It's still wrong, and I don't know how I could explain it more completely: -ENTRYPOINT service ssh restart && bash +ENTRYPOINT ["service", "ssh", "restart"

It's still wrong, and I don't know how I could explain it more completely: -ENTRYPOINT service ssh restart && bash +ENTRYPOINT ["service", "ssh", "restart", "&&", "bash"] You should read and understand the documentation for the containerfile format before continuing. This isn't some quirk because i'm using &&, you are breaking almost every dockerfile that doesn't use the array syntax for ENTRYPOINT.