Files within Docker bind mount directory not updating

Bind mounts are based on inodes and when the file is deleted and recreated then the bind-mount is broken. These changes aren't propagated to the bind-mount until a container restart so it picks the new inode.

A solution for this case (files are deleted and recreated) is to mount the parent directory instead, so in your case you can mount using -v /dev:/dev. Of course this will expose /dev to the container so handle it with care.