I also just tested it with Content-Type, same problem. So likely also other 
headers. 

But these headers have to actually be duplicated. Im guessing mailop itself 
doesn’t do that, it only over signs. Many senders do add duplicate headers, and 
we mostly see this with Mime-Version for some reason. 

My guess, MS first “fixes” the header to remove the duplicate, and then 
verifies the signature, which then obviously doesnt validate anymore.  I’m 
inclined to say “sender problem”, but this is happening with some pretty large 
senders.

cor

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