Author Topic: e-mail: SMTP AUTH + SSL/TLS  (Read 1964 times)

alioth

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e-mail: SMTP AUTH + SSL/TLS
« on: February 26, 2004, 12:20:27 pm »
I recently purchased an SL-5600 and a Symbol LA-4137 Wi-Fi card.
One of my goals is to have secure e-mail even when connected through a
Wi-Fi access point over which I have no control.  This means finding
an e-mail provider that supports SMTP and POP3 or IMAP service over
encrypted SSL/TLS channels.

  I started experimentation with smtpauth.earthlink.net, on which my
ISP provides STARTTLS service.  Even after upgrading to the 1.32 Sharp
ROM, I was never able to send a message through this server because
the Zaurus mailer could not login using the SMTP AUTH protocol.  Not
knowing the cause of the problem, I searched for other providers of
secure e-mail and found www.tuffmail.com.  Authentication initially
failed on Tuffmail, but, working with support@tuffmail.com, I believe
that we have found the problem:

    The Zaurus mailer gets confused and does not attempt to authenticate
    if the SMTP \"220\" greeting contains continuation lines.

For example, smtpauth.earthlink.net emits three lines

  $ telnet smtpauth.earthlink.net 25
  220-stork.mail.pas.earthlink.net ESMTP Exim 3.33 #1 Thu, 26 Feb 2004      08:45:36 -0800
  220-NO UCE.  EarthLink does not authorize the use of its computers or      network  
  220 equipment to deliver, accept, transmit, or distribute unsolicited e-mail.

Support@tuffmail.com kindly changed its SMTP greeting to only emit one line:

  $ telnet smtp.mxes.net 587
  220 smtp.mxes.net ESMTP Postfix

to avoid the limitations of the Zaurus mailer.

  I now have secure Zaurus e-mail working through a free trial account
on Tuffmail.  I start stunnel proxies to provide SSL connections
between the Zaurus and the Tuffmail servers:
 
  /usr/sbin/stunnel -P none -c -d 10025 -r smtp.mxes.net:465 # SMTP
  /usr/sbin/stunnel -P none -c -d 10110 -r mail.mxes.net:995 # POP3
  /usr/sbin/stunnel -P none -c -d 10143 -r mail.mxes.net:993 # IMAP

and configure the Zaurus mailer to use localhost as its server and
port 10025 for SMTP, 10110 for POP3, and 10143 for IMAP.