New Old Stk wrote:
I tried both Thunderbird and Outlook 2007. SMTP port in both was set to 25. I experimented with all combinations of SSL/TLS settings available in TB and Outlook as well. Thunderbird though displayed the following message (TLS/25):

    Sending of message failed. An error occured sending mail: Unable to
    connect to SMTP server one.mailexpeditor.com
    <http://one.mailexpeditor.com> via STARTTLS since it doesn't offer
    STARTTLS In EHLO response.

Server's maillog responded with even less information:
    Jul  8 15:15:43 one postfix/smtpd[11248]: connect from
    host86-171-60-46.range86-171.btcentralplus.com
    <http://host86-171-60-46.range86-171.btcentralplus.com>[86.171.60.46]

    Jul  8 15:15:43 one postfix/smtpd[11248]: disconnect from
    host86-171-60-46.range86-171.btcentralplus.com
    <http://host86-171-60-46.range86-171.btcentralplus.com>[86.171.60.46]

I also uncommented smtps and three following lines in master.cf <http://master.cf>, reloaded postfix but still no go.
    smtps     inet  n       -       n       -       -       smtpd
      -o smtpd_tls_wrappermode=yes
      -o smtpd_sasl_auth_enable=yes
      -o smtpd_client_restrictions=permit_sasl_authenticated,reject

After trying Outlook with SSL/25, server logged:
    Jul  8 15:19:00 one postfix/smtpd[11248]: connect from
    host86-171-60-46.range86-171.btcentralplus.com
    <http://host86-171-60-46.range86-171.btcentralplus.com>[86.171.60.46]
    Jul  8 15:19:00 one postfix/smtpd[11248]: lost connection after
    UNKNOWN from host86-171-60-46.range86-171.btcentralplus.com
    <http://host86-171-60-46.range86-171.btcentralplus.com>[86.171.60.46]
    Jul  8 15:19:00 one postfix/smtpd[11248]: disconnect from
    host86-171-60-46.range86-171.btcentralplus.com
    <http://host86-171-60-46.range86-171.btcentralplus.com>[86.171.60.46]

Many thanks George On Wed, Jul 8, 2009 at 2:52 PM, Brian Evans - Postfix List <[email protected] <mailto:[email protected]>> wrote:
    New Old Stk wrote:
>
     >
     > Sorry Brian, i didn't post the full command I was testing the
     > connection with. Yes, it had -starttls among other things and it did
     > work fine. I was able to connect, AUTH PLAIN generated string (below)
     > and get 235 2.0.0 Authentication successful:
     >
     >     #perl -MMIME::Base64 -e 'print
    encode_base64("\0username\0password")'
     >     /AHVzZXJuYW1lAlXXXX&YYYYZZZZ/
     >     #openssl s_client -starttls smtp -crlf -connect localhost:25
     >
> 8. If I set mail client to authenticate and use SSL result in log is
     > as follows:
     >
     >
> Jun 30 16:47:16 one postfix/smtpd[23346]: connect from > host86-165-212-234.range86-165.btcentralplus.com
    <http://host86-165-212-234.range86-165.btcentralplus.com/>
     >     <http://host86-165-212-234.range86-165.btcentralplus.com
    <http://host86-165-212-234.range86-165.btcentralplus.com/>>[86.165.212.234]
> Jun 30 16:47:16 one postfix/smtpd[23346]: lost connection after > UNKNOWN from host86-165-212-234.range86-165.btcentralplus.com
    <http://host86-165-212-234.range86-165.btcentralplus.com/>
> <http://host86-165-212-234.range86-165.btcentralplus.com
    <http://host86-165-212-234.range86-165.btcentralplus.com/>>[86.165.212.234]

> Jun 30 16:47:16 one postfix/smtpd[23346]: disconnect from > host86-165-212-234.range86-165.btcentralplus.com
    <http://host86-165-212-234.range86-165.btcentralplus.com/>
     >     <http://host86-165-212-234.range86-165.btcentralplus.com
    <http://host86-165-212-234.range86-165.btcentralplus.com/>>[86.165.212.234]
     >
Some clients use "SSL" to mean the archaic smtps protocol (most
    famously
    Outlook and Outlook Express) on port 465.
If you uncomment the smtps line in master.cf <http://master.cf/>,
    you may see a difference.
Most modern clients, such as Squirelmail and Thunderbird, use STARTTLS
    as one of their options when sending email.
Brian


Try 'openssl s_client ...' from the same machine you're using thunderbird on. Maybe some firewall/router is interfering with TLS.

If it's windows, google "openssl for windows"

You might have better luck using the "submission" port 587 rather than 25.

  -- Noel Jones

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