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Articles I've written for customers on IT issues.
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IT_Articles/2020/Manual_Email_Server_Interac.../docs/6.tex

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  1. \documentclass[11pt]{article}
  2. %Gummi|065|=)

  3. \title{\textbf{}}
  4. \usepackage{graphicx}
  5. \usepackage{caption  }
  6. \author{Steak Electronics}
  7. %\date{06/4/19}

  8. \begin{document}
  9. 

  10. %\maketitle

  11. \textbf{Email Stuff}
  12. 

  13. \vspace{0.2in}
  14. 

  15. %\textbf{Todo}

  16. \section{Manual Email Server Interaction}
  17. How to send emails manually. This is essential for troubleshooting automated email systems.
  18. 

  19. \section{Basics}
  20. 

  21. \begin{verbatim}
  22. openssl s_client -debug -starttls smtp -crlf -connect smtp.emailprovider.com:465
  23. then continue with 
  24. EHLO hostname
  25. 

  26. AUTH 
  27. etc...
  28. \end{verbatim}
  29. 

  30. 

  31. Here's an example:
  32. 

  33. \begin{verbatim}
  34. Compression: NONE
  35. Expansion: NONE
  36. No ALPN negotiated
  37. SSL-Session:
  38.     Protocol  : TLSv1.2
  39.     Cipher    : ECDHE-RSA-AES128-GCM-SHA256
  40.     Session-ID: 480E968D62206D936801683C3BB12679DCB5CEDB0B20F4C3C2EB9DC97A54FAF4
  41.     Session-ID-ctx:
  42.     Master-Key: BAB3C9AD7E209D2A979A621731BCB6A0B4368EEE03E2B99CF884D2671E2D62A1A365EEB50FC881CA2E4FD666082027BA
  43.     Key-Arg   : None
  44.     PSK identity: None
  45.     PSK identity hint: None
  46.     SRP username: None
  47.     TLS session ticket lifetime hint: 300 (seconds)
  48.     TLS session ticket:
  49.     0000 - 26 e3 0c d9 a7 0e b1 88-52 ce 35 aa a0 8d bd 40   &.......R.5....@
  50.     0010 - 0c 39 e4 60 04 59 06 bb-b2 7e 35 f9 56 36 d1 46   .9.`.Y...~5.V6.F
  51.     0020 - d2 8c 48 29 44 fa 9f 2b-cd af fc 9a 68 b0 b8 63   ..H)D..+....h..c
  52.     0030 - 35 06 cd ba 67 57 bf c4-84 19 5a 05 fd a7 62 51   5...gW....Z...bQ
  53.     0040 - 1c 63 d7 b0 b4 ce 62 9f-66 13 7b 4c 74 54 86 fa   .c....b.f.{LtT..
  54.     0050 - 3b 31 e1 e1 bd 19 29 e8-76 c2 6c 45 db 1d 32 50   ;1....).v.lE..2P
  55.     0060 - 60 63 ec 38 a3 e5 de 26-d6 27 c6 26 60 09 1a 59   `c.8...&.'.&`..Y
  56.     0070 - 59 e9 97 b4 07 9f 6c fc-46 cb 9e 0b 40 57 8f 71   Y.....l.F...@W.q
  57.     0080 - 20 98 54 06 38 42 47 c1-e6 fd 74 92 dc 11 a5 97    .T.8BG...t.....
  58.     0090 - 5d 81 7e 0b 66 b7 8e aa-c0 61 48 0c 90 84 ac 2d   ].~.f....aH....-
  59. 

