I am using Docker Toolbox on Win 7.
Here is the error I get:
Error checking TLS connection: Something went wrong running an SSH command!
command : ip addr show
err : exit status 255
output :
Error getting IP address: Something went wrong running an SSH command!
command : ip addr show
err : exit status 255
output :
docker is configured to use the default machine with IP
When do you get that error? I found this issue https://github.com/docker/toolbox/issues/317 it describes something like your error.
They resolved recreating the default machine. Are you able to try this stuff?