SMTP Authentication Issue

[chillysnow]

Hi,

I'm running Wingate 6 on an XP server, and one of the users is having intermittent problems with sending emails using Outlook.

All the other users of the system connect from the LAN side and have the server's internal IP address in the SMTP box in Outlook. I believe all the other users are unaffected by this issue.

This user however sometimes connects remotely and so has the server's domain name in the Outlook settings rather than the IP address.

This user attempts to send an email and gets a "relaying denied" error. He attempts a second or third time and get the same result, but the message gets sent on the fourth attempt. All of these attempts occur within a few seconds. Occasionally the email goes first time.

The history window in Wingate shows a relaying denied message for each failed attempt, with the user shown as "guest". The attempt that worked shows the correct username. So it's clearly an issue with Wingate thinking that the user is a guest rather than in the database.

The problem occurs whether connected via the LAN or remotely. It also occurs whether the "my server requires authentication" box is ticked or not.

Any clues?

Many thanks

Mark Elliott

[adrien]

Hi

Sounds like the client is connecting to the external interface of WinGate.

This will treat him differently than if he was connecting to the Internal interface, since the external interface is by default untrusted.

An easy way around the issue in the office would be to add the user's IP address as an assumed user. Then the client IP would be trusted.

For external access, the client will need to authenticate. If the client has the setting "my server requires authentication" set, and it still isn't happening, it's likely that the authentication itself is failing. This can be for a number of reasons - the way to really find out what is going on is to enable debug logging on the SMTP server, and check in the log files.

Adrien