Hello all, Basic Setup info (for outgoing mail) running Exchange 5.5 on Win2K. I have an internal Bridgehead server that is setup to forward all mail to a GFI MailEssentials\Security Gateway(via IP) box for SPAM\Virus scanning. The GFI software then sends the mail using SMTP in IIS Issue: Our systems send on average 40,000 e-mails per day. Every day, at various times, I will look at my Performance Monitors for the queued outbound messages on the internal Exchange 5.5 bridgehead server. About twice a day, I will notice that the queue will show one message stuck in queue. If I let it sit there for about an hour, about 10 to 15 e-mails will queue up behind the other mail. Keep in mind, that our organization is still able to send and receive mail through this very same server(except for these random few messages that are queueing). When I look in the outbound queue in the Exchange Administrator then click on the message itself, the details screen appears. In the Recipients field it lists the destination address followed by [Host Unreachable]. If I delete the first message (by time submitted) the remaining queued messages are sent. My questions are: 1. what could be making mails queue up in the Exchange IMC if it is configured to send all e-mails to the GFI gateway server for delivery? 2. what would cause the random few messages to queue up behind this message even though 99% of e-mails are flowing as they are supposed to? 3. why would the Exchange IMC find the Host Unreachable since it is not setup to send mail other than directly to the GFI gateway IP Address? Weird issue... Thanks for any ideas. Chris