Occasionally I have a very select set of users that would call in unable to send emails. When they click send they get "Cannot send this item". Simply copy pasting the contents into a new email would fix.
The common response on the internet is "switch to rich text", which I view as a workaround and at that one I don't like.
Thomas Vuylsteke posted this and has a great solution... Look at your network and ensure that you're not having network issues.
http://setspn.blogspot.com/2011/10/outlook-cannot-send-this-item.html
In my case it appears to have been due to Linksys devices at a few select desktops.
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