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In Outlook 2003 and 2007, there was an option to choose the preferred message format on a per-contact basis. It's explained here: http://office.microsoft.com/en-us/outlook-help/change-the-message-format-to-html-rich-text-or-plain-text-HP001232996.aspx#BM3

I'd like to find this specific option in Outlook 2010. Can someone point me in the right direction?

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For Outlook 2010:

In the Contacts Folder

To turn off TNEF, follow these steps:

    Open the recipient's record in the Contacts folder.
    Double-click the recipient's email address.
    The Contact Card appears. Click View more options for interacting with this persona, and then click Outlook properties.
    Choose Send Plain Text only in the Internet Format list. 

 To send in TNEF, follow these steps: 

    Open the recipient's record in the Contacts folder.
    Double-click the recipient's email address.
    The Contact Card appears. Click View more options for interacting with this person , and then click Outlook properties.
    Click Send Using Outlook Rich Text Format in the Internet Format box.
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It should be noted that this works differently when using the Outlook Hotmail Connector. If I click on Outlook Properties in the contact card of a contact in my Hotmail/Windows Live account, the dilaog that comes up is completely different and only has a checkbox for "Use Microsoft Outlook Rich Text Format for this recipient". –  PersonalNexus Feb 16 '12 at 19:46
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Also, if using Exchange, this is not available for those contacts in the same organization as the sender. –  CharlieRB Feb 16 '12 at 19:57
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