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No Format
openssl s_client -starttls smtp -connect smtp.gmail.com:587 -crlf
 
CONNECTED(00000003)
depth=2 C = US, O = GeoTrust Inc., CN = GeoTrust Global CA
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 G2
 1 s:/C=US/O=Google Inc/CN=Google Internet Authority G2
   i:/C=US/O=GeoTrust Inc./CN=GeoTrust Global CA
 2 s:/C=US/O=GeoTrust Inc./CN=GeoTrust Global CA
   i:/C=US/O=Equifax/OU=Equifax Secure Certificate Authority
---
Server certificate
-----BEGIN CERTIFICATE-----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-----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 G2
---
No client certificate CA names sent
---
SSL handshake has read 3990 bytes and written 466 bytes
---
New, TLSv1/SSLv3, Cipher is ECDHE-RSA-AES128-GCM-SHA256
Server public key is 2048 bit
Secure Renegotiation IS supported
Compression: NONE
Expansion: NONE
SSL-Session:
    Protocol  : TLSv1.2
    Cipher    : ECDHE-RSA-AES128-GCM-SHA256
    Session-ID: EC0E1D8CA1227AE9386A2104174ADA6C7CE7AB1D62A068DC50B5FE1F5B92CBEE
    Session-ID-ctx: 
    Master-Key: 4A72DA545F7AF1FB22F571F299FDDA8034691266ED34E94B7FF6DD71239B20F3CC84105C27399A2B1A61FFD5680ED231
    Key-Arg   : None
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    TLS session ticket lifetime hint: 100800 (seconds)
    TLS session ticket:
    0000 - d7 15 b6 8e 84 c9 af 13-f0 5d 95 16 f3 99 1e b5   .........]......
    0010 - 0d ef 79 0a ae 64 51 27-33 1e e2 d2 5b 5d 59 71   ..y..dQ'3...[]Yq
    0020 - ba cb 6d 91 1e 91 fd e2-12 2e ab 54 51 87 28 7b   ..m........TQ.({
    0030 - 92 19 de ac 62 d3 99 8a-86 2b b6 a5 85 89 b2 ce   ....b....+......
    0040 - 10 48 9b 5d 28 d8 f1 61-4e a9 b3 0c 0d ce 03 03   .H.](..aN.......
    0050 - 21 d0 fa 09 af e4 7b a7-e5 6b c2 16 c3 3a 03 ec   !.....{..k...:..
    0060 - ef 8d 8e cf de 41 ba 8c-f9 57 00 a4 24 d0 34 50   .....A...W..$.4P
    0070 - 00 c2 39 43 ec 3a f4 87-d3 d3 32 3c e6 8e 4e a9   ..9C.:....2<..N.
    0080 - ef 7e 8a 6e a1 22 1d 8a-06 97 4f 1d cc 26 9b 85   .~.n."....O..&..
    0090 - bc 3f 2a a2 cf 36 ed 6d-10 b6 39 41 98 79 34 d8   .?*..6.m..9A.y4.
    00a0 - cc 73 31 0e                                       .s1.
    Start Time: 1419973684
    Timeout   : 300 (sec)
    Verify return code: 20 (unable to get local issuer certificate)
---
250 SMTPUTF8
HELO <andy@sol.thepluginpeople.com>
250 mx.google.com at your service
mail from: meh@gmail.com
530-5.5.1 Authentication Required. Learn more at
530 5.5.1 http://support.google.com/mail/bin/answer.py?answer=14257 ej10sm48089217wib.1 - gsmtp

Authenticating for SMTP

Once a session has been setup as above, authentication can occur with: auth login.  What happens next is a 334 code response is sent by the server, what's wanted now is a base64 encoded value of the username (AAAAAAAAAAAAAA==), JEMHC has a Base64 Encoder in the Tools section.  After hitting enter, a further 334 code response is sent, next it wants the password, also base64 encoded.  If that worked, you're now authenticated.  If not, check Common Problems.

No Format
auth login
334 VXNlcm5hbWU6
AAAAAAAAAAAAAAAAAA==
334 UGFzc3dvcmQ6
BBBBBBBBBBBBBBBBBB==

 

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