Long time lurker, first time poster... Ok, going to do a bit of a sum up here. The issues you are seeing are most likey caused by a firewall on the user side, either on the machine or their ISP. A lot of ISP's won't allow residental users to send email out on port 25. Since you don't know what port is allowed, you'd have to have the user configure your app. Not a good idea. Or it could be a local firewall blocking the message because it doesn't know your app is allowed to send. Again, a configuration by your user would need to occur, and again, not a great idea, especially if you don't like support calls. I'm with those that think it's a bad idea to use an SMTP transport to send an error message for an app outside of your network (we use smtp extensively inside our network), mainly because of security concerns. The username/password combo is used to authenticate a relay of the email message. This is bad to use outside of your network because someone could reverse engineer your code, find the username and password and start spamming through your mail server. If you insist on using SMTP, I would do a TRY CATCH to make sure the app can handle its own error and maybe set a counter to try more then once, then give up. You would also create a text file that you could have the user send to you as a backup. If I was doing this, I'd probably look at creating a web service that the client app can send the message to and have it then emailed to me and/or inserted into a database. The issue there might be that the user has to approve the outbound request, but that shouldn't be too big of a deal. If you need a web service sample, let me know. Cheers, Mike