Question

I’ve been trying to use openssl to establish a connection with smtp.gmail.com port 587 or 465 with:
openssl s_client -host smtp.gmail.com -port 587 -starttls smtp

and the authentication, mail from, rcpt to, and data were all successful. but my problem is, after i write . in a new line, no 250 OK response from the server.

here is the process:

    CONNECTED(00000003)
    depth=1 /C=US/O=Google Inc/CN=Google Internet Authority
    verify error:num=20:unable to get local issuer certificate
    verify return:0
    ---
    Certificate chain
     0 s:/C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com
       i:/C=US/O=Google Inc/CN=Google Internet Authority
     1 s:/C=US/O=Google Inc/CN=Google Internet Authority
       i:/C=US/O=Equifax/OU=Equifax Secure Certificate Authority
    ---
    Server certificate
    -----BEGIN CERTIFICATE-----
    (certification)
    -----END CERTIFICATE-----
    subject=/C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com
    issuer=/C=US/O=Google Inc/CN=Google Internet Authority
    ---
    No client certificate CA names sent
    ---
    SSL handshake has read 1910 bytes and written 338 bytes
    ---
    New, TLSv1/SSLv3, Cipher is RC4-MD5
    Server public key is 1024 bit
    Secure Renegotiation IS supported
    Compression: NONE
    Expansion: NONE
    SSL-Session:
        Protocol  : TLSv1
        Cipher    : RC4-MD5
        Session-ID: 28E597C0025A93C82AD4A7C517F699B37D106D760597467B522C1041F1BC17C8
        Session-ID-ctx:
        Master-Key: 1CC83A8A4B7864DF9BBD9E9742B4E5A5937941EB2A28B88A1D4214920B77AC976D3ADC2DA7B60CF8BD6BC2B0712A42A2
        Key-Arg   : None
        Start Time: 1296911515
        Timeout   : 300 (sec)
        Verify return code: 20 (unable to get local issuer certificate)
    ---
    250 ENHANCEDSTATUSCODES
    ehlo
    250-mx.google.com at your service, [121.94.150.147]
    250-SIZE 35651584
    250-8BITMIME
    250-AUTH LOGIN PLAIN XOAUTH
    250 ENHANCEDSTATUSCODES
    auth login
    334 VXNlcm5hbWU6
    <my email>
    334 UGFzc3dvcmQ6
    <my password>
    235 2.7.0 Accepted
    mail from:<email>
    250 2.1.0 OK t14sm1471936icd.10
    rcpt to:<email>
    250 2.1.5 OK t14sm1471936icd.10
    data
    from: someone <email>
    354  Go ahead t14sm1471936icd.10
    to : someone <email>
    subject: test
    test
    test2
    .

451 4.4.2 Timeout - closing connection. t14sm1471936icd.10
read:errno=0

I am using cygwin in win7 32.

I’ve been searching for all of the possible keywords on google but no solution comes out.
PLEASE HELP!

Answer 1

Maybe add the ‘-crlf’ option to the comand line :

openssl s_client -host smtp.gmail.com -port 587 -starttls smtp -crlf