>> Some ISPs can do a POP before send authentication.  That is you have to
>> check your POP account first and then for some period of time after that,
>> your IP address is considered "authenticated" and you will be allowed to use
>> the smtp server to relay.  I have our email server at work set up like this
>> so people who use clients that do not support SMTP AUTH can still use our
>> smtp server from home.
> 
> So it sounds as if Richard does need SMTP AUTH and is getting the benefit of
> it on the second attempt since the first attempt does check the POP account
> using the correct password. (I recall that Yahoo once worked like this.)
> 
> So if Richard goes to Tools/Accounts/this account, and clicks the long
> button that says "Advanced Sending Options" just below the SMP Server
> setting at the very bottom of the window, then checks the "SMTP server
> requires authentication" box and leaves the radio button at "Same settings
> as POP" without filling anything else in, he should now be able to send
> first time without getting that error.

Maybe, maybe not.

"POP before SMTP" and "SMTP Auth" are two separate forms of SMTP
Authentication.  A given ISP might support none, one, or both forms (and
SMTP Auth potentially may take multiple forms itself).

"POP before SMTP" was invented so as to not require any client changes.  And
as most email clients attempt to download immediately upon launch, it works
transparently most of the time.  Until you try to send email without first
checking it. ;-)

"SMTP Auth" required client changes; however, most current mail clients now
support the functionality so it's considered the preferred method.


It's worth trying to see if it avoids the "first relay fails" scenario;
however, there's no guarantee that it'll work.

mikel

PS:  See <http://www.sendmail.org/~ca/email/auth.html> for far too much
information.


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