As summary. I've tried both i686 and x86_64 mingw-w64, and using the winnt profile (and subdirs) as make.profile in /usr/$sysroot/etc/portage, and copying the embedded profile and modifying it as the wiki suggests. Reproducible: Always Steps to Reproduce: 1. emerge crossdev 2. Various instructions followed exactly from the wiki 3. crossdev -t {i686,x86_64}-w64-mingw32 4a. ln -s /usr/portage/profiles/prefix/windows/winnt /usr/$ARCH-w64-ming32/etc/portage/make.profile 5a. emerge sys-libs/zlib 4b. copy the embedded profile, remove ARCH, ELIBC, KERNEL from PROFILE_ONLY 5b. set said variables in profile/make.profile 6b. emerge zlib Actual Results: a. ARCH is not set/make.profile symlink complaints b. make -f win32/Makefile.gcc no such file when it does exist Expected Results: Compiled and installed zlib to my prefix