Re: Problems sending mail with ssl on port 465

[Torben Knudsen]

I now tried a lot of what both you and Hasse Hagen Johansen suggested.

I have not really success but all the errors and information I found
useful is below.  Do you have more help for me?  Thanks for your time
so far.  

>From *Message* when using 465 and sending on port 587 with starttls
and gnutls-cli installed and without vpn

Opening STARTTLS connection to `smtp.es.aau.dk:465'

Then gnus hangs and I have to use C-g twice to get control back

---------

>From the command line test with gnutls-cli 
 
tk@tk-laptop:~$ gnutls-cli --port 465 smtp.es.aau.dk
Resolving 'smtp.es.aau.dk'...
Connecting to '130.225.51.26:465'...
- Certificate type: X.509
 - Got a certificate list of 1 certificates.
 - Certificate[0] info:
  - subject `C=DK,ST=Denmark,O=Aalborg Universitet,OU=SMTP 
server,CN=smtp.es.aau.dk', issuer `O=Aalborg Universitet,OU=Institut for 
Elektroniske Systemer,EMAIL=iesca@ies.aau.dk,L=Aalborg,ST=Denmark,C=DK,CN=AAU 
IES CA', RSA key 1024 bits, signed using RSA-SHA, activated `2009-06-15 
07:30:23 UTC', expires `2012-06-14 07:30:23 UTC', SHA-1 fingerprint 
`bbc9274ddd7d193dcd1fa8585bbb4490ba020fcc'
- The hostname in the certificate matches 'smtp.es.aau.dk'.
- Peer's certificate issuer is unknown
- Peer's certificate is NOT trusted
- Version: TLS1.0
- Key Exchange: RSA
- Cipher: AES-128-CBC
- MAC: SHA1
- Compression: NULL
- Handshake was completed

- Simple Client Mode:

220 mta1.es.aau.dk ESMTP Exim 4.63 Tue, 15 Jun 2010 07:49:20 +0200
QUIT
221 mta1.es.aau.dk closing connection
- Peer has closed the GNUTLS connection
tk@tk-laptop:~$ 

----------

Trace from sending on port 587 with starttls and gnutls-cli installed
and without vpn
Notice the "535 Incorrect authentication data"

Process SMTP killed
220 mta1.es.aau.dk ESMTP Exim 4.63 Tue, 15 Jun 2010 07:53:45 +0200
EHLO tk-laptop
250-mta1.es.aau.dk Hello tk-nb.office.es.aau.dk [172.26.10.148]
250-SIZE 52428800
250-PIPELINING
250-STARTTLS
250 HELP
STARTTLS
220 TLS go ahead
EHLO tk-laptop
250-mta1.es.aau.dk Hello tk-nb.office.es.aau.dk [172.26.10.148]
250-SIZE 52428800
250-PIPELINING
250-AUTH PLAIN LOGIN
250 HELP
AUTH PLAIN AHRrQGVzLmFhdS5kawAxdGtqcmFwMg==
535 Incorrect authentication data
QUIT
221 mta1.es.aau.dk closing connection

-------------

Trace when starttls and gnutls-cli is NOT installed but a vpn
connection is active.
Notice that no authentication seems to go on 

Process SMTP deleted
220 mta1.es.aau.dk ESMTP Exim 4.63 Tue, 15 Jun 2010 08:12:21 +0200
EHLO tk-laptop
250-mta1.es.aau.dk Hello pc1.vpn.control.aau.dk [172.16.14.1]
250-SIZE 52428800
250-PIPELINING
250-STARTTLS
250 HELP
MAIL FROM:<tk@es.aau.dk> SIZE=603
250 OK
RCPT TO:<tk@es.aau.dk>
250 Accepted
DATA
354 Enter message, ending with "." on a line by itself
From: Torben Knudsen <tk@es.aau.dk>
To: Torben Knudsen <tk@es.aau.dk>
Subject: dd
Date: Tue, 15 Jun 2010 08:12:18 +0200
Message-ID: <87vd9k4yf1.fsf@es.aau.dk>
User-Agent: Gnus/5.13 (Gnus v5.13) Emacs/23.1 (gnu/linux)
MIME-Version: 1.0
Content-Type: text/plain; charset=iso-8859-1
Content-Transfer-Encoding: quoted-printable


--=20
Associate Prof. Ph.D Torben Knudsen     Mobile  : (+45) 2787 9826
Section of Automation and Control,      Direct  : 6 8694
Department of Electronic Systems,       Email   : tk@es.aau.dk=20=20=20
Aalborg University=20
Fredrik Bajersvej 7=20
DK-9220 Aalborg =D8
Denmark=20
.
250 OK id=1OOPNr-0001af-8Q
QUIT
221 mta1.es.aau.dk closing connection

-- 
Associate Prof. Ph.D Torben Knudsen     Mobile  : (+45) 2787 9826
Section of Automation and Control,      Direct  : 6 8694
Department of Electronic Systems,       Email   : tk@es.aau.dk