> Have you also tried sending email from a non-root account?  The root
> user is "exposed" by default in Sendmail.  This means that the root user
> will *NOT* be masqueraded or remapped through genericstable.  You can
> see that the root user is exposed by looking at the {E} class:
> 
>     gothmog:/etc/mail# grep '{E}' sendmail.cf
>     C{E}root

That hasn't be the case since 8.10.0, released more than five years ago.
Giorgos, you should update your configuration.

8.10.0/8.10.0   2000/03/01
        CONFIG: Removed root from class E; use EXPOSED_USER(`root')
                to get the old behavior.  Suggested by Joe Pruett
                of Q7 Enterprises.

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