  60.     Start Time: 1590893833
  61.     Timeout   : 300 (sec)
  62.     Verify return code: 0 (ok)
  63. ---
  64. 250 PIPELINING
  65. EHLO localhost
  66. write to 0x1c0dd20 [0x1c17853] (45 bytes => 45 (0x2D))
  67. 0000 - 17 03 03 00 28 2a 65 16-62 f5 2c 8c e5 d9 f2 ef   ....(*e.b.,.....
  68. 0010 - bb 8a ac 3a 6a dc db 32-79 56 7f 86 90 2e ed 44   ...:j..2yV.....D
  69. 0020 - 6e 6a ea 12 64 bb f8 1e-95 7e 63 16 c5            nj..d....~c..
  70. read from 0x1c0dd20 [0x1c13303] (5 bytes => 5 (0x5))
  71. 0000 - 17 03 03 00 a7                                    .....
  72. read from 0x1c0dd20 [0x1c13308] (167 bytes => 167 (0xA7))
  73. 0000 - 80 ae b0 b8 00 a2 d6 6b-47 42 2c 5d 30 1c 04 bd   .......kGB,]0...
  74. 0010 - 5c bb 84 61 20 5a 2e 0d-c5 79 28 a9 21 d6 ad 1b   \..a Z...y(.!...
  75. 0020 - 99 e5 fc da a1 fb da bc-70 9e 9b ac 5a e1 0f 8e   ........p...Z...
  76. 0030 - bb c8 6d cb 2e 27 af 9b-4a 6a e8 17 69 31 63 14   ..m..'..Jj..i1c.
  77. 0040 - 24 68 d7 6b cc a7 dc 24-7c d6 4b fa 2a 3e 38 61   $h.k...$|.K.*>8a
  78. 0050 - 58 57 4d e8 1c e7 66 3c-22 0f 07 62 42 14 e7 78   XWM...f<"..bB..x
  79. 0060 - 86 8a 6c 6f 8f 79 06 f6-dc 33 b5 e9 ec db b8 b4   ..lo.y...3......
  80. 0070 - 0e 7d d7 08 17 cd 4d b3-ac 16 79 08 87 df 31 95   .}....M...y...1.
  81. 0080 - 03 8d 9e 8c 25 09 ca 38-d0 be ee 45 38 d8 c4 a5   ....%..8...E8...

  82. 0090 - c3 90 44 23 5d e7 9b 1b-c0 40 d2 cc 40 c5 4a e4   ..D#]....@..@.J.
  83. 00a0 - 25 38 8b 05 2f b2 33                              %8../.3

  84. 250-www192.vfemail.net
  85. 250-8BITMIME
  86. 250-AUTH PLAIN
  87. 250-BURL imap
  88. 250-CHUNKING
  89. 250-ENHANCEDSTATUSCODES
  90. 250-SIZE 78643200
  91. 250 PIPELINING
  92. \end{verbatim}
  93. Here you might enter at the prompt
  94. \\
  95. \\
  96. AUTH LOGIN
  97. 

  98. But that will fail:
  99. 

  100. \begin{verbatim}
  101. AUTH LOGIN
  102. write to 0x1c0dd20 [0x1c17853] (41 bytes => 41 (0x29))
  103. 0000 - 17 03 03 00 24 2a 65 16-62 f5 2c 8c e6 59 01 74   ....$*e.b.,..Y.t

  104. 0010 - 10 99 f5 d2 e6 75 88 d3-b9 58 0e 92 78 fc f1 ad   .....u...X..x...
  105. 0020 - c6 aa 50 2a 6c f4 cf e5-dd                        ..P*l....
  106. read from 0x1c0dd20 [0x1c13303] (5 bytes => 5 (0x5))
  107. 0000 - 17 03 03 00 3a                                    ....:
  108. read from 0x1c0dd20 [0x1c13308] (58 bytes => 58 (0x3A))
  109. 0000 - 80 ae b0 b8 00 a2 d6 6c-bf e5 f8 3d 5a 39 93 2b   .......l...=Z9.+
  110. 0010 - f8 a2 12 03 0f 0f 5c a3-95 0a 6c b6 d9 fa 3d 09   ......\...l...=.
  111. 0020 - 73 f7 5c 26 8c 41 aa cf-87 0f 65 61 52 7d ec f7   s.\&.A....eaR}..
  112. 0030 - 4a fe cd a4 f8 3e be 48-a3 92                     J....>.H..
  113. 504 5.5.4 Authentication failed.
  114. 

  115. \end{verbatim}
  116. 

  117. 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).
  118. 

  119. Unfortunately, ssmtp (which I'm using) doesn't support plain. from ssmtp manual:
  120. 

  121. Specifies mechanism for SMTP authentication. (Only LOGIN and CRAM-MD5)
  122. 

  123. If you instead type AUTH PLAIN or auth plain, it will respond with 334. It is then waiting for credentials.
  124. \begin{verbatim}
  125. 

  126. ref: https://wiki.zoneminder.com/SMS_Notifications
  127. \end{verbatim}
  128. 

  129. You can also compare logs in /var/log/mail.log
  130. Here's a working example:
  131. 

  132. \begin{verbatim}
  133. Jun 16 01:01:02 server sSMTP[19958]: Creating SSL connection to host
  134. Jun 16 01:01:02 server sSMTP[19958]: SSL connection using DHE_RSA_AES_256_CBC_SHA1
  135. Jun