I would guess it's a lot easier and less risky to find a few vulnerabilities than to successfully exploit them and get away with it at the first attempt. After

I would guess it's a lot easier and less risky to find a few vulnerabilities than to successfully exploit them and get away with it at the first attempt. After all, even his previous "successful" escape resulted in him being shot and recaptured and years added to his sentence, and his colleague being killed. It also sounds like he really wants to spend more time with his girlfriend and her son, while he was single during his previous escape.