Thank you for the post. As of today, UCP agent is available only as Linux container. Because there is no UCP agent responding on Windows node, UCP manager will keep waiting. This is why it gets stuck at “initializing…”
I do not have the exact timeline, but I know we are already working on Windows container version of UCP agent along with few changes to facilitate the communication.
Not directly asnwering your question but try portainer/portainer image which provides UI for managing docker swarm and which fully supporting Windows containers.