/Outlook ?

• do you want to change specific settings of the account itself ? (like the Server, SSL on/off, the Description, etc.)

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fixed : set IMAP eMail for Hotmail.com, Live.com and Outlook.com in MacOSX Mail.app

Question :

I’ve always though it was extremely annoying that Microsoft only allowed POP eMail for Hotmail.com for MacOSX, but I kept my Hotmail-account alive for al these years since I actually liked it, even after I switched to Mac…

Recently I heard that Microsoft is finally allowing IMAP access to Hotmail.com eMail, but I can’t figure out how to set it up on my Mac…

Can you please help ?

Answer :

Yes, you’re correct : IMAP eMail has finally come to Hotmail.com, Live.com and Outlook.com eMail.

Setting it up in MacOSX is not as straight forward as one might have hoped however…

The tricky part is that MacOSX will automatically set-up a POP-account if you are setting up a new account in Mail.app using a Hotmail.com, Live.com or Outlook.com eMail-address.

note : instructions for setting-up Hotmail/Live/Outlook-eMail on iPhone/iPad can be found here.

That being said…

If you follow these steps, you will be able to succeed anyway :

( if you are on OSX 10.9 Mavericks, read this first )

1- in OSX Mail.app, go to Preferences, then to Accounts and (if you have one) select your current POP-setup for Hotmail/Live/Outlook from the list, then go to the Account Information tab, and there un-check the “Enable this account” option

2- then use the Plus-button (bottom left) to add a new account

3- in the pulldown-window “Add Account” that appears, fill in your Full Name, type a fake eMail address ( e.g. nobody@blabla.com ) and leave the Password blank, then click on Create

4- in the next window, set the Account Type to “Exchange IMAP” (only if you don’t have that option choose “IMAP”) and use the following info, depending on what eMail-address you have :

for Hotmail.com-eMail, use :

Description : Hotmail IMAP ( or if you perfer your eMail-address, make sure to add “IMAP” or something like that to it, else it will conflict with your previously set-up Hotmail POP )

Incoming Mail Server : imap-mail.outlook.com [ will automatically select Port 993 ]

User Name : username@hotmail.com [ replace “username” by your own username ]

Password : ••••• [ your Hotmail-password ]

Outlook Web Access Server : m.hotmail.com

for Live.com-eMail, use :

Description : Live.com IMAP ( or if you perfer your eMail-address, make sure to add “IMAP” or something like that to it, else it will conflict with your previously set-up Live.com POP )

Incoming Mail Server : imap-mail.outlook.com [ will automatically select Port 993 ]

User Name : username@live.com [ replace “username” by your own username ]

Password : ••••• [ your Live.com-password ]

Outlook Web Access Server : m.live.com

for Outlook.com-eMail, use :

Description : Outlook IMAP ( or if you perfer your eMail-address, make sure to add “IMAP” or something like that to it, else it will conflict with your previously set-up Live.com POP )

Incoming Mail Server : imap-mail.outlook.com [ will automatically select Port 993 ]

User Name : username@outlook.com [ replace “username” by your own username ]

Password : ••••• [ your Outlook.com-password ]

Outlook Web Access Server : m.outlook.com

5- then click “Continue”, and if you get an error-message, just click “Continue” again

6- in the next window put a check-mark in front of “Use SSL”, set Authentication to “Password” and click “Continue” again

7- in the next window, use these settings :

for Hotmail.com-eMail, use :

Description : Hotmail SMTP ( or anything you like )

Outgoing Mail Server : smtp.live.com [ will automatically select Port 25 or Port 465 ]

you can check “Use only this server”, but it’s not obligatory

do check “Use Authentication”

User Name : username@hotmail.com [ replace “username” by your own username ]

Password : ••••• [ your Hotmail.com-password ]

for Live.com-eMail, use :

Description : Live.com SMTP ( or anything you like )

Outgoing Mail Server : smtp.live.com [ will automatically select Port 25 or Port 465 ]

you can check “Use only this server”, but it’s not obligatory

do check “Use Authentication”

User Name : username@live.com [ replace “username” by your own username ]

Password : ••••• [ your Live.com-password ]

for Outlook.com-eMail, use :

Description : Outlook SMTP ( or anything you like )

Outgoing Mail Server : smtp-mail.outlook.com [ will automatically select Port 587 ]

you can check “Use only this server, but it’s not obligatory

do check “Use Authentication”

User Name : username@outlook.com [ replace “username” by your own username ]

Password : ••••• [ your Outlook.com-password ]

8- then click “Continue” and if you get an error message, just click “Continue” again

9- in the next window, put a check-mark at “Use SSL”, select Authentication “Password” ( or “External (TSL client Certificate)” if you happen to have that ), and click “Continue”

10- in the next window, put a check-mark at “Take account online” and click on “Create”

11- then, back in Mail.app’s Prefecences, under Accounts, select your newly created eMail-account and click on the “Account Information”-tab and re-type your correct eMail-address in “Email Address:” (replacing the nobody@blabla.com you had originally entered) and check if all settings are as they need to be according to the above

12- then exit the Mail.app Prefecences (click the red button upper left) and click “Save” when the “Save changes” pulldown window appears

13- now, back in Mail.app itself (if you do not see the normal Mail window, go to File –> New Viewer Window), you will see the new Hotmail/Live/Outlook account has appeared, and it is looking for your old & new eMails on the Hotmail/Live/Outlook-mail servers

…most people will have lots of old eMails to import, so this might take some time (don’t be surprised if this takes 15, 20 or maybe even 30 minutes…)

14- if the import of the old & new eMails from the Hotmail/Live/Outlook-mail servers is complete, they will appear in the Inbox window and you’re done…

Congratulations !

…if you do not see your old & new eMails appearing, but you do see an “Unread eMails”-number next to the name of the Hotmail/Live/Outlook-inbox in the listing on the left, you have run into a bug in Mail.app that was only recently solved in OSX 10.8.5

to manually solve this problem, quit Mail.app, open Disk Utility (from the Applications –> Utilities folder), run “Repair Disk Permissions” on your Hard Drive’s main partition and when that’s finished, re-open Mail.app and all should be solved

Enjoy !

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