Outlook Winmail

Outlook Winmail.dat files

Go in Outlook to Tools -> Options and select the Mail Format tab. On that tab, near the top, you'll see a "Compose in this message format" option. The choices are: HTML, Rich Text, and Plain Text. I'm betting yours is set to HTML and his is set to Rich Text. If so, his needs to be changed to HTML and that should do it.

Just to be perfectly certain, you can also click the "Internet Format" button on the same tab. In the middle of the new box, there's a drop-down menu relating to Rich Text options. I had mine set to "Convert to HTML format". That way, if for some reason I was writing a Rich Text message, it was converted to HTML format automatically before sending.

In case you don't know, winmail.dat is a file created by Outlook when you're sending a message in Rich Text format. In the world of real Email, there's no such thing as HTML messages or Rich Text messages. Those formats were added later. Originally, there was only plain text (and it's too bad we didn't stay with it because we'd have an awful lot less malware). HTML messages are really plain text messages with an attachment. Each attachment has a content-type field identifying what kind of attachment it is. For instance, a picture would have a content-type of image/jpeg. An HTML attachment would have a content-type of text/html. In fact, when I look at your message, to which this is a reply, your message has two parts to it. Part 1 was text/plain and part 2 was text/html. They both had the same content, except the HTML version had all the extra HTML stuff in it. (This is why purists don't like HTML email because it more than doubles the size of the email.)

So, what's winmail.dat? It's an attachment that contains the formatting instructions from the Rich Text formatted email. Only Outlook knows how to read it. When they made Outlook originally, they thought it would only be an email client for the Exchange (email) server. So, since everyone was connecting to an Exchange server, they thought everyone would be using Outlook. And, if everyone's using Outlook, why not allow emails to be sent in Rich Text format, which allows for greater control over the look of your document/email? Unfortunately, it (the winmail.dat attachment) really only works when both people using Outlook and going through an Exchange server.

Incidentally, I never liked using Word to edit email. It seems like overkill. To me, it's akin to getting your typewriter out to leave a note for your wife that you've gone fishing. Just give me a pencil and a post-it note. :-) (Besides, there are such things as macro viruses, too.)

There is one more thing that might be causing this. On the toolbar above the "To" field, notice another place to select HTML, Rich Text, and Plain Text. You need to make sure that's set to HTML too.