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I feel like this is a stupid question but:

I have a test environment set up where I need to enable SMTP basic authentication with IIS. I have a Win2k3 r2 server as a DC in its own windows domain called testdom.local. I also have the MS pop3 server set up with the testdom.local domain on that server. I have a windows account called "simon" on that domain and a mail box set up on the pop3 service.

With anonymous access set up on the IIS smtp server, I can send an email from a client to the server which will arrive in the simon mailbox. If I turn on basic authentication on the SMTP server, I can not get the mail client (outlook 2003) to authenticate.

I have followed what is said here:

I have tried:

  • the domains "testdom" and "testdom.local" in the default domain box in the SMTP authentication properties.
  • Using the logon names "simon", "simon@testdom.local" and "testdom\simon" in the logon properties on the mail client.
  • I have tried specifying smtp authentication using "use same settings as my incoming server" and manually specifying the account details.

What am I doing wrong? I feel like I am missing something really obvious!

Please note: This is a test environment, I have a requirement to use SMTP basic auth, so I am not interested in using any other authentication option. I have made sure Integrated Windows and SPA auth are turned off on client and server, and I have double checked the password is right because the pop3 works to collect the mail.

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I had this exact same problem and the issue turned out to be that I was trying to authenticate using the Administrator account. As soon as I tried a non-administrative user account it started working perfectly.

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Thanks... I will look into this and get back to you. – simon Feb 23 '12 at 15:40
Sorry will get back to you I promise... I need to get some time on our test rig, as soon as I do I will report back. Thanks :) – simon Mar 2 '12 at 14:50

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