Windows 10 Mail authenticating improperly
Question asked by Gene Salvatore - December 5, 2016 at 4:00 PM
Unanswered
We have a client that wishes to use the Mail program built into Windows10 to capture mail from our SM 15.x server. The email account is setup as an IMAP account and we have validated they are correct both through a GoTo Assist session, and by testing the admin account for the domain on a local PC here.
 
While an account can login and download IMAP messages and folders, the account(s) cannot send.
 
In looking through the SMTP logs we can see why - the Mail program is trying to authenticate as if it's in a MS domain environment: Authenticating as domainname.com\admin@domainname.com
 
Has anyone run across this before, and have any solutions? 
 
Note: Autodiscovery is not setup for this domain and following the steps in the KB https://portal.smartertools.com/kb/a2804/windows-mail-and-smartermail.aspx produce the same results.
 
[2016.12.05] 17:29:00 [96.39.87.245][55905592] rsp: 220 mail.domainname.com | SmarterMail Enterprise
[2016.12.05] 17:29:00 [96.39.87.245][55905592] connected at 12/5/2016 5:29:00 PM
[2016.12.05] 17:29:00 [96.39.87.245][55905592] cmd: EHLO [IPv6:::ffff:10.1.0.141]
[2016.12.05] 17:29:00 [96.39.87.245][55905592] rsp: 250-mail.domainname.com Hello [96.39.87.245]250-SIZE 52428800250-AUTH LOGIN CRAM-MD5250-STARTTLS250-8BITMIME250 OK
[2016.12.05] 17:29:00 [96.39.87.245][55905592] cmd: STARTTLS
[2016.12.05] 17:29:00 [96.39.87.245][55905592] rsp: 220 Start TLS negotiation
[2016.12.05] 17:29:00 [96.39.87.245][55905592] cmd: EHLO [IPv6:::ffff:10.1.0.141]
[2016.12.05] 17:29:00 [96.39.87.245][55905592] rsp: 250-mail.domainname.com Hello [96.39.87.245]250-SIZE 52428800250-AUTH LOGIN CRAM-MD5250-8BITMIME250 OK
[2016.12.05] 17:29:00 [96.39.87.245][55905592] cmd: AUTH LOGIN
[2016.12.05] 17:29:00 [96.39.87.245][55905592] rsp: 334 VXNlcm5hbWU6
[2016.12.05] 17:29:00 [96.39.87.245][55905592] Authenticating as domainname.com\admin@domainname.com
[2016.12.05] 17:29:00 [96.39.87.245][55905592] rsp: 334 UGFzc3dvcmQ6
[2016.12.05] 17:29:01 [96.39.87.245][55905592] rsp: 535 Authentication failed
[2016.12.05] 17:29:01 [96.39.87.245][55905592] disconnected at 12/5/2016 5:29:01 PM
 

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As you said, the problem is here: [2016.12.05] 17:29:00 [96.39.87.245][55905592] Authenticating as domainname.com\admin@domainname.com
 
Try:
Go to Account Settings > and uncheck "Use the same username and password for sending email"
Then, fill the fields bellow with the valid username (acccount@domain.tld) and password. Then save all again.
 
Try to send the email now and check again the log to view the authentication:
[2016.12.05] 17:29:00 [96.39.87.245][55905592] Authenticating as domainname.com\admin@domainname.com
1
Another example of a large corporation doing everything they can to force users into their environment for monetarization purposes.

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