You have to install IIS on any machine which you use to send mail via WebMail, according to something I read recently. I encountered similar problems, and reverted back to sending mail through Outlook.
Outlook is a bit of a pain as the security kicks in every time you try to send a mail, using a developed application, but there is a handy little utility and its freeware called CLICKYES to work around this. It allows you to send a mail without having to click Yes to Outlooks security messages, and is configurable, so you can talk to it in .NET to put it in Suspend or Ready Mode.
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