Diggle (David Ramsey) may be content to spend the rest of his days in jail on Arrow, but his wife and best friend sure aren’t going to let him rot for a crime he didn’t commit.

After his corrupt fellow soldiers framed him for murder so they could get away with making some extra cash and not getting caught, Diggle decided that even though he didn’t do this particular crime, he still deserves to be in jail for killing his HIVE mind-controlled brother last season. He told his wife Lyla (Audrey Marie Anderson) exactly that when she visited him in prison, but she refused to agree with his dark and hopeless choice. In the very last scene of last week’s Arrow, “A Matter of Trust,” Lyla showed up in the Arrow cave to solicit Oliver’s (Stephen Amell) help in breaking Dig out of jail, and that’s exactly what they’re going to do in tonight’s all-new hour, “Penance.”

“I’m really excited for this episode since we’ve basically spent three episodes without Oliver and Diggle together, and Oliver and Diggle separated doesn’t really feel like Arrow to me,” executive producer Marc Guggenheim tells Nerdist. “In many ways, this episode is about what Oliver is willing to do for Diggle. We’ve seen all the things that Diggle is willing to do for Oliver over the years and the thing that I enjoy very much is watching Oliver return the favor.”

Executive producer Wendy Mericle echoed Guggenheim’s thoughts about getting to see a side to the Oliver/Dig dynamic that they usually don’t get to explore.

“It’s going to be an amazing hour. We’re going to see Oliver break Dig out of jail. It’s going to be gangbusters,” Mericle tells Nerdist. “It’s exciting. Dig is in a very complicated, emotional place and feeling very guilty about what he did in season four to his brother, and he’s got some very misguided ways of dealing with that. Oliver is going to snap him out of it. We like to flip that dynamic and we’ve earned that.”

And she knows that they weren’t able to tell this kind of story on the show before now. “Oliver has evolved,” Mericle says. “He’s become a more mature human being.”

Series star Ramsey is absolutely loving his character’s storyline this season because of how dark he gets to go. “It’s some pretty deep stuff,” Ramsey tells Nerdist. “Oh man. This week, he’s in prison still. Lyla wants to break him out, and let’s just say not everyone is down with that. So look forward to that.”

Another cliffhanger left over from last week’s jam-packed hour is the fact that Felicity (Emily Bett Rickards) finally confessed to new Team Arrow recruit Rory Regan aka Ragman (Joe Dinicol) that she is to blame for diverting Damien Darhk’s (Neil McDonough) nuclear missile to his hometown of Havenrock, completely decimating his home and killing everyone he knew and loved. Rory didn’t react to her confession, instead choosing to just walk away from her.

“I usually wish for more time in figuring out these concepts on this show, but we just don’t have the time,” Rickards tells Nerdist of exploring this storyline further. “We have less than 60 minutes to tell this story. We end that story and start a new one although she does wear that guilt in every episode and everything that she does now and moving forward. But the confession to Rory does really end that point of not being able to work cohesively as a team. And I loved working with Joe on that story.”

How Rory is going to react to Felicity’s confession, however, Dinicol warns that viewers won’t see it coming.

“I won’t tell you how he reacts but I will say he reacts in a way that you wouldn’t expect,” Dinicol tells Nerdist. “I actually really love how he reacts. It’s a real insight into the kind of person that he is. It’s really interesting. It’s very specific and it certainly adds a layer to his and Felicity’s relationship.”

As for how this is all going to affect his place on Team Arrow, knowing one of his leaders literally blew up his life, Dinicol explains that Rory has a big choice ahead of him.

“I think it’s a day of reckoning for him,” Dinicol says. “Being a fighter on this team is an opportunity for him to make a decision to move forward and start to deal with some of this tragedy and devastation in as positive of a way as he can or is he going to do what he did in his first episode, which is freak out and…try to kill or maim whoever wronged him. This is another instance where he’s being asked to let the angels of his better nature rule him and whether he does or doesn’t, we’ll see. His joining the team is a real turning point for him.”

And now that Oliver as Mayor of Star City has publicly announced his support for Quentin Lance (Paul Blackthorne) as his Deputy Mayor, expect the newly relapsed alcoholic to struggle with his new obligations and the pressure that comes with politics.

“He’ll handle this all with a stiff drink, I imagine,” Blackthorne jokes to Nerdist. “No, he’s got to get his act together at this point. He’s been given this much faith and responsibility by Thea [Willa Holland] and the others so he’s got to get himself together. We shall see if that’s the case.”

The pressure is going to mount higher than ever for the new recruits of Team Arrow this week as, in the midst of Oliver’s jailbreak mission, gangster Tobias Church (Chad L. Coleman) rears his head once more.

“It’s really fun to see the new recruits finally working together,” Madison McLaughlin, who plays new recruit Evelyn Sharp, tells Nerdist. “We have some fun stuff coming up. Wild Dog [Rick Gonzales] and Artemis and Ragman and Mister Terrific [Echo Kellum] are trying to get their footing, and Chad L. Coleman returns for a really fun arc as Tobias Church. And it becomes obvious that Artemis has Oliver as a mentor.”

What are you most excited to see from tonight’s episode of Arrow? Tweet me your thoughts at @SydneyBucksbaum!

Arrow airs Wednesdays at 8 p.m. on The CW.

Speaking of DC superheroes, check out our breakdown of Zack Snyder’s Justice League footage

Images: The CW