Outlook 2003 with SMTP Server (Win2003) not doing the windows authentication

[Jon Carlson]

I've got a Windows 2003 SMTP server with POP3 service. It was stable
and in use for a long time with Outlook 2000. I used the "Use Secure
Password Authentication" feature in OL2K, and I never had to store the
password in Outlook it always used my Windows login credentials. It
worked with both the POP3 and SMTP server.

For a variety of stupid reasons I tried to install Exchange 2003
(eventually got it working), upgraded to OL2003, found a bunch of
hassles with it, and then uninstalled Exchange. But I've kept OL2003
on the clients.

Now, I have plain old SMTP/POP3 back on my server and it seems to be
mostly working.

However, if I check the "Use Secure Password Authentication" in
OL2003, on one machine it doesn't work at all (error message to the
effect that the POP3 server won't do it), on one machine POP3 uses it
but SMTP won't (it'll eventually time out and fall back to using Basic
Authentication). And either case it requires storing the password in
the Outlook dialog box - it doesn't seem to be picking it up from my
Windows login.

Can someone tell me whether OL2003 is SUPPOSED to be able to log in
without having a password stored? Second, any other insights on what
might be screwing the whole thing up?

Thanks for any help!

 

[Jon Carlson]

Now both machines are behaving the same, so perhaps I was doing
something different on one or the other without realizing it. However,
here's what they are doing:

- SMTP won't do Windows Authentication. It'll either time out and
fall back to Basic, or I can disable it on the server and then the
clients don't go through the timeout but they obviously still only do
Basic.

- When I use SPA (for either or both POP3/SMTP), I must store the
password in OL2003 (or be prompted for the password each time OL2003
starts up). In OL2000 it would use the Windows login credentials.


Sorry for the long winded post and correction. Any thoughts still
appreciated. Thanks!

-Jon C.

 

[Steve Schofield]

I ran into something similar with Outlook2003, sorry never used Outlook
2000, the only way to get rid of the windows prompt was to use the VPN
client on Windows that had the credentials already stored. You might want
to ask this in an Outlook newsgroup.

--

Thank you,

Steve Schofield
Windows Server MVP - IIS
ASPInsider Member - MCP

http://www.orcsweb.com/
Managed Complex Hosting
#1 in Service and Support

 

[Jon Carlson]

Thanks for the reply Steve.

FWIW, I am on a private network, and I am logged into it (it's an
Active Directory network).

Still don't have any grasp on exactly what's going on. I'm starting to
wonder if some kind of Kerberos or NTLM configuration is turned on or
off at the networking level. Hmmm.

-Jon C.

 

[Steve Schofield]

Sounds good about being on an internal network. Is the login into your
machine the same account that is mapping to the Exchange box? If so, the
credentials logged into the box should authenticate you automatically to the
mail server. Usually the prompt is a stand-alone client using RPC over HTTP
to access a MAPI client.

--

Thank you,

Steve Schofield
Windows Server MVP - IIS
ASPInsider Member - MCP

http://www.orcsweb.com/
Managed Complex Hosting
#1 in Service and Support

 

[Jon Carlson]

I have one server (it's a small network). It runs Win2003 w/AD, SMTP
server, and POP3 server. My XP client machines log in via Kerberos (I
believe). OL2003 will prompt for the password unless I save it in the
OL2003 configuration dialog. The credentials are the same as my
Windows network (AD) login credentials. I don't think I'm using RPC
over HTTP (though I'm not sure how I would know for sure). In OL2000,
the credentials were the same, the server was the same (except for the
fact I tried Exchange, had some issues, and then uninstalled it), I
just never had to type them in.

Thanks for the help so far.

-Jon C.