Getting perl scripting to work needs a few things: - configure with --with-perl-staticlib - libperl.dll is required in linking and running irssi, it's normally located somewhere around /usr/lib/perl5/5.6.1/cygwin/CORE/libperl5_6_1.dll copy it to eg. /usr/bin/libperl.dll - -DUSEIMPORTLIB is needed to be defined while compiling src/perl directory. It doesn't hurt to be defined everywhere, so configure irssi with: CFLAGS='-DUSEIMPORTLIB' ./configure --with-perl-staticlib