Mail.app 3.1 +Exchange 2003 OWA

[tgarci01]

Just converting over to a Mac for my work laptop. I am having a heck of a time getting Mail to work with an Exchange 2003 setup. Previously my work laptop was a R60 running SUSE 10.3 and Evolution as the email client. This worked fine with our mail server as does my AT&T Tilt, several iPhones, etc..

 

With Mail I can sync fine on receive in either Mail's IMAP or Exchange setups. My problem is hitting the server on the SMTP side and (of course) sending mail... I've tried with and without SSL on port 465 which is what the IT guys have it set for. I've done the PASSWORD and NTLM authentication with and without my DOMAIN\ in front of my user name... NADA...

 

I know that some threads elsewhere say that Mail automatically appends /Exchange/user_name on the server string versus /owa/user_name

 

 

In Mail Connection Doctor I get the "Could not connect to this SMTP server" regardless of playing with URLs/SSL/etc... In the detail, I get this....

 

 

CONNECTED Feb 09 15:25:42.537 [kCFStreamSocketSecurityLevelNone]  -- host:webmail.intralot.us -- port:465 -- socket:0x10ca1400 -- thread:0x7c7250

READ Feb 09 15:25:42.685 [kCFStreamSocketSecurityLevelNone]  -- host:webmail.intralot.us -- port:465 -- socket:0x10ca1400 -- thread:0x7c7250
220 webmail.intralot.us Microsoft ESMTP MAIL Service, Version: 6.0.3790.3959 ready at  Sat, 9 Feb 2008 13:25:57 -0700 

WROTE Feb 09 15:25:42.817 [kCFStreamSocketSecurityLevelNone]  -- host:webmail.intralot.us -- port:465 -- socket:0x10ca1400 -- thread:0x7c7250
EHLO [172.29.8.207]

READ Feb 09 15:25:42.969 [kCFStreamSocketSecurityLevelNone]  -- host:webmail.intralot.us -- port:465 -- socket:0x10ca1400 -- thread:0x7c7250
250-webmail.intralot.us Hello [65.12.161.5]
250-TURN
250-SIZE 20480000
250-ETRN
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-VRFY
250-TLS
250-STARTTLS
250-X-EXPS GSSAPI NTLM LOGIN
250-X-EXPS=LOGIN
250-AUTH GSSAPI NTLM LOGIN
250-AUTH=LOGIN
250-X-LINK2STATE
250-XEXCH50
250 OK

WROTE Feb 09 15:25:42.997 [kCFStreamSocketSecurityLevelNone]  -- host:webmail.intralot.us -- port:465 -- socket:0x10ca1400 -- thread:0x7c7250
STARTTLS

READ Feb 09 15:25:43.146 [kCFStreamSocketSecurityLevelNone]  -- host:webmail.intralot.us -- port:465 -- socket:0x10ca1400 -- thread:0x7c7250
220 2.0.0 SMTP server ready

WROTE Feb 09 15:25:43.777 [kCFStreamSocketSecurityLevelNone]  -- host:webmail.intralot.us -- port:465 -- socket:0x10ca1400 -- thread:0x7c7250
EHLO [172.29.8.207]

READ Feb 09 15:25:43.932 [kCFStreamSocketSecurityLevelNone]  -- host:webmail.intralot.us -- port:465 -- socket:0x10ca1400 -- thread:0x7c7250
250-webmail.intralot.us Hello [65.12.161.5]
250-TURN
250-SIZE 20480000
250-ETRN
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-VRFY
250-X-EXPS GSSAPI NTLM LOGIN
250-X-EXPS=LOGIN
250-AUTH GSSAPI NTLM LOGIN
250-AUTH=LOGIN
250-X-LINK2STATE
250-XEXCH50
250 OK

 

 

For some reason I think I am getting to the server and authenticating OK...its just failing beyond that point...

 

I'm hoping one of you GURUs can figure this out or point me in the right direction. This is the only thing that is currently still tying me to my Linux box....

 

Thanks!