Thanks Gordon.

Please see below.

On Sat, 04 Apr 2009 20:09:04 -0700, Gordon Messmer <[email protected]>
wrote:
> Ricardo Kleemann wrote:
>>> What's connecting to Courier and starting the TLS session?
>>>
>> I believe it's msmtp, from one of my clients.
> 
> You can test various protocol settings with openssl's "s_client".  See 
> which of these work:
> 
> openssl s_client -starttls smtp -connect localhost:25 -ssl2
> openssl s_client -starttls smtp -connect localhost:25 -ssl3
> openssl s_client -starttls smtp -connect localhost:25 -tls1

$ openssl s_client -starttls smtp -connect localhost:25 -ssl2
CONNECTED(00000003)
write:errno=104

$ openssl s_client -starttls smtp -connect localhost:25 -ssl3
CONNECTED(00000003)
19951:error:14094410:SSL routines:SSL3_READ_BYTES:sslv3 alert handshake
failure:s3_pkt.c:1053:SSL alert number 40
19951:error:1409E0E5:SSL routines:SSL3_WRITE_BYTES:ssl handshake
failure:s3_pkt.c:530:

Using tls1 gives me errors of certificate expired, but at the same time I'd
like to understand why ssl2 and ssl3 are failing.

$ openssl s_client -starttls smtp -connect localhost:25 -tls1
CONNECTED(00000003)
depth=0 /C=US/ST=NY/L=New York/O=Courier Mail
Server/OU=Automatically-generated ESMTP STARTTLS
key/CN=localhost/[email protected]
verify error:num=18:self signed certificate
verify return:1
depth=0 /C=US/ST=NY/L=New York/O=Courier Mail
Server/OU=Automatically-generated ESMTP STARTTLS
key/CN=localhost/[email protected]
verify error:num=10:certificate has expired
notAfter=Dec 11 02:21:26 2004 GMT
verify return:1
depth=0 /C=US/ST=NY/L=New York/O=Courier Mail
Server/OU=Automatically-generated ESMTP STARTTLS
key/CN=localhost/[email protected]
notAfter=Dec 11 02:21:26 2004 GMT
verify return:1
---
Certificate chain
 0 s:/C=US/ST=NY/L=New York/O=Courier Mail
Server/OU=Automatically-generated ESMTP STARTTLS
key/CN=localhost/[email protected]
   i:/C=US/ST=NY/L=New York/O=Courier Mail
Server/OU=Automatically-generated ESMTP STARTTLS
key/CN=localhost/[email protected]
---
Server certificate
-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----
subject=/C=US/ST=NY/L=New York/O=Courier Mail
Server/OU=Automatically-generated ESMTP STARTTLS
key/CN=localhost/[email protected]
issuer=/C=US/ST=NY/L=New York/O=Courier Mail
Server/OU=Automatically-generated ESMTP STARTTLS
key/CN=localhost/[email protected]
---
No client certificate CA names sent
---
SSL handshake has read 1167 bytes and written 320 bytes
---
New, TLSv1/SSLv3, Cipher is AES256-SHA
Server public key is 1024 bit
Compression: zlib compression
Expansion: zlib compression
SSL-Session:
    Protocol  : TLSv1
    Cipher    : AES256-SHA
    Session-ID:
6AC48DDD3ED03429C4A1DAAEF7ECF74ADE9D7B17F78BDD7D90E0BF34E3FD73C3
    Session-ID-ctx:
    Master-Key:
92272CB5262B063D846E1A90CB48DEED4AAB68A862AF5E61EDF212B1ACB0656F282F05178B0C6597E729242984A4EE86
    Key-Arg   : None
   Compression: 1 (zlib compression)
    Start Time: 1238904625
    Timeout   : 7200 (sec)
    Verify return code: 10 (certificate has expired)
---
250 DSN

> 
> You should also check *all* of your configuration files for TLS_PROTOCOL 
> and TLS_STARTTLS_PROTOCOL.  Neither of those settings should have values 
> unless you understand what they do, and you have specific security 
> requirements:
> 
> grep ^TLS_PROTOCOL *
> grep ^TLS_STARTTLS_PROTOCOL *

I have commented out TLS_PROTOCOL in *all* of the files, and none have
TLS_STARTTLS_PROTOCOL

And yes, I restarted courier.

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