Docker stuck on "Waiting for SSH to be available..."

Use the switch --native-ssh

for example docker-machine --native-ssh .... Get more details from here

Problem here is by default docker uses DockerNAT network switch. You should create a new external network switch instead. This issue is covered here and here. You can create an external network switch using the below command

docker-machine create -d hyperv --hyperv-virtual-switch external-switch tempbox1

or you can create one through the UI

Be sure to reboot the device after creating the external switch.

I had a similar issue and non of the solutions worked. Turns out that according to this answer, docker launches SSH with Unix specific elements. This is said to have been fixed in the releases that followed, but I still encountered the 'Waiting for SSH' issue. I resolved this by simply using GIT bash to run all docker related SSH commands.