When starting and attaching to a container with a pseudo-tty, the initial bash prompt will only appear if the 'attach' request comes very quickly after the 'start' request (<0.1 seconds, in my tests).
Note how in the first run (attach immediately after starting), a chunk is received containing the prompt, but in the second run (start, then sleep 1s, then attach), it hangs after receiving the response headers.
This is an issue when trying to run a bash container from a Docker client that is geographically distant from the Docker server - the prompt doesn't appear, and you have to hit Enter to get one. From a UX standpoint, it appears as if Docker is simply hanging, which is pretty frustrating!