A Fine Line: Distinguishing Issue Ads From Advocacy : NPR

Political scientists say the line between issue ads and express advocacy has almost been erased.

Not so many years ago "we could more easily put particular ads into buckets," says Deborah Jordan Brooks, a government professor at Dartmouth College who studies political attack ads. "Ads that are largely issue-based often have a real personal zinger right in there, and it may just be one line. Or ads that, you know, really have a lot of personal zingers in there still have some issue content." 
Campaign finance lawyer Robert Kelner says he is not surprised by the vagueness. Ultimately, he says, it's all about free speech.
"The price that we pay for the benefits of the First Amendment is that we have to essentially give a pass to some ads that you and I would probably agree look an awful lot like a campaign ad," he says.
via npr.org