no route to host w/ outlook but not w/ thunderbird

[Nytridr]

I have a very strange problem.

I can send mail and everything else with thunderbird, squirrelmail, and even through command line, but I can not send mail using outlook.

When ever I try to use outlook to send mail I get the following error in my mail.log

Jan 3 14:31:21 mailserver postfix/smtpd[18495]: connect from unknown[192dot168dot69dot1]
Jan 3 14:31:21 mailserver postfix/smtpd[18495]: 29098B43A9: client=unknown[192dot168dot69dot1]
Jan 3 14:31:21 mailserver postfix/cleanup[18454]: 29098B43A9: message-id=<D148A6488B104F26B8DCED586170C606 * laptop>
Jan 3 14:31:21 mailserver postfix/qmgr[18226]: 29098B43A9: from=<nytridr*mydomain dot com>, size=10356, nrcpt=1 (queue active)
Jan 3 14:31:21 mailserver postfix/smtp[18498]: connect to tnknox01-smtp-01-public^uscc^com[165dot27dot240dot1]:25: No route to host
Jan 3 14:31:23 mailserver postfix/smtpd[18495]: disconnect from unknown[192dot168dot69dot1]

When I use thunderbird then everything goes through with out a problem

Jan 3 14:42:58 mailserver postfix/smtp[18801]: 76E6FB43A6: to=<my.wife*herwork.com>, relay=none, delay=1183, delays=1180/0.03/3.1/0, dsn=4.4.1, status=deferred (connect to wimidd01-smtp-01-public dot uscc dot com[165.27.244.1]:25: No route to host)
Jan 3 14:43:07 mailserver postfix/anvil[18708]: statistics: max connection rate 3/60s for (smtp:174.132.123.98) at Jan 3 14:39:46
Jan 3 14:43:07 mailserver postfix/anvil[18708]: statistics: max connection count 2 for (smtp space :174.dot132dot123dot98) at Jan 3 14:39:46
Jan 3 14:43:07 mailserver postfix/anvil[18708]: statistics: max cache size 1 at Jan 3 14:39:35

I think it has something to do with outlook and postfix, but for the life of me I can not figure it out.

Let me know what info you would like to see, but I do not think it is a configuration problem. Is there something I can add to make it were it would be more compatible with outlook?

Nyt

PS I had to get creative to post this.. I could not post any URL types in this post since I have not posted more then 15 post..:( ... hard to believe I never posted on here before even though I use this all the time.

* = @
^ / dot = .

[elija]

It looks like you are using Outlook on an IP that postfix isn't set up to relay for. Unfortunately, I can be no more help than that at the moment as I have never set up Postfix.

Yet...

[Nytridr]

everything is set up normally. have plain / tls / ssl all set up and through thunderbird i can connect and send mail with out any problems. i have it set for you have to log in before sending mail, which works with thnderbird but not with outlook. the only thing i can think off is that outlook is not communicating correctly with postfix. so any suggestions would be welcomed.