After fresh cvsup of ports tree and reading contents of UPDATING, attempts to portupgrade python to latest in ports tree fails as follows: 


# portupgrade -R python-2.4.3
--->  Upgrading 'python-2.4.3' to 'python-2.5' (lang/python)
--->  Building '/usr/ports/lang/python'
===>  Cleaning for python25-2.5
===>  Cleaning for python-2.5
===>  Vulnerability check disabled, database not found
===>  Extracting for python-2.5
===>  Patching for python-2.5
===>  Configuring for python-2.5
--->  Backing up the old version
--->  Uninstalling the old version
--->  Deinstalling 'python-2.4.3'
--->  Preserving /usr/local/lib/libpython2.4.so.1 as /usr/local/lib/compat/pkg/libpython2.4.so.1
[Updating the pkgdb <format:bdb_btree> in /var/db/pkg ... - 50 packages found (-1 +0) (...) done]
--->  Installing the new version via the port
===>  Installing for python-2.5
===>   python-2.5 depends on file: /usr/local/bin/python2.5 - not found
===>    Verifying reinstall for /usr/local/bin/python2.5 in /usr/ports/lang/python25
===>  Vulnerability check disabled, database not found
===>  Found saved configuration for python25-2.5
=> Python-2.5.tgz doesn't seem to exist in /usr/ports/distfiles/python.
=> Attempting to fetch from http://www.python.org/ftp/python/2.5/.
Python-2.5.tgz                                100% of   10 MB  222 kBps 00m00s
===>  Extracting for python25-2.5
=> MD5 Checksum OK for python/Python-2.5.tgz.
=> SHA256 Checksum OK for python/Python-2.5.tgz.
===>  Patching for python25-2.5
/bin/mkdir -p /usr/ports/lang/python25/work/Python-2.5/portbld.static /usr/ports/lang/python25/work/Python-2.5/portbld.shared/Modules
/usr/bin/sed -e '1s,^.*$,#!/usr/local/bin/python2.5,'  /usr/ports/lang/python25/work/Python-2.5/Tools/scripts/pydoc > /usr/ports/lang/python25/work/pydoc2.5
/usr/bin/sed -e '1s,^.*$,#!/usr/local/bin/python2.5,'  /usr/ports/lang/python25/work/Python-2.5/Tools/scripts/idle > /usr/ports/lang/python25/work/idle2.5
/usr/bin/sed -e '1s,^.*$,#!/usr/local/bin/python2.5,'  /usr/ports/lang/python25/work/Python-2.5/Lib/smtpd.py > /usr/ports/lang/python25/work/smtpd2.5.py
/usr/bin/sed -i.bak -e  's,/usr/doc/python-docs-,/usr/local/share/doc/python,g'  /usr/ports/lang/python25/work/Python-2.5/Lib/pydoc.py
/usr/bin/sed -i.bak -e  's|^\( *prefixes = .*\)\]$|\1, "/usr/X11R6"]|g'  /usr/ports/lang/python25/work/Python-2.5/Lib/site.py
/usr/bin/sed -i.bak -e  's|^    \(..ASDLGEN.*\)$|       true|g'  /usr/ports/lang/python25/work/Python-2.5/Makefile.pre.in
/usr/bin/sed -i.bak -e  's|*\(..INSTALL_SCRIPT.*\)python-config$|#port \1|'  /usr/ports/lang/python25/work/Python-2.5/Makefile.pre.in
/usr/bin/sed -e 's|^#!.*|#!/usr/local/bin/python2.5|'  /usr/ports/lang/python25/work/Python-2.5/Misc/python-config.in > /usr/ports/lang/python25/work/python2.5-config
/usr/bin/sed -e 's|^#!.*|#!/usr/local/bin/python-shared2.5|'  /usr/ports/lang/python25/work/Python-2.5/Misc/python-config.in > /usr/ports/lang/python25/work/python-shared2.5-config
echo "fpectl fpectlmodule.c" >> /usr/ports/lang/python25/work/Python-2.5/portbld.static/Modules/Setup.dist
cannot create /usr/ports/lang/python25/work/Python-2.5/portbld.static/Modules/Setup.dist: No such file or directory
*** Error code 2

Stop in /usr/ports/lang/python25.
*** Error code 1

Stop in /usr/ports/lang/python25.
*** Error code 1

Stop in /usr/ports/lang/python.
*** Error code 1

Stop in /usr/ports/lang/python.
** Command failed [exit code 1]: /usr/bin/script -qa /tmp/portupgrade.37250.0 env PORT_UPGRADE=yes make reinstall
egrep: /var/db/pkg/python-2.4.3/+CONTENTS: No such file or directory
--->  Restoring the old version
** Fix the installation problem and try again.
[Updating the pkgdb <format:bdb_btree> in /var/db/pkg ... - 51 packages found (-0 +1) . done]
** Listing the failed packages (*:skipped / !:failed)
        ! lang/python (python-2.4.3)    (install error)
--->  Packages processed: 0 done, 0 ignored, 0 skipped and 1 failed
** Could not clean up temporary directory: Directory not empty - /var/tmp/portupgradet9F1h5Hh
#

Fix: 

Don't know
How-To-Repeat: Cvsup ports tree
Attempt to portupgrade python to latest in ports