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For those who aren't so technical, I'll fill in some details for the original poster. First, you're going to want to start the Terminal app. In my Launchpad, it's in the "Other" folder; on older macs I've had, it was in a folder called Utilities (which was in the Applications folder). Once that's started up, cut and paste the following commands, one line at a time. The first one will pause at one point to ask for your password (this is the password you use for your Mac). There will be lots of messages that scroll by. usr/bin/ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)" brew install wine winetricks export WINEARCH="win32" export WINEPREFIX="${HOME}/.wine32" winetricks dotnet40 cd ${WINEPREFIX}/drive_c/Program\ Files unzip ~/Downloads/Hero\ Designer.zip I modified his instructions a bit for myself to add: cd echo "#\!/bin/sh" > run_pine.sh echo export WINEARCH=\"win32\" >> run_pine.sh echo export WINEPREFIX=\"${HOME}/.wine32\" >> run_pine.sh echo wine \${WINEPREFIX}/drive_c/Program\ Files/Pine\'s\ Hero\ Designer/Hero\ Designer.exe >> run_pine.sh chmod +x ./run_pine.sh Then, when you want to run the hero builder, you should be able to open a terminal window and just type ./run_pine.sh I basically did the above and it appeared to work for me (at least I got something that looked like the hero builder; I haven't yet started playing around in it). I can't promise that this doesn't install any malware on your computer or that it will work for you, and I also can't promise I will check the forums with any frequency to answer questions.