Rodney, This is more of a suggestion than a technical issue. Everything is working as intended. It's just not efficient enough for your preference using your current game system. That said, I'll try and break down our design decision and what you can do. The reason it does't auto sort any of the initiatives, cards or numbers, is to keep the tracker system agnostic. Being system agnostic, meaning anything you could play on a tabletop you can play here, is very important to the Roll20 team. There are some tools in the development pipeline that may help speed up this kind of play, however they're not going to be available for a while. In the mean time, the optimal way to refine your game experience is with the API. If you're interested in becoming a mentor there are some very simple scripts that will allow you to reorder the tracker at the push of a button, and more complex initiative scripts that will re-deal a card to everyone already in the tracker or auto-reorder every time the tracker is changed. If you choose to become a mentor, send me a private message and I'll help you get the scripts you need to create the optimal game experience for you and your players.