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Article ID: KWin0097
Added:  9/22/09 BC
Updated:  11/05/09 AF/SS

SMTP Authentication

Since RDP products don't pass authentication to an SMTP mail server, a local SMTP server is used.  If a customer needs authentication, there is an option.  However, this option makes e-mails sent by RDPWin prey to the rules of the authenticated e-mail server where the mail is relayed. 

This process may resolve problems with spam, since the relaying of the mail will be through a legitimate mail server for the customer’s domain.

Steps for Authentication to Another SMTP Server

  1. Log into the computer that is running the SMTP server used by RDPWin.

  2. Go to IIS -> Default SMTP Virtual Server -> Right click and go to Properties.

  3. Select the Delivery tab and Click the Advanced... button.

  4. In the smart host field enter the qualified name of the authenticating SMTP server that is offsite (i.e.  If an IP address is to be used, the entry within this field must in the format: []  (Notice the use of brackets around the IP address).

  5. Once an entry has been placed within the smart host field, the option of ‘Attempt direct delivery before sending to smart host’ becomes available.  DO NOT CHECK THIS.  All mail should go to the authenticating SMTP server.  Click OK to return to the Delivery tab.

  6. Click the Outbound Security button to access the Outbound Security screen.  **See notes on Outbound Security.  This step may not be necessary.

  7. Select the type of authentication needed.  Most customers use Basic authentication.

  8. Enter the user name and password required to authenticate on the outside authenticating SMTP server and click OK to save.

  9. Click Apply and OK to save the settings on the Delivery tab.

Try a test e-mail from RDPWin.  RDPWin should send the mail to the internal SMTP server and reply with a successful delivery message.

Some external SMTP servers used by customers may limit their use by static IP.  There may be no user name and password.  RDP recommends not using the IP or name of this external SMTP mail server directly within RDPWin because in some cases delivery response is delayed.

Outbound Security:  To avoid issues with RDPWin timing out while waiting for delivery, it is recommended that RDPWin is directed to an internal SMTP server that relays the mail to the external server without any ‘Outbound Security’.  The ‘Outbound Security’ steps could be skipped in this instance.

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