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In regards to the 'Post via Email' feature, does anyone know of a way to send an attachment with it? In this case it would be a PDF document.

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There are a few plugins that offer that capability. Look at Postie for example.

Austin Passy did presentations at a couple WordCamps last year demonstrating how to set up the plugin. There's a video on wordpress.tv of his presentation at WordCamp PDX.

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According the the Codex

Posting by email does not support attachments and any attachments sent with the email will appear in their raw form in the blog post.

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I think the question is how to add support for attachments, not whether or not the posting by email feature currently does support attachments. – editor Feb 9 '11 at 21:34

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