Is Docker compose installation required everytime I start a new session on docker CLI
When installing docker on windows or mac, there is a virtual machine called 'docker machine' that runs Linux OS. Docker has a command docker-machine used to start this virtual machine using docker-machine start. It is likely that every time you restart the toolbox, you start a new VM with new fresh copy of the OS. If you do docker-machine ls you should see multiple docker machines, one of them running. If instead on restart you always start the same docker-machine, it will have the previous changes, like previously installed packages, including the docker compose. You can give docker-machine start &lt;arg&gt; with the name of the docker machine you want to start, which should be always the same one.