On Thu, Jan 28, 2021 at 08:18:05PM +0000, Chu, Uy wrote:

> I am having trouble with one of our application server not being able
> to connect to send emails.  I noticed the issue of connection lost
> after STARTTLS.  Is it a configuration on the SMTP server or the
> application?
> 
> Jan 28 10:19:04 mailgate15 postfix/smtpd[10717]: setting up TLS connection 
> from crowd-prod02.slac.stanford.edu[134.79.98.190]
> Jan 28 10:19:04 mailgate15 postfix/smtpd[10717]: 
> crowd-prod02.slac.stanford.edu[134.79.98.190]:
>   TLS cipher list
>      kEECDH +kEECDH+SHA
>      kEDH +kEDH+SHA +kEDH+CAMELLIA
>      kECDH +kECDH+SHA
>      kRSA +kRSA+SHA +kRSA+CAMELLIA
>      !aNULL !eNULL !SSLv2 !RC4 !MD5 !DES !EXP !SEED !IDEA !3DES
>      !EXP !MEDIUM !LOW
>      !DES !3DES !SSLv2 !RC4
>      !aNULL

Reformatting your cipher list, it is obvious that someone who doesn't
exactly know what they're doing has customised the cipher list, in
ways I would not recommend, *but* not to the point where I'd expect
to see interoperability issues for most clients.

> Jan 28 10:19:04 mailgate15 postfix/smtpd[10717]: SSL_accept error from 
> crowd-prod02.slac.stanford.edu[134.79.98.190]: 0
> Jan 28 10:19:04 mailgate15 postfix/smtpd[10717]: lost connection after 
> STARTTLS from crowd-prod02.slac.stanford.edu[134.79.98.190]

So the above is not sufficient to identity the problem completing the
TLS handshake.  As noted by Wietse, configuration data would be best.

FWIW, connections from "posttls-finger" appear to work:

  $ posttls-finger -c -lmay "[mailgate15.slac.stanford.edu]"
    posttls-finger: mailgate15.slac.stanford.edu[134.79.102.21]:25:
        subject_CN=smtpout.slac.stanford.edu, issuer_CN=InCommon ECC Server CA,
        
fingerprint=B9:76:16:F3:63:08:EA:5D:2A:02:6A:B3:5D:2C:46:01:5F:36:13:52:03:8B:23:54:07:83:E3:72:80:C3:3F:14,
        
pkey_fingerprint=52:9D:09:15:67:89:1F:4D:6B:04:B4:D9:BF:27:62:2C:02:59:BC:99:40:4F:E4:A0:14:E6:3F:38:ED:B9:33:03
        posttls-finger: Untrusted TLS connection established to
        mailgate15.slac.stanford.edu[134.79.102.21]:25: TLSv1.2 with cipher
        ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)

Is the client configured to authenticate the server?  The server
certificate chains appears to be missing the intermediate CA, or to be
directly signed by a root CA that's not in the usual trusted CA
bundles...

 0 subject: /C=US/postalCode=94305/ST=California/L=Stanford/street=450 Jane 
Stanford Way/O=Stanford University/OU=SLAC/CN=smtpout.slac.stanford.edu
    issuer: /C=US/ST=MI/L=Ann Arbor/O=Internet2/OU=InCommon/CN=InCommon ECC 
Server CA
   cert 
digest=B9:76:16:F3:63:08:EA:5D:2A:02:6A:B3:5D:2C:46:01:5F:36:13:52:03:8B:23:54:07:83:E3:72:80:C3:3F:14
   pkey 
digest=52:9D:09:15:67:89:1F:4D:6B:04:B4:D9:BF:27:62:2C:02:59:BC:99:40:4F:E4:A0:14:E6:3F:38:ED:B9:33:03
Certificate:
    Data:
        Version: 3 (0x2)
        Serial Number:
            04:f6:2c:5e:21:7e:bc:37:23:02:38:9d:10:8d:64:49
        Signature Algorithm: ecdsa-with-SHA256
        Issuer: C = US, ST = MI, L = Ann Arbor, O = Internet2, OU = InCommon, 
CN = InCommon ECC Server CA
        Validity
            Not Before: Oct  1 00:00:00 2020 GMT
            Not After : Oct  1 23:59:59 2021 GMT
        Subject: C = US, postalCode = 94305, ST = California, L = Stanford, 
street = 450 Jane Stanford Way, O = Stanford University, OU = SLAC, CN = 
smtpout.slac.stanford.edu
        Subject Public Key Info:
            Public Key Algorithm: rsaEncryption
                RSA Public-Key: (2048 bit)
                Modulus:
                    00:dc:7b:cc:82:61:27:1d:d0:3e:6b:ff:8e:e4:96:
                    00:91:07:c5:f8:71:8e:fa:14:ff:c5:d7:1b:28:bf:
                    dd:ed:50:7a:69:a7:fb:fa:b8:40:bb:7d:65:6d:4d:
                    a7:66:e7:ca:ae:e8:8a:3d:ef:28:a2:00:10:02:d4:
                    2d:20:cc:fd:2d:9f:47:25:d7:30:8b:de:40:b5:af:
                    fc:00:2e:a8:c1:d0:4e:19:9c:71:13:11:c6:e7:18:
                    a9:b2:43:93:a2:be:f9:1c:be:ea:ae:86:a0:9b:b5:
                    64:c4:bc:9a:c4:26:15:95:42:8a:f8:0e:f0:9d:e6:
                    f2:dc:57:ca:cc:fe:59:25:27:b0:a2:19:73:e1:90:
                    60:7c:bd:32:d6:36:cb:49:9a:d3:cc:ec:43:58:1a:
                    c7:8f:c0:23:f1:3d:ea:fb:92:9f:82:e9:35:68:f8:
                    54:4f:4c:21:db:27:58:0c:99:21:4e:79:ce:b0:6f:
                    e0:4a:8e:5c:29:92:18:0f:68:38:e1:22:f6:d3:97:
                    66:f9:0d:80:b2:2c:50:4d:bc:d7:50:2c:38:b3:39:
                    77:00:e9:2e:b3:42:fd:ce:85:59:30:35:c4:43:b4:
                    00:bd:14:a2:e6:19:36:bd:9f:24:4b:83:b5:5a:af:
                    bc:47:be:69:15:1d:c5:b5:5e:d6:30:76:73:f8:46:
                    98:79
                Exponent: 65537 (0x10001)
        X509v3 extensions:
            X509v3 Authority Key Identifier: 
                
