To paraphrase a classic Randy Newman ditty: Raymond Reddington has got a friend in Harold Cooper.

Tonight’s episode of The Blacklist (NBC, 9/8c) will find Cooper taking the stand at Red’s first hearing since getting arrested, and TVLine has an exclusive sneak peek at the tense interrogation.

As seen in the video above, Cooper’s testimony takes an uncomfortable turn when he reveals a few details of Red’s immunity deal with the FBI. The prosecutor is (rightfully!) skeptical that a seasoned criminal like Red would ever comply with the FBI’s strict rules — and when Cooper is asked if Red has committed any crimes since the immunity deal began, he’s not sure how to respond.

According to series creator Jon Bokenkamp, Cooper will come to a complicated moral crossroads this season, as he debates whether to defend Red or let the prosecutors take him down.

“As this case is gobbled up by bigger and bigger fish at a federal level, Cooper is really in the crosshairs of what to do,” Bokenkamp teases. “And he’s a very moral guy, but he’s really going to be saddled this season, in a strange way, with having Reddington’s back. There’s another one of those power shifts where Red — who is only ever telling Cooper however little he wants him to know — is now depending on this man to help navigate a criminal court system and prison system that are absolutely ready to gobble him up.”

Press PLAY above to watch our sneak peek of Episode 3, then drop a comment below with your thoughts.