Reuven, I would look closely at my daemontools logging configuration. If it's setup correctly with multilog, you should see error log content being appended to "current" and it should roll according to the multilog options (see the error "run" file below).
I've included a portion of my own setup instuctions that you might use as a guide.
Hope this helps.
Config daemontools (as nsadmin)
$ cd ~nsadmin/servers/openacs4
$ cat run
#!/bin/sh
export AOLSERVER_HOME=/u1/aolserver
exec 2>&1
exec $AOLSERVER_HOME/bin/nsd -fzt /etc/aolserver/conf/openacs4.tcl -u nsadmin -g nsadmin
$ chmod +x run
$ cd log
$ cat run
#!/bin/sh
exec setuidgid nsadmin multilog s999999 ./error
$ chmod +x run
Place under daemontools control (as root)
# cd /service
# ln -s ~nsadmin/servers/openacs4 openacs4
# ps ax | grep openacs4 (until "supervise openacs4" appears)
# cd ~nsadmin/servers/openacs4
# chown -R nsadmin.nsadmin supervise log/supervise
# chmod -R g+rwx supervise log/supervise
REBOOT and check error logs