Unable to send authenticated SMTP messages?

K

Kevin Gray

Using Entourage 2004... The whole story is kinda lengthy so I'll do my best
to sum it up. When I'm at work I get the following error when sending
through "any" SMTP server that uses authentication...

"Authentication failed because Entourage doesn't support any of the
available authentication methods."

Now after searching Google extensively for this error message I found an MS
technote... http://support.microsoft.com/default.aspx?scid=kb;EN-US;842882

The problem I have is that I can send messages fine through this very same
account (.mac account) with the same settings if my laptop is at home. It's
only when I go to work or a T-mobile hotspot that I get these errors. So it
can't be something between Entourage and the SMTP server, right? It has to
be something getting in the way of that communication and blocking
authentication for this email account. Another thing to note is that I have
another email account that is through a hosting company and I can send
authenticated messages through that account from work just fine IF I'm
sending on Outlook Express on PC. If I send from Entourage through that
account with the same exact settings then I get the same error as above.

Any ideas? I've seen a lot of posts about this, but no real help from
anywhere.

Thank you!
 
C

Corentin Cras-Méneur [MVP]

The problem I have is that I can send messages fine through this very same
account (.mac account) with the same settings if my laptop is at home. It's
only when I go to work or a T-mobile hotspot that I get these errors. So it
can't be something between Entourage and the SMTP server, right?
Click to expand...

It looks like T-Mobile is blocking the SMTP port. It doesn't surprise me that
much since ISPs tend to be picky on SMTP because of spammers.

To workaround these issues, I enabled Postfix on my Mac to use it as my own
SMTP. It is nevertheless possible that T-Mobile would also use the ports
Postfix uses.


Corentin
 
K

Kevin Gray

Thanks for the response. However, I have the same issue at work and our
sysadmin says ports 110 and 25 are wide open. I've been looking for some
kind of open SMTP server that I could use that wouldn't require
authentication - then I could switch to this when at work and still send,
but I cannot find any.
 
C

Corentin Cras-Méneur [MVP]

Thanks for the response. However, I have the same issue at work and our
sysadmin says ports 110 and 25 are wide open. I've been looking for some
kind of open SMTP server that I could use that wouldn't require
authentication - then I could switch to this when at work and still send,
but I cannot find any.
Click to expand...


Not a big surprise... Good SMTP servers should never be left active without
any kind of authentication outside their domain.
So what about enabling Postfix on the Mac itself ??
You'll find information here:
http://www.entourage.mvps.org/exchange/postfix.html
and if you don't want to do it manually there is a shareware that does it for
you:
http://www.cutedgesystems.com/weblog/Tutorials/PostfixEnabler.html


Corentin
 
T

Timberfish

Not a big surprise... Good SMTP servers should never be left active
without any kind of authentication outside their domain.
So what about enabling Postfix on the Mac itself ??
You'll find information here:
http://www.entourage.mvps.org/exchange/postfix.html
and if you don't want to do it manually there is a shareware that does
it for you:
http://www.cutedgesystems.com/weblog/Tutorials/PostfixEnabler.html


Corentin
Click to expand...

Hi Corentin, I just wanted to take a moment to thank you very much for
your time and effort and also tell you that the issue is now resolved.
It turns out that our new Firewall was set to block authentication by
default. How about that? It's always the simple things. Still not
sure why Outlook Express got around that setting though. I guess we'll
never know.
 
C

Corentin Cras-Méneur [MVP]

Hi Corentin, I just wanted to take a moment to thank you very much for
your time and effort and also tell you that the issue is now resolved.

Great!!

It turns out that our new Firewall was set to block authentication by
default. How about that? It's always the simple things. Still not
sure why Outlook Express got around that setting though. I guess we'll
never know.
Click to expand...


Weird.... Especially since usually settings require authentication instead of
blocking it. I'm glad you found out what was wrong.


Corentin
 
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