Outlook likes putting attachments and other crap in a stupid attachment called ‘winmail.dat’. Request-tracker doe not like this and neither do I. On debian, install the ‘ytnef’ package. ‘/usr/bin/ytnef-filter’ appears to be the ‘ytnefprocess.pl’ script metioned in the README file. Make sure you’ve got the perl package MIME requrements. I didn’t have to but you may need to install the ‘libmime-perl’ package. Then modify your RT email configuration to look like this: helpdesk: "|/usr/bin/ytnef-filter|/usr/bin/rt-mailgate --queue helpdesk --action correspond --url http://rt.example.com" helpdesk-comment: "|/usr/bin/ytnef-filter|/usr/bin/rt-mailgate --queue helpdesk --action comment --url http://rt.example.com" That’s two lines altogether. Wordpress sucks with this stuff. It’ll filter out the attachments it can, the useful ones like actual file attachments and leave the rest alone, like the proprietary MS crap. ...