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I'm trying to use MS Word and Outlook 2003 to send a bunch of emails with attachments but apparently this option is not allowed.

¿Any clean way to do this?

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Here is an article that is on point for you: Mail Merge to E-mail with Attachments ...

This procedure can be used to mail merge to e-mail, including attachments with each message when Microsoft Office Outlook is installed. It has been used with all versions of Office from Office 97 up to and including Office 2007.

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