"Could not connect to server" error when accessing Outlook 2003 vi

[LindaD]

Hi,

I'm looking for help with a problem that I'm working on. I have a user who
uses Remote Desktop to connect to her office computer and check her email in
Outlook 2003 SP3. She is unable to send (SMTP) or receive emails (POP3) and
when testing the account settings, we get the following errors:

Log onto incoming mail server (POP3): Outlook could not connect to the
incoming mail server (POP3). The problem could be your SSL or port setting
for the incoming server. Verify your port and SSL settings under More
Settings on the Advanced tab.

Send test e-mail message: Outlook could not connect to the outgoing mail
server (SMTP). The problem could be your SSL or port setting for the
incoming server. Verify your port and SSL settings under More Settings on
the Advanced tab.

The interesting aspect of this problem is that if I reboot the computer and
then RDP into it, the test of the account settings works fine and emails are
sent and received without a problem. But if I then close Outlook, log off
the computer and reconnect again with RDP, the errors recur until I reboot
the computer again. I have tested RDP from home as well as from within the
network. It is not a firewall or anti-virus issue as I've tested with them
both disabled. The problem does not occur if I physically sit at the
computer and check email. This started happening about mid June and I have
no information from the user on what might have changed.

I have enabled logging in Outlook but do not see anything revealing in the
resulting log.

Does anyone have any ideas on what might be happening or where I should be
looking?

Thanks in advance for your help and suggestions.

Linda

 

[Hal Hostetler [MVP P/I]]

If you have an Anti Virus scanner on this machine and its setup to scan
email, disabling the email scanning feature is often not enough to stop
problems the scanner might be causing (this is particularly true with both
Norton and McAfee products); you should try uninstalling the application and
doing a custom re-install without any email scanning modules. You do not
need email scanning anyway; it is redundant, all it does is cause problems,
and the system will still be fully protected without it, provided the
resident file system scanner is kept up to date.

Hal
--
Hal Hostetler, CPBE -- (e-mail address removed)
Senior Engineer/MIS -- MS MVP-Print/Imaging -- WA7BGX
http://www.kvoa.com -- "When News breaks, we fix it!"
KVOA Television, Tucson, AZ. NBC Channel 4
Live at Hot Licks - www.badnewsbluesband.com

 

[LindaD]

Thanks so much for the suggestion Hal. I had pretty much ruled out
Anti-virus as a cause of the problem since it worked fine if I was sitting
right at the computer. However, I thought I'd post what DID end up solving
the issue.

For whatever reason, I had to enable SSL for both POP and SMTP to get it
working. Perhaps when you connect via RDP, you have to use SSL. In any
event once SSL was enabled, it would work. I also did have to import our
server's self-signed certificates because I would get the following message
in Outlook.

---------------------------
Internet Security Warning
---------------------------
The server you are connected to is using a security certificate
that could not be verified.
A certificate chain processed, but terminated in a root certificate which is
not
trusted by the trust provider.

Do you want to continue using this server?
---------------------------
Yes No
---------------------------

I had a hard time pinning down the exact steps to take to do this so I
figured I'd include that information in this update for others who might
struggle like I did.

1. Opened IE.
2. Went to Tools > Internet Options > Content tab
3. Clicked on Certificates button and chose Import.
4. Browsed to the certficate that I had saved down from our site and clicked
OK.
5. When asked what store to put it into, browsed and chose Trusted Root
Certification Authorities.
6. Got a pop up warning that the certficate could not be verified and said OK.

Thanks again for the response Hal. I truly appreciate that you took the
time to try to help me out.

Linda

--
Linda
Golden, CO

If you have an Anti Virus scanner on this machine and its setup to scan
email, disabling the email scanning feature is often not enough to stop
problems the scanner might be causing (this is particularly true with both
Norton and McAfee products); you should try uninstalling the application and
doing a custom re-install without any email scanning modules. You do not
need email scanning anyway; it is redundant, all it does is cause problems,
and the system will still be fully protected without it, provided the
resident file system scanner is kept up to date.

Hal
--
Hal Hostetler, CPBE -- (e-mail address removed)
Senior Engineer/MIS -- MS MVP-Print/Imaging -- WA7BGX
http://www.kvoa.com -- "When News breaks, we fix it!"
KVOA Television, Tucson, AZ. NBC Channel 4
Live at Hot Licks - www.badnewsbluesband.com

 

[Brian Tillman]

For whatever reason, I had to enable SSL for both POP and SMTP to get
it working. Perhaps when you connect via RDP, you have to use SSL.
In any event once SSL was enabled, it would work. I also did have to
import our server's self-signed certificates because I would get the
following message in Outlook.

Remote Desktop Connection shouldn't be a factor. As far as the machine
where Outlook is installed is concerned, it shouldn't care whether the
person is actually at the keyboard or using Terminal Services to connect.