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• if your mail is not leaving the queue folder, check out KB #273644
• if your mail is not leaving the pickup folder, and you are getting smtpsvc Event ID: 535 ("Virtual Server : The drop directory , for * could not be created.") in your event log, see KB #288538
• make sure SMTP Virtual Server is running in Internet Services Manager
• check the event log for SMTP Service events
• turn on logging for your SMTP server, to see if the mail is even being attempted to be sent to the server
• make sure your smarthost and FQDN are configured correctly
• make sure your smarthost allows you to relay unconditionally (some require authentication)
• make sure your server can resolve the ip of your smarthost name - try using the IP of your smarthost to see if this is the issue
• restart the SMTP Service (or IIS altogether), and if that fails reboot the server, to see if this clears up the backlog
• make sure you are sending from / to a valid address / domain
• check any .rtr files in the \queue\ folder - these can be caused by various mistakes in code or config
• check the server itself by setting up outlook express on the machine, using the same settings, and attempting to send mail
• if the machine is behind a firewall/router, make sure it has access to port 53
• you might also check any 3rd party software; e.g. one user had Kerio running on his server and, to prevent spam by his users, it was limiting the SMTP server to 20 messages per hour... anything over this would sit in the queue until the next hour
• make sure that your disk has enough space to hold the messages; one reader wrote in that they had this problem when they were using a smart host, and the smart host had a full C: drive... so make sure to check for problems on all machines in the chain