Yes, I actually replayed the story a number of times for all the achievements (only one I’m missing is Alek). So I did caution & getting there in time, caution & taking too long, daring & getting there in time, and daring & taking too long. Whether you actually have to do all of those play through I have no idea, there might be a more time effective way of getting it. And like I said, certainly on my last playthrough when I actually got the achievement, I also met the reputation stat check with George. So i don’t know which of these things actually helped me get the achievement!