Strange Outlook 2007 SMTP Authentication Problem (Vista SP2 Issue?

J

Jarrod K.

I have a Vista Ultimate 64 powered laptop running Office Ultimate 2007. My
imap and smtp are running on two different Linux servers. Both connect using
SSL. This has worked without problems for more than a year. That is until
yesterday. After sending several emails, I noticed they all bounced with a
relay access denied error. A quick look in the Postfix (smtp) log file on the
Linux server indicated the problem. Outlook was making an anonymous
connection instead of authenticating. For security reasons, the server will
only relay for authenticated users.

Next I check the account settings in Outlook. Everything is correct, so I
click the "Test Account Settings" button and it works. I look at the server
logs again, and the test message authenticated properly. Ok, that was
strange, but now the problem is solved. Or so I think. I go back to Outlook
and start resending the emails that bounced, and they bounce again with a
relay access denied error. Back to the server longs and the connection is not
authenticating. Back to check account settings in Outlook again, and all is
well. The test message from the "Test Account Settings" button works fine. I
try sending the emails a third time, and the same thing happens all over
again.

So here is my question. Why would the test message sent when clicking the
"Test Account Settings" button in the Outlook account setup authenticate
properly, but sending actual emails out of Outlook not authenticate? I am
suspecting that this behavior is caused by Vista SP2 which I installed last
Friday. I had authentication issues with the IMAP side right after the
upgrade, but the problem went away after a second reboot. I can only conclude
that this problem is a result of SP2 for Vista, but other than that, I have
no idea why it is happening. There are no errors or warnings in the event
logs either.
 
J

Jarrod K.

No, I do not have a virus scanner integrated into Outlook. All email is
scanned on the server, so there is no need to have it in outlook. It is just
strange why the test message will authenticate, but actual email will not
when both supposedly used the same settings.
 
R

Roady [MVP]

Does it work correctly in Outlook Safe Mode?
Start-> Run; outlook.exe /safe
When you enable logging in Outlook, does it show Outlook uses
authentication?
 

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