Note that wine compiles twice for 32bit and 64bit use and as such requires compat-32 ports tree to be enabled to work. You could edit wine to only compile 64bit only but then you can only run PE64 bit binaries. You enable compat-32 by. mv /etc/ports/compat-32.rsync.inactive /etc/ports/compat-32.rsync $EDITOR /etc/prt-get.conf And add: prtdir /usr/ports/compat-32 Also be sure to enable: runscripts yes