Windows 8.1 Mail Client Sending via Postfix

Question

I have a postfix server setup to accept outgoing mail from STMP authenticated clients. It has been working this way for many years with success for a large number of different e-mail clients. Recently, I got a Windows 8.1 based tablet computer and would like to use the Metro UI mail app that came with it. The IMAP client functionality of this app seems to work great, but I'm having difficulty getting it to send e-mail successfully. Mail submission takes place over SSL on TCP port 465.

I found some commentary on the web that perhaps some recent MS clients are picky about having LOGIN available as a SASL authenticaiton typs, so I enabled that, but no significant improvement.

Digging a little deeper, I enabled debug logging for the IP address that is attempting to send and extracted the following transcript from the logs:

> unknown[ip.add.re.ss]: 220 mail.my.domian ESMTP Postfix Mail Deamon
< unknown[ip.add.re.ss]: EHLO WINMJGRJQ83FFQ
> unknown[ip.add.re.ss]: 250-mail.my.domain
> unknown[ip.add.re.ss]: 250-PIPELINING
> unknown[ip.add.re.ss]: 250-SIZE 42428800
> unknown[ip.add.re.ss]: 250-ETRN
> unknown[ip.add.re.ss]: 250-AUTH PLAIN LOGIN
> unknown[ip.add.re.ss]: 250-AUTH=PLAIN LOGIN
> unknown[ip.add.re.ss]: 250-ENHANCEDSTATUSCODES
> unknown[ip.add.re.ss]: 250-8BITMIME
> unknown[ip.add.re.ss]: 250 DSN
< unknown[ip.add.re.ss]: AUTH LOGIN
> unknown[ip.add.re.ss]: 334 VXNlcm5hbWU6
< unknown[ip.add.re.ss]: --REDACTED--Base64Username
> unknown[ip.add.re.ss]: 334 UGFzc3dvcmQ6
< unknown[ip.add.re.ss]: --REDACTED--Base64Password
> unknown[ip.add.re.ss]: 235 2.7.0 Authentication successful
< unknown[ip.add.re.ss]: QUIT
> unknown[ip.add.re.ss]: 221 2.0.0 Bye

I'm fairly stumped at this point. I think that I can rule out SSL problems since the client has connected successfully and started the STMP session. It looks like the client and server have been able to agree on an authentication method and have in fact completed authenticaion successfully. The only thing remaining is why the Windows 8.1 mail client decided to respond to Authenticaiton successful with QUIT rather than MAIL FROM: like I would expect.

I got an issue like that in the past, was an antivirus on the client computer with a firewall that was dropping my SMTP traffic. Easy to test out. — yagmoth555, Jan 09 '15 at 19:11
After a little more experimentation I found the windows mail client has trouble with the account once it fails. Despite many attempts to reconfigure the account, including putting the tablet on the local network of the SMTP server (there is will accept unauthenticated mail for relay from local clients on port 25) with no authentication and no SSL it still had the same behavior of sending a quit instead of a mail from. I deleted the account from the mail app and set it up again (full up with authentication and SSL on port 465) and it worked out fine the first time. — Adam Bumpus, Jan 11 '15 at 14:53

score 1 · Answer 1 · edited Apr 13 '17 at 12:13

_{convert comment to CW}

After a little more experimentation I found the windows mail client has trouble with the account once it fails.

Despite many attempts to reconfigure the account with no authentication and no SSL, it still had the same behavior of sending a quit instead of a mail from. I also have tried to put the tablet on the local network of the SMTP server (this will accept unauthenticated mail for relay from local clients on port 25).

I deleted the account from the mail app and set it up again (full up with authentication and SSL on port 465) and it worked out fine the first time.

Windows 8.1 Mail Client Sending via Postfix

1 Answers1