Matt, I've seen similar messages in my installation, but due to my OTRS box being in a different domain than my Exchange box and having a bad mx record for my Exchange box, resolved by adding an entry to my Exchange box in the OTRS server's host file. I'd look there first, make sure you can connect to the SMTP service via telnet <your Exchange server> 25 from your OTRS install and authenticate with the account you are using for SMTP. Check your Exchange box's SMTP logs and see if that provides any detail about what the problem is. Also, be sure you have the right SMTP settings in the config.pm file. I've found that on a Windows install, the SMTP settings in the GUI don't change the settings in the config file, but rather show what is there. Ken ================ Hello List, I am attempting to evaluate OTRS and have it installed on a Windows 2003 server. I am unable to get outbound mail to work using an internal SMTP relay server (Exchange) and have verified that there is no authentication or communication issue with my SMTP server from the OS on the server that OTRS is installed on. Associated otrs.log file entries are: [Fri Aug 7 11:16:14 2009][Error][Kernel::System::Email::SMTP::Send][92] Can't connect to osmtp.snagajob.com: Bad file descriptor! [Fri Aug 7 11:16:14 2009][Notice][Kernel::System::Ticket::Event::NotificationEvent::_SendCustomerNotification] Sent customer 'Ticket Closed' notification to 'MMR1 mailto:mmr1@snagajob.com >>'. My belief is that the system does in fact connect to the SMTP server because if I specify a host name that does not exist, I get a different error message. Has anyone else run into this and resolved it? I've checked online to no avail... Thanks! -Matt ================