You should be able to update roundup. It's actually not quite as easy as I expected it to be, but it should go something like this:

su - roundup -c "pip3 install 'roundup==2.1.0' --user"

That should complete with the following message:

Successfully installed roundup-2.1.0

Note that you will also probably see a warning like this:

  The scripts roundup-admin, roundup-demo, roundup-gettext, roundup-mailgw, roundup-server and roundup-xmlrpc-server are installed in '/home/roundup/.local/bin' which is not on PATH.
  Consider adding this directory to PATH or, if you prefer to suppress this warning, use --no-warn-script-location.

Instead of adding the path, we put symlinks in /usr/local/bin (which is in the path). So you can safely ignore that.

Then the next step is to migrate the DB:

roundup-admin -i /var/lib/roundup/tracker/ migrate

And update the config:

roundup-admin -i /var/lib/roundup/tracker/ updateconfig /etc/roundup/tracker-config.ini

We also need to adjust some permissions. Plus, the layout of the roundup package appears to have changed quite significantly in v2.1. So we need to update quite a few paths. I am using quite a few variables, which makes it look a bit more complicated than it is really (you should be able to just copy/paste this into your terminal):

# set some vars
RT_TRACKER=/var/lib/roundup/tracker
RT_LOCAL=/home/roundup/.local
LOCAL=/usr/local
PY_V=$(python3 --version | sed "s|^.* \(3\.[0-9]\+\).*|\1|")
RT_VER=2.1.0
LIB_PY=lib/python${PY_V}
SHARE=$RT_LOCAL/$LIB_PY/site-packages/usr/share
DOCS=$SHARE/doc/roundup/html
# set permissions
chmod -R 0775 $RT_LOCAL
chmod -R 0774 $SHARE
SUB_DIRS="_images _sources _static"
for dir in $SUB_DIRS; do
    chmod o+x $DOCS/$dir
done
dir=$DOCS
while [ "$dir" != "$(dirname $RT_LOCAL)" ]; do
    chmod o+x $dir
    dir=$(dirname $dir)
done
# create symlinks
ln -sf $RT_LOCAL/$LIB_PY/site-packages/roundup $LOCAL/$LIB_PY/dist-packages/roundup
ln -sf $RT_LOCAL/$LIB_PY/site-packages/roundup-$RT_VER.dist-info $LOCAL/$LIB_PY/dist-packages/roundup-${RT_VER}.dist-info
ln -sf $SHARE/doc/roundup /var/www/docs
ln -sf $SHARE/man/man1  /usr/local/share/man/man1
# finally update apache config to serve docs from new location
sed -i "s|$RT_LOCAL/share/doc/roundup/html|$SHARE/doc/roundup/html|" /etc/apache2/sites-available/roundup.conf

Now all you should need to do is restart Apache:

systemctl restart apache2

No problem. Glad to hear that it worked (eventually) for you.

Thanks for following up on that and great to hear that you finally worked through it and it appears you are good to go now.

Please do not hesitate to drop in again if you have any further issues, questions or suggestions for us.

My guess is that python has thrown an error. If I'm right, then there should be a stacktrace in the Apache log. You should find the Apache log /var/log/apache2/error.log. I.e. something like this (to show last 20 lines of log):

tail -20 /var/log/apache2/error.log

If you are unsure, feel free to post the output and I may be able to give some ideas. Although please note that I may not get a chance to respond until Monday.

To be honest, I wasn't at all clear where an issue like this would come from. 'AttributeError' is part of the Python standard library so seeing an error saying that it is not defined seemed crazy to me.

However, I did a bit of googling and came across a very similar wsgi error (it's Django running on Ubuntu, but close enough for our purposes). Graham (the mod_wsgi developer) explains the likely problem. Although that more explains the actual underlying issue, not the direct cause in your scenario. Reading on, it seems that it may be related to a lazy loaded module. TBH, I'm not 100%, but I suggest first adding the 'WSGIApplicationGroup %{GLOBAL}' directive (as Graham suggests here) to your Apache config. I'd give that a go (add it to /etc/apache2/sites-available/roundup.conf, I suggest under the existing 'WSGIScriptAlias' line) and restart Apache:

systemctl restart apache2

If the issue continues, then please add in the 'LogLevel info' directive (again in /etc/apache2/sites-available/roundup.conf) and restart Apache again. Then try to recreate the issue and post the log again and we'll see what we can see. Hopefully that might asist us to understand a bit more.

There is still a chance that we may need to call on the assistance of the Roundup guys again, but perhaps we can work it out?!