keyid:E4:B7:CF:CB:0A:94:74:A7:9C:AD:A8:12:04:3A:D0:29:5D:2E:FC:EE

            X509v3 Subject Key Identifier: 
                A7:C1:08:7E:76:0D:D4:B6:61:1E:7A:2C:74:99:C6:8B:4F:B7:88:15
            X509v3 Key Usage: critical
                Digital Signature
            X509v3 Basic Constraints: critical
                CA:FALSE
            X509v3 Extended Key Usage: 
                TLS Web Server Authentication, TLS Web Client Authentication
            X509v3 Certificate Policies: 
                Policy: 1.3.6.1.4.1.5923.1.4.3.1.1
                  CPS: https://www.incommon.org/cert/repository/cps_ssl.pdf
                Policy: 2.23.140.1.2.2

            X509v3 CRL Distribution Points: 

                Full Name:
                  URI:http://crl.incommon-ecc.org/InCommonECCServerCA.crl

            Authority Information Access: 
                CA Issuers - 
URI:http://cert.incommon-ecc.org/InCommonECCServerCA.crt
                OCSP - URI:http://ocsp.incommon-ecc.org

            CT Precertificate SCTs: 
                Signed Certificate Timestamp:
                    Version   : v1 (0x0)
                    Log ID    : 7D:3E:F2:F8:8F:FF:88:55:68:24:C2:C0:CA:9E:52:89:
                                79:2B:C5:0E:78:09:7F:2E:6A:97:68:99:7E:22:F0:D7
                    Timestamp : Oct  1 22:01:54.987 2020 GMT
                    Extensions: none
                    Signature : ecdsa-with-SHA256
                                30:45:02:20:63:5E:03:D5:47:95:37:8D:5D:70:B0:76:
                                0F:59:A1:9A:41:32:64:3F:EA:D0:82:E4:04:B4:B5:8A:
                                04:83:B4:2E:02:21:00:EB:72:C8:AD:20:D5:AE:66:61:
                                C6:94:B1:36:42:00:22:11:65:BE:2D:8C:0B:25:93:01:
                                A2:D9:FB:DA:38:99:0B
                Signed Certificate Timestamp:
                    Version   : v1 (0x0)
                    Log ID    : 94:20:BC:1E:8E:D5:8D:6C:88:73:1F:82:8B:22:2C:0D:
                                D1:DA:4D:5E:6C:4F:94:3D:61:DB:4E:2F:58:4D:A2:C2
                    Timestamp : Oct  1 22:01:55.311 2020 GMT
                    Extensions: none
                    Signature : ecdsa-with-SHA256
                                30:46:02:21:00:8E:4A:77:BF:2F:33:7C:D4:ED:9D:A5:
                                70:C2:6B:C0:88:68:6A:61:E7:91:01:EF:22:9B:E2:99:
                                C6:2C:4B:E7:04:02:21:00:F0:BA:AF:FD:97:64:F3:98:
                                4F:10:D3:8E:68:32:3A:46:A3:A4:44:F1:59:EC:4C:7C:
                                29:EF:51:C7:97:90:92:DF
            X509v3 Subject Alternative Name: 
                DNS:smtpout.slac.stanford.edu, 
DNS:mailgate15.slac.stanford.edu, DNS:mailgate16.slac.stanford.edu, 
DNS:mailgate17.slac.stanford.edu
    Signature Algorithm: ecdsa-with-SHA256
         30:45:02:21:00:93:62:b2:c4:fe:39:5c:61:55:11:a3:db:d4:
         ae:02:24:a1:cc:48:1f:d2:04:34:8a:8d:cb:96:79:12:4f:73:
         02:02:20:3e:83:0d:1f:d6:8c:c6:b4:e9:cc:21:ce:c2:1c:15:
         82:95:c1:6f:ed:87:d9:2d:aa:0e:fc:77:b5:9e:e0:1f:1f
-----BEGIN CERTIFICATE-----
MIIGLTCCBdOgAwIBAgIQBPYsXiF+vDcjAjidEI1kSTAKBggqhkjOPQQDAjB2MQsw
CQYDVQQGEwJVUzELMAkGA1UECBMCTUkxEjAQBgNVBAcTCUFubiBBcmJvcjESMBAG
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Hw==
-----END CERTIFICATE-----

-- 
    Viktor.

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