550 You must SMTP Authenticate ...

[Minding]

Hi,

Over the past week, I've been receiving an error message when sending out
some emails using Microsoft Outlook 2002 SP3:
550 You must SMTP Authenticate before sending to <email address>

My IPS is Roadrunner and I have Norton Internet Security 2005.

I've experimented with the "Log on using Secure Password Authentication"
setting and the "My outgoing server (SMTP) requires authentication" and the
problem does not get resolved.

Can anyone help me understand why?

Thanks,
George

 

[Thomas Quester]

Hi,

There are many ways of authentication, you should find information of how to
authenticate at the providers web site.
Eventually you need to log on using ssl or just do pop before smtp (get
mails first, then send). Eventually you just have the wrong password.

Thomas Quester
www.olfolders.com

 

[Brian Tillman]

There are many ways of authentication, you should find information of
how to authenticate at the providers web site.
Eventually you need to log on using ssl or just do pop before smtp
(get mails first, then send). Eventually you just have the wrong
password.

"Eventually"? Don't you mean "Perhaps" or "Alternatively"?

 

[Minding]

Thanks for your thoughts.

What you're suggesting would require the problem to exist for every message
sent. It is not an "all the time" problem. The problem happens with some
messages/addresses and not with others. So it's not a password problem.
Since Outlook pops and smtps in the same order all the time, this is not the
problem.

My suspicion is that the error message is misleading and it's not actually
an authentication problem. Perhaps Norton Internet Security, except I've
disabled NIS and the problem persists. What else might it be?

G

Hi,

There are many ways of authentication, you should find information of how
to authenticate at the providers web site.
Eventually you need to log on using ssl or just do pop before smtp (get
mails first, then send). Eventually you just have the wrong password.

Thomas Quester
www.olfolders.com

 

[Brian Tillman]

My suspicion is that the error message is misleading and it's not
actually an authentication problem. Perhaps Norton Internet Security,
except I've disabled NIS and the problem persists. What else might it
be?

Norton is well-known for not actually disabling the mail scanning feature,
even when shown as disabled. You usually have to uninstall the product and
reinstall without that feature in order to truly disable it.

 

[Minding]

Then this is what I shall do and see if NIS is the cause. Thanks.

 

[Minding]

Back to the drawing board. I removed NIS and the problem persists. I'll
call my ISP again and try to recall what might have changed on my system
recently. It has to be one or the other since I've been emailing with MS
Outlook successfully forever and anon.

Any other ideas, however, are welcome.

Thanks.
George