A New York plaintiff who settled a copyright lawsuit against several news outlets, including Time Inc., Breitbart News Network, Vox and Yahoo, over a photo he took of football player Tom Brady and manager of Boston Celtics basketball team Danny Ainge has struck again. This time he’s filing suit against a radio company in Florida federal courts.

It’s a case that could test the boundaries of an emerging area of copyright law, raising major questions about how media companies incorporate social media posts into online stories.