Penny is seen standing with Ironwood and a group of other Atlesian military personnel in the Volume 2 Opening of Rwby. He is then revealed later that volume, to have assisted and sponsored her father in her creation. He hopes that she will one day be able to save the world. Penny is also seen following Ironwood around in volume 3, chapter 3 while waving at Ruby. It is also revealed that Ironwood personally chose all the members of Penny's team to specifically to keep an eye on her.
In volume 7 chapter 12, after Penny along with Winter heard Ruby's warning about Ironwood's plan to abandon Mantle, she seems very disturbed and shocked about his plan. After Penny becomes the new Winter Maiden, she decides to abandon Ironwood and sides with Ruby and her friends. In volume 8 chapter 1, Penny gets a call from Ironwood. She answers his call where she hears him ask her to return to Atlas. Ruby then takes her scroll and answers back that Penny isn't going anywhere until he changes his mind about Mantle.
Penny becomes visibly distraught when Ironwood says that if Salem gets through Atlas' defenses, everything that follows will be her fault, and Ruby comforts her. In "Refuge", she explains to Ruby how Ironwood's words were weighing on her, saying that people would die because of her. Ruby then says ironwood was only trying to hurt her and reassures her she made the right decision. In chapter 9, Ironwood then threatens Penny again saying that if she doesn't surrender herself to him he would bomb all of Mantle. She then decides to go to him and when they meet face to face, Ironwood exasperated, tells her she did the right thing while putting his hand on her shoulder.
Iron maiden is a rare pair within the RWBY fandom. Mainly because most people ship her with Ruby. Also because of the age gap between the two, the fact that Penny's a robot and also the fact that they're enemies now. Since Ironwood's now gone off the deep end. Some fans have even jokingly refered to it as the iron giant.
- "Iron Maiden" comes from Ironwood's surname, and Penny being the Winter Maiden.