[Windows Containers] different entrypoint+exec between docker versions, same DockerFile

Docker Desktop
1

I’m having a Dockerfile similar to this

FROM mcr.microsoft.com/windows/servercore:10.0.17763.437
COPY . .
COPY WindowsContainerStartupScript.ps1 C:\\scripts
WORKDIR c:\\assets
ENTRYPOINT powershell ls && 
CMD cmd /c tasklist

when I build that on my dev machine (version 19.03.5), I get the following on docker inspect image

 "Cmd": [
                "cmd",
                "/S",
                "/C",
                "#(nop) ",
                "CMD [\"cmd /S /C cmd /c tasklist\"]"
            ],
            "ArgsEscaped": true,
            "WorkingDir": "C:\\assets",
            "Entrypoint": [
                "cmd /S /C powershell ls &&"
            ],

when I build the same Dockerfile on another machine (version 18.09.6), I get the following

 "Cmd": [
                "cmd",
                "/S",
                "/C",
                "cmd /c tasklist"
            ],
            "ArgsEscaped": true,
            "WorkingDir": "C:\\assets",
            "Entrypoint": [
                "cmd",
                "/S",
                "/C",
                "powershell ls &&"
            ],

Problem with the first one is that on

docker run myImage:myTag cmd /c anyCommand

it will always fail with the message “container 6dc24a8608a164d1570eac47c01355e0e1707098e8818184c1332824705b2687 encountered an error during CreateProcess: failure in a Windows system call: The system cannot find the file specified.”

Is this a bug? Should I file it somewhere?
Any suggestions on how to run two commands during container start? I want to run a Powershell script and as soon as it completes launch another process selected by user.