This question probably has more to do with the SMTPclient than MR, but
I figure I'll start here since MR is used to configure the SMTP
client.

The usage scenario is simple. click a button, process data, send an
email (with an attachment). The application uses Windows
Authentication and Windows Integrated Security for single sign-on.
Everything works without an issue if the email is sent within the
domain. If I try to send to an external domain (send email from
[email protected] to [email protected]) I get the 5.7.1 cannot relay error.

So my next step was to provide a username and password to
authenticate(authorize?) the message being sent. The first account I
tried was our administrator account. I figured this account is a start
simply because the account has full access to everything. If I can get
this to work i could then step down to more restricted account. But,
the administrator account failed. After a lengthy guess & test period,
using various combinations of domain, username and passwords for the
administrator account, I decided to use my credentials for SMTP
authentication/authorization. This time it worked. my MR configuration
looks like this

<monorail useWindsorIntegration="true" smtpHost="the exchange server"
smtpUsename="..." password="...">
  view engine...
</monorail>
<system.web>
   <identity impersonate="true" />
   ...
</system.web>

Next thought: this works under my credentials because I'm doing the
testing. Maybe the credentials work because my identity is
impersonated on the server. So I logged onto the application as
administrator with my credentials in the MR configuration.  And the
email was sent without a problem.

This works on the testing server because we are simply testing, but
for production I will need to use an account like the administrator's
account to configure the SMTP client. I cannot figure out the
difference between my account, which succeeds, and the administrator's
account, which fails.

Right now all my efforts are on the programming side. I haven't looked
at any of the infrastructure (exchange, active directory, etc) to see
if there are any configuration differences. I wouldn't even know where
to being.

Does anyone have experience solving this problem?

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