Hmm. After comparing the log files, I think I may have found the issue: Jun 05 06:25:01 c CRON[8719]: (root) CMD (test -x /usr/sbin/anacron || ( cd / && run-parts --report /etc/cron.daily )) Jun 05 06:25:05 c runuser[8833]: pam_unix(runuser:session): session opened for user nobody by (uid=0) Jun 05 06:25:33 c runuser[8833]: pam_unix(runuser:session): session closed for user nobody Jun 05 06:25:34 c popularity-contest[8857]: unable to submit report to http://popcon.debian.org/cgi-bin/popcon.cgi. Jun 05 06:25:34 c popularity-contest[8858]: unable to submit report. Jun 05 06:25:34 c CRON[8718]: pam_unix(cron:session): session closed for user root
When it fails, it always does between 6:25 and 6:26 which is the time /etc/cron.daily is run. Maybe the popcon server is overloaded at that time and the 30s timeout in popcon-upload triggers?