problem resolved! the account I was attempting to use to relay message
explicitly cannot relay messages. This is by design of our Net Admin.
Using an account the proper credentials, I was able to relay the
messages.

On Aug 12, 11:37 am, Jason Meckley <[email protected]> wrote:
> 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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