I seem to have most of my problems with updating for the first time in a year resolved (see below for one outstanding issue). Thanks to all those who assissted. Here's what I did. The order may not be as I did them. Also I'm not sure if they were all necessary, the stage2 bit for example. 1. Linked make.profile to the new dir lrwxrwxrwx 1 root root 48 Sep 24 13:21 /etc/make.profile -> /usr/portage/profiles/default-linux/amd64/2005.1 2. Downloaded and unpacked the stage2 tarball[Rupert Young] . I first backed up /etc and var/lib/portage and then restored them after. 3. Re-emerged the gentoo toolkit: gcc-config glibc binutils libstdc++ 4. Used gcc-config to point to the latest gcc 5. Updated env with etc-update env-update source /etc/profile 6. Did all the updates I could think of emerge --sync emerge -u portage emerge -upDv world emerge -uDv world emerge -upv system emerge -uv system Now everything is in sync and up to date. However, the old gcc is still being picked somehow when trying to emerge -av net-im/gaim. It should be pointing to 3.4.4. Any ideas where this is being set? What is the gentoo equivalent of the environment variable LIBRARY_PATH? grep: /usr/lib/gcc/x86_64-pc-linux-gnu/3.4.1/libstdc++.la: No such file or directory /bin/sed: can't read /usr/lib/gcc/x86_64-pc-linux-gnu/3.4.1/libstdc++.la: No such file or directory libtool: link: `/usr/lib/gcc/x86_64-pc-linux-gnu/3.4.1/libstdc++.la' is not a valid libtool archive make[2]: *** [libenchant_aspell.la] Error 1 make[2]: Leaving directory `/var/tmp/portage/enchant-1.1.6/work/enchant-1.1.6/src/aspell' make[1]: *** [all-recursive] Error 1 make[1]: Leaving directory `/var/tmp/portage/enchant-1.1.6/work/enchant-1.1.6/src' make: *** [all-recursive] Error 1 !!! ERROR: app-text/enchant-1.1.6 failed. Rupert Young