Why is this happening? We are seeing Milchick push back against Lumon and adopt a softer approach for those he manages. He realised it wasn't Mss Huang that complained about his use of big words, that he's aware of Jame's predatory interest in wintertide students and sends her far away where it's safe. He sees that innie Dylan's love for his outie's wife, and takes pity on him when he resigns.. as demonstrated in the Kier Pardons his Betrayers painting; Milchick is pardoning Dylan.