I've run into a problem where easy_install/setuptools continues to recommend upgrading itself even after the upgrade has been installed. Steps to reproduce on CentOS 5.2: include ~/python in PYTHONPATH include ~/bin in PATH create ~/.pydistutils.cfg [install] install_lib = ~/python install_scripts = ~/bin $ easy_install flup ... Running flup-1.0.3.dev-20090608/setup.py -q bdist_egg --dist-dir /tmp/easy_install-rPyZ6a/flup-1.0.3.dev-20090608/egg-dist-tmp-pm0o4x The required version of setuptools (>=0.6c9) is not available, and can't be installed while this script is running. Please install a more recent version first, using 'easy_install -U setuptools'. (Currently using setuptools 0.6c5 (/usr/lib/python2.4/site-packages)) error: Setup script exited with 2 $ easy_install -U setuptools ... Processing dependencies for setuptools $ which easy_install ~/bin/easy_install $ python -c 'import setuptools; print setuptools.__version__' 0.6c9 $ easy_install flup ... Running flup-1.0.3.dev-20090608/setup.py -q bdist_egg --dist-dir /tmp/easy_install-WoxTch/flup-1.0.3.dev-20090608/egg-dist-tmp-oFotRt The required version of setuptools (>=0.6c9) is not available, and can't be installed while this script is running. Please install a more recent version first, using 'easy_install -U setuptools'. (Currently using setuptools 0.6c5 (/usr/lib/python2.4/site-packages)) error: Setup script exited with 2 At this point I thought it might be a problem with flup's setup.py or ez_setup.py, but manually running python setup.py bdist_egg outside of easy_install works fine.