I had the same problem (on lucid) with a custom log file, In my case the
permissions were wrong: After changing them to user=syslog and group=adm
the reload works.

It seems that rsyslog is starting with root privileges and then dropping
them. That way it works on startup (and restart) but not on reload. A
reload of rsyslog is triggered by logrotate.

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https://bugs.launchpad.net/bugs/612900

Title:
  rsyslog does not reopen /dev/xconsole on reload

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