On Tue, Apr 09, 2013 at 10:59:15AM -0400, Kevin Holleran wrote:
>    I am having sporadic email trouble when updating tickets. Sometimes it 
> sends, sometimes it
>    doesn't... here is a snippet of the log.

This doesn't really seem RTIR specific - it's probably a subject for
rt-users.

>    Apr 9 10:46:37 ir sendmail[1729]: r39Ekb3j001729: r39Ekb3k001729: DSN: 
> "AdminCc of
>    [2]DOMAIN.COM Ticket #19":;... List:; syntax illegal for recipient 
> addresses

I'm going to guess you've enabled this config option:
http://bestpractical.com/rt/docs/latest/RT_Config.html#UseFriendlyToLine
which is documented not to work on sendmail(tm).

-kevin

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