Hello there, Long time not posting a question here, I hope someone has faced a situation as described in the following lines: Our current scenario has to deliver messages through Microsoft Business Productivity Online Services. It uses SMTPTLS so we had the choice to configure SMTPTLS directly on OTRS or to ask OTRS to deliver the message to the local MTA and configure this MTA to use SMTPTLS. We chose the second options since is the one in which we've witnessed more advance, not to mention postfix log is more verbose that OTRS log regarding message delivery. Here's the strange thing: When we try to deliver a message using index.pl?Action=AdminEmail or using the command-line, it is delivered, but when we try to deliver an auto-reply, the following message is written on the history: Sent no auto response - no valid email address found in From field. We've set OTRS on more than 30 scenarios on the past 5 years so we're pretty sure the auto-reply stuff is correctly configured, but we have no idea why this notification is not sent but AdminEmail and command-line ones are successfully sent. Any comment regarding this issue is highly appreciated. We just ran out of ideas. Thanks, Leonardo Certuche www.itconsultores.com.co Medellín, Colombia