I was able to find out more.
my credentials correctly entered will successfully send the email
my credentials incorrectly entered will fail with a SmtpException:
Failure sending mail.
admin credentials correctly entered will fail with a
SmtpFailedRecipientException: Mailbox unavailable. The server response
was: 5.7.1 Unable to relay for [email protected]. I also review the status
code "MailboxUnavailable" which means The destination mailbox was not
found or could not be accessed.

At this point I think I need to get my network administrator involved
to answer some questions.

If anyone has any insight into the problem it would be greatly
appreciated.

On Aug 12, 9:12 am, Jason Meckley <[email protected]> wrote:
> 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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