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Winmail.dat is Going to Send Me to a New Place!

This information is an exerpt from

How to Prevent Winmail.dat Attachments from Being Sent in Outlook

By Heinz Tschabitscher, About.com Guide

Do random recipients of your teachers emails, seemingly out of the blue, complain about a mysterious attachment called "winmail.dat", which they cannot open, no matter what they try?   We find that this generally occurs when teachers on on Windows machines using Exchange Outlook send emails to parents that have a MAC.   

It's Outlook's fault, in a way-- or the recipient's email client's??? If Outlook sends a message using the RTF format (which is not very common outside Outlook) for bold text and other text enhancements, it includes the formatting commands in the winmail.dat file. Receiving email clients that do not understand the code therein display it as a stale attachment. To make matters worse, Outlook may also pack other, regular file attachments in the winmail.dat file.  We seem to have this occur when teachers attach a PDF?  Of course without going to each recipients home and sitting with each sender, it is hard to know all of the details.

Fortunately, you can get rid of winmail.dat altogether by making sure Outlook does not even try to send mail using RTF.

Prevent Winmail.dat Attachments from Being Sent in Outlook

To prevent Outlook from attaching winmail.dat when you send an email:

1.      Click File in Outlook.

2.      Select Options.

3.      Go to the Mail category.

4.      Make sure HTML or Plain Text is selected for Compose messages in this format: under Compose messages.

5.      Now make sure Convert to HTML format or Convert to Plain Text format is selected for When sending messages in Rich Text format to Internet recipients: under Message format.

6.      Click OK.

Prevent Winmail.dat Attachments in Outlook 2002-2007

To make sure Outlook 2002 to Outlook 2007 do not attach winmail.dat files:

1.      Select Tools | Options... from the menu.

2.      Go to the Mail Format tab.

3.      Under Compose in this message format:, make sure either HTML or Plain Text is selected.

4.      Click Internet Format.

5.      Make sure either Convert to Plain Text format or Convert to HTML format is selected under When sending Outlook Rich Text messages to Internet recipients, use this format:

6.      Click OK.

7.      Click OK again.

8.      Disable Winmail.dat Stubbornly Going to Particular Recipients No Matter the Default

The standard settings for outgoing mail formats in Outlook can be overridden per email address. So, on a per case basis — when somebody complains about an inexplicable "Winmail.dat" attachment after you have made all the right settings changes —, you may have to reset the format for individual addresses:

Search for the desired contact in your Outlook Contacts.

1.      Double-click the contact's email address.

2.      Alternatively, click on the desired email address with the right mouse button and select Open Outlook Properties... or Outlook Properties... from the menu.

3.      Make sure either Let Outlook decide the best sending format or Send Plain Text only is selected under Internet format:.

4.      Click OK.

Extract Files from Winmail.dat without Outlook

If you receive winmail.dat attachments with embedded files, you can extract them using a winmail.dat decoder on Windows or OS X.