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When sending email with an attachment, Outlook attaches a system file and sends it rather than the file sent.

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by ah_pc2001

If the file that is sent is "winmail.dat" try this.
On the Tools menu, click Options, and then click the Mail Format (or "Send") tab.
Under the Send tab is the message format list, select Plain Text or HTML(NOT Rich Text Format), and then click OK.

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