If you try to update an entity's passengers, it will not update, even if it says it did.
Try to replicate:
/summon Cow
/entitydata @e[type=Cow] {Passengers:[{id:"Pig"}]}
If you try to update an entity's passengers, it will not update, even if it says it did.
Try to replicate:
/summon Cow
/entitydata @e[type=Cow] {Passengers:[{id:"Pig"}]}
duplicate of MC-66115