IT_Articles/2020/Manual_Email_Server_Interaction/docs/3.tex~

\documentclass[11pt]{article}
%Gummi|065|=)
\title{\textbf{}}
\usepackage{graphicx}
\usepackage{caption  }
\author{Steak Electronics}
\date{06/4/19}
\begin{document}

%\maketitle
\textbf{Nextcloud Research}

\vspace{0.2in}

%\textbf{Todo}
\section{Manual Email Server Interaction}
How to send emails manually. This is essential for troubleshooting automated email systems.

\section{Basics}

\begin{verbatim}
openssl s_client -debug -starttls smtp -crlf -connect smtp.emailprovider.com:465
then continue with 
EHLO hostname
AUTH 
etc...
\end{verbatim}


Here's an example:

\begin{verbatim}
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
    Protocol  : TLSv1.2
    Cipher    : ECDHE-RSA-AES128-GCM-SHA256
    Session-ID: 480E968D62206D936801683C3BB12679DCB5CEDB0B20F4C3C2EB9DC97A54FAF4
    Session-ID-ctx:
    Master-Key: BAB3C9AD7E209D2A979A621731BCB6A0B4368EEE03E2B99CF884D2671E2D62A1A365EEB50FC881CA2E4FD666082027BA
    Key-Arg   : None
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    TLS session ticket lifetime hint: 300 (seconds)
    TLS session ticket:
    0000 - 26 e3 0c d9 a7 0e b1 88-52 ce 35 aa a0 8d bd 40   &.......R.5....@
    0010 - 0c 39 e4 60 04 59 06 bb-b2 7e 35 f9 56 36 d1 46   .9.`.Y...~5.V6.F
    0020 - d2 8c 48 29 44 fa 9f 2b-cd af fc 9a 68 b0 b8 63   ..H)D..+....h..c
    0030 - 35 06 cd ba 67 57 bf c4-84 19 5a 05 fd a7 62 51   5...gW....Z...bQ
    0040 - 1c 63 d7 b0 b4 ce 62 9f-66 13 7b 4c 74 54 86 fa   .c....b.f.{LtT..
    0050 - 3b 31 e1 e1 bd 19 29 e8-76 c2 6c 45 db 1d 32 50   ;1....).v.lE..2P
    0060 - 60 63 ec 38 a3 e5 de 26-d6 27 c6 26 60 09 1a 59   `c.8...&.'.&`..Y
    0070 - 59 e9 97 b4 07 9f 6c fc-46 cb 9e 0b 40 57 8f 71   Y.....l.F...@W.q
    0080 - 20 98 54 06 38 42 47 c1-e6 fd 74 92 dc 11 a5 97    .T.8BG...t.....
    0090 - 5d 81 7e 0b 66 b7 8e aa-c0 61 48 0c 90 84 ac 2d   ].~.f....aH....-

    Start Time: 1590893833
    Timeout   : 300 (sec)
    Verify return code: 0 (ok)
---
250 PIPELINING
EHLO localhost
write to 0x1c0dd20 [0x1c17853] (45 bytes => 45 (0x2D))
0000 - 17 03 03 00 28 2a 65 16-62 f5 2c 8c e5 d9 f2 ef   ....(*e.b.,.....
0010 - bb 8a ac 3a 6a dc db 32-79 56 7f 86 90 2e ed 44   ...:j..2yV.....D
0020 - 6e 6a ea 12 64 bb f8 1e-95 7e 63 16 c5            nj..d....~c..
read from 0x1c0dd20 [0x1c13303] (5 bytes => 5 (0x5))
0000 - 17 03 03 00 a7                                    .....
read from 0x1c0dd20 [0x1c13308] (167 bytes => 167 (0xA7))
0000 - 80 ae b0 b8 00 a2 d6 6b-47 42 2c 5d 30 1c 04 bd   .......kGB,]0...
0010 - 5c bb 84 61 20 5a 2e 0d-c5 79 28 a9 21 d6 ad 1b   \..a Z...y(.!...
0020 - 99 e5 fc da a1 fb da bc-70 9e 9b ac 5a e1 0f 8e   ........p...Z...
0030 - bb c8 6d cb 2e 27 af 9b-4a 6a e8 17 69 31 63 14   ..m..'..Jj..i1c.
0040 - 24 68 d7 6b cc a7 dc 24-7c d6 4b fa 2a 3e 38 61   $h.k...$|.K.*>8a
0050 - 58 57 4d e8 1c e7 66 3c-22 0f 07 62 42 14 e7 78   XWM...f<"..bB..x
0060 - 86 8a 6c 6f 8f 79 06 f6-dc 33 b5 e9 ec db b8 b4   ..lo.y...3......
0070 - 0e 7d d7 08 17 cd 4d b3-ac 16 79 08 87 df 31 95   .}....M...y...1.
0080 - 03 8d 9e 8c 25 09 ca 38-d0 be ee 45 38 d8 c4 a5   ....%..8...E8...
0090 - c3 90 44 23 5d e7 9b 1b-c0 40 d2 cc 40 c5 4a e4   ..D#]....@..@.J.
00a0 - 25 38 8b 05 2f b2 33                              %8../.3
250-www192.vfemail.net
250-8BITMIME
250-AUTH PLAIN
250-BURL imap
250-CHUNKING
250-ENHANCEDSTATUSCODES
250-SIZE 78643200
250 PIPELINING
\end{verbatim}
Here you might enter at the prompt
\\
\\
AUTH LOGIN

But that will fail:

\begin{verbatim}
AUTH LOGIN
write to 0x1c0dd20 [0x1c17853] (41 bytes => 41 (0x29))
0000 - 17 03 03 00 24 2a 65 16-62 f5 2c 8c e6 59 01 74   ....$*e.b.,..Y.t
0010 - 10 99 f5 d2 e6 75 88 d3-b9 58 0e 92 78 fc f1 ad   .....u...X..x...
0020 - c6 aa 50 2a 6c f4 cf e5-dd                        ..P*l....
read from 0x1c0dd20 [0x1c13303] (5 bytes => 5 (0x5))
0000 - 17 03 03 00 3a                                    ....:
read from 0x1c0dd20 [0x1c13308] (58 bytes => 58 (0x3A))
0000 - 80 ae b0 b8 00 a2 d6 6c-bf e5 f8 3d 5a 39 93 2b   .......l...=Z9.+
0010 - f8 a2 12 03 0f 0f 5c a3-95 0a 6c b6 d9 fa 3d 09   ......\...l...=.
0020 - 73 f7 5c 26 8c 41 aa cf-87 0f 65 61 52 7d ec f7   s.\&.A....eaR}..
0030 - 4a fe cd a4 f8 3e be 48-a3 92                     J....>.H..
504 5.5.4 Authentication failed.

\end{verbatim}

If you look at the EHLO, it responds with what auth it supports. In this case, AUTH PLAIN. So it accepts plain text passwords (over an encrypted session of course).

Unfortunately, ssmtp doesn't support plain. from ssmtp manual:

Specifies mechanism for SMTP authentication. (Only LOGIN and CRAM-MD5)


\end{document}