Calico

This achievement was a little glitchy for me and did not unlock right away. It's technically story related so it's unmissable and I did do everything required so I know I wasn't missing anything. Once the path cleared to Cutie City, I continued playing for a little while in hopes that it just was late to unlock. I thought about starting a new game but didn't want to be to hasty since starting over seemed more like a chore. Once I was done playing I shutdown my Xbox, the next day I logged back in and as soon as I started the game and was able to take control of the character the achievement unlocked. What I would suggest doing, is making a save after you have made all the deliveries and have talked to Ash telling him they are all done before you head up to Freya's to meet her, Maia, and Ash and talk to the Construction Cats, just in case. If it doesn't unlock turn off your console and log back in and try again, it should unlock.