Hello all,
Trying to connect to an Exchange 2003 SP2 Virtual SMTP Server with
s_client but get the following (OpenSSL 0.9.8g):
openssl s_client -connect mail.somehost.com:587 -state
CONNECTED(00000003)
SSL_connect:before/connect initialization
SSL_connect:SSLv2/v3 write client hello A
SSL_connect:error in SSLv2/v3 read server hello A
1520:error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown
protocol:s23_clnt.c:583:
openssl s_client -connect mail.somehost.com:587 -state -ssl2
CONNECTED(00000003)
SSL_connect:before/connect initialization
SSL_connect:SSLv2 write client hello A
(cursor waiting)
openssl s_client -connect mail.somehost.com:587 -state -ssl3
CONNECTED(00000003)
SSL_connect:before/connect initialization
SSL_connect:SSLv3 write client hello A
SSL3 alert write:fatal:handshake failure
SSL_connect:error in SSLv3 read server hello A
1694:error:1408F10B:SSL routines:SSL3_GET_RECORD:wrong version
number:s3_pkt.c:284:
openssl s_client -connect mail.somehost.com:587 -state -starttls smtp
CONNECTED(00000003)
SSL_connect:before/connect initialization
SSL_connect:SSLv2/v3 write client hello A
SSL_connect:SSLv3 read server hello A
***certificate ***
...
SSL handshake has read 1022 bytes and written 335 bytes
---
New, TLSv1/SSLv3, Cipher is RC4-MD5
Server public key is 1024 bit
Compression: NONE
Expansion: NONE
SSL-Session:
Protocol : TLSv1
Cipher : RC4-MD5
Session-ID: xxxxx ...
Session-ID-ctx:
Master-Key: xxxxx ...
Key-Arg : None
Start Time: 1247280228
Timeout : 300 (sec)
Verify return code: 21 (unable to verify the first certificate)
The certificate on the Exchange Server was self-signed and was created
through the IIS SelfCert tool. I thought perhaps the certificate
wasn't trusted but it seems to be failing at the handshake phase; I
double-checked by trying out Google's mail server (smtp.gmail.com)
which supports SSL/TLS and while the certificate says it's untrusted,
I still get a 250 OK, so I'm not thinking it's the certificate.
Tried it on another box running 0.9.8a, same results. I'm definitely
not ruling out a poorly-configured Exchange box -- I've gone through
dozens of technet and web articles and everything *should* be working,
but clearly it's not.
Any ideas? I've been banging away at this for the last couple days
and am at wit's end... any help greatly appreciated.
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