Sorry to be still on this subject. I don't understand how others aren't suffering the same problem. I have only seen one other, and there are a lot of PostFix boxes out there. Problem: Postfix sends to Exchange Server that is behind ISA with default SMTP Application filter enabled. ISA Server rejects the connection with a 500 5.3.3 Unrecognized command response. I have installed Postfix server here and had a play. From Netmon I have seen that Postfix sends MAIL FROM: RCPT TO: and DATA: commands all in one go, unlike other servers I have looked at, which send one at a time. I have tried extending the allowed lengths of commands in the filter but it is no good. The only resolution was to disable the filter and now it works. Is anyone else out there running a mail server behind ISA with SMTP Application filter enabled? I can test sending a message from our postfix server and see if you get it. It would be appreciated. Thanks Jon