Initially Jamie I'd look out for odd signature blocks and HTML which isn't well formed in LANDesk terms. We have had all sorts of problems with outlook signatures where people have done legitimate things, but which result in the emails not being process or only being partially processed.
I fully believe that is the issue is the signature block. It's so random that that is the only conclusion I can think of. Nice to see if confirmed from someone else.
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The only way I've seen one of our clients confirming this (anonymous of Canberra knows all) is to take one of the errant emails and forward it in some way using the mail client so that the mail server manipulates the data to be 'OK'. If you do track one of these down and are using outlook, you can save the email as a .MSG file and send it to LANDesk for them to check. Touch the email in any way (like forwarding it) and it will then work.
Yikes. Thus the reason I am pushing to get all Users using Self Service. NO MORE SIGNATURES!