On 11/12/2013 9:03 PM, Viktor Dukhovni wrote:
On Wed, Dec 11, 2013 at 08:42:29PM +1100, Mark Jamsek wrote:

And, the glaringly obvious absence of SMTP auth mechanisms:

220 mail.bsdbox.co ESMTP Postfix
ehlo bsdbox.co
250-mail.bsdbox.co
250-STARTTLS
Only when not using TLS.
I'm not sure I understand what you mean here. I am using TLS, and
there is no SMTP authentication.
You're not "using" TLS in the above session.  The server supports
TLS, but "telnet host 25" does not *use* TLS.  To really use TLS
you need a client program that supports TLS.  I use "posttls-finger"
(because I wrote it to suit my needs).  You could make some progress
with "openssl s_client -starttls smtp -connect somehost:25", though
the latter shows less SMTP oriented output, you don't have to
compile it from source.

     $ posttls-finger "[mail.bsdbox.co]"
     posttls-finger: Connected to mail.bsdbox.co[110.146.148.136]:25
     posttls-finger: < 220 mail.bsdbox.co ESMTP Postfix
     posttls-finger: > EHLO amnesiac.example
     posttls-finger: < 250-mail.bsdbox.co
     posttls-finger: < 250-PIPELINING
     posttls-finger: < 250-SIZE 10240000
     posttls-finger: < 250-VRFY
     posttls-finger: < 250-ETRN
     posttls-finger: < 250-STARTTLS
     posttls-finger: < 250-ENHANCEDSTATUSCODES
     posttls-finger: < 250-8BITMIME
     posttls-finger: < 250 DSN
     posttls-finger: > STARTTLS
     posttls-finger: < 220 2.0.0 Ready to start TLS
     posttls-finger: mail.bsdbox.co[110.146.148.136]:25 Matched CommonName 
mail.bsdbox.co
     posttls-finger: certificate verification failed for 
mail.bsdbox.co[110.146.148.136]:25: self-signed certificate
     posttls-finger: mail.bsdbox.co[110.146.148.136]:25: 
subject_CN=mail.bsdbox.co, issuer_CN=mail.bsdbox.co, 
fingerprint=26:79:C0:78:CE:0E:DE:7C:83:6C:32:D4:4F:02:EF:72:51:2B:08:7A, 
pkey_fingerprint=80:B8:24:5B:EF:E4:B9:44:E9:EC:A6:40:0C:6A:6C:D7:9C:5E:B0:6F
     posttls-finger: Untrusted TLS connection established to 
mail.bsdbox.co[110.146.148.136]:25: TLSv1 with cipher DHE-RSA-AES256-SHA 
(256/256 bits)
     posttls-finger: > EHLO amnesiac.example
     posttls-finger: < 250-mail.bsdbox.co
     posttls-finger: < 250-PIPELINING
     posttls-finger: < 250-SIZE 10240000
     posttls-finger: < 250-VRFY
     posttls-finger: < 250-ETRN
     posttls-finger: < 250-AUTH PLAIN LOGIN
     posttls-finger: < 250-AUTH=PLAIN LOGIN
     posttls-finger: < 250-ENHANCEDSTATUSCODES
     posttls-finger: < 250-8BITMIME
     posttls-finger: < 250 DSN
     posttls-finger: > QUIT
     posttls-finger: < 221 2.0.0 Bye

It sure offers AUTH (PLAIN and LOGIN) to clients that use TLS.

On Wed, Dec 11, 2013 at 08:58:10PM +1100, Mark Jamsek wrote:

Wait. I think I understand what you're saying: my ISP perhaps blocks
my connections, so I need to use them as my $relayhost? Is it
possible to work around this somehow? I would rather not relay my
mail through my ISP.
Now you're beginning to see the light.  No you can't bypass the
ISP filter.  Either they are willing to turn the filter off for
you, or you need to relay through their submission service.

     http://www.postfix.org/SOHO_README.html
     http://www.postfix.org/SASL_README.html
     http://www.postfix.org/OVERVIEW.html
     http://www.postfix.org/BASIC_CONFIGURATION_README.html
     http://www.postfix.org/DEBUG_README.html
     http://www.postfix.org/QSHAPE_README.html

Thank you, sir! Using the $relayhost option to relay through my ISP has worked! I can't believe I didn't at least try that already. And, overlooking that I configured auth to only commence AFTER TLS, I foolishly expected auth mechanisms to be apparent using telnet (25). And thank you, again, for those links; I'll read them tonight and draft a letter to my ISP to request disabling the filter. Running your own mail server only to relay mail through a third party sort of defeats the purpose of running your own mail server.

n.b. Please forgive my elementary requests for help -- I am really really new to this. Thanks again, Viktor. Much appreciated, my friend. While I have your ear, do you know if Postfix developers take bitcoin donations? I'd love to contribute something to this great FOSS service.

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