PlayOnLinux or Wine not working

A few things:

  1. Did you install WINE and PlayOnLinux using Synaptic Package Manager (SPM)? SPM can be accessed through System Tools. If you don’t have it installed, type in terminal: sudo apt install synaptic
  2. In SPM, click Search and type PlayOnLinux. My version is 4.3.4 as yours should be. The latest WINE release is 5.0.2
  3. I recommend updating WINE after removing the old version first.
    a. Removal of old WINE - Use the following commands, in sequence, in terminal:
    sudo apt-get remove wine
    rm -rf $HOME/.wine
    rm -f $HOME/.config/menus/applications-merged/wine*
    rm -rf $HOME/.local/share/applications/wine
    rm -f $HOME/.local/share/desktop-directories/wine*
    rm -f $HOME/.local/share/icons/???_*.xpm
    sudo apt-get remove --purge wine
    sudo apt-get update
    sudo apt-get autoclean
    sudo apt-get clean
    sudo apt-get autoremove
    b. Installing WINE: Use terminal commands listed here. You will use the Ubuntu 18.04 version command. You will install the Stable branch package.