There's plenty room for bugs in mechanism like that. For example Motorola Droid (back in 2010) was locked and only accepted signed updates. There was a bug where you could bypass it by using authentic update and appending your payload at the end of that file.
Interesting, can you point me to a news article or link? Shouldn't that have been rejected as an improperly signed file as (update+payload) should have a different signature than (update)? I'm want to know whether I'm misinterpreting something, misunderstanding something, or the signatures were misimplemented.