There are two problems that could be a factor here.could you elaborate more on why you said you should never have IIS and IMail installed at the same time? What problems/syptoms would I see in this case. How is port 80 figuring in Imail (other than webmail, webcalendar)?
The first is that you can't have both IIS and IMail both listen to port 80. However, if you don't mind having web messaging on another port (such as the default 8383), or you don't use web messaging, then this isn't an issue.
The second is that running IIS on the same server as IMail makes the whole server more open to attacks. If you use separate servers for IIS and IMail, and a spammer gets into the IIS server, you could block all E-mail from that server (which would only block legitimate mail being sent via IIS). If you have them both on the same server, you wouldn't have the option of blocking the mail without blocking all your outgoing E-mail. Also, a hacker would be able to gain access to any E-mail stored on the server, if they broke in through IIS. However, if IIS is up to date with all the latest patches (and you keep it up to date), this should not be much of an issue (but, few people keep IIS up to date!).
What is the domain that they are being sent to (so we can check to see if there is a DNS issue)?I have some issues with mail not getting delivered to users from certain domains; this may be a separate issue, maybe not?
When the E-mail is sent, does the sender receive a bounce message (if so, what does it say?)? Do your IMail SMTP log files show the delivery attempts?
-Scott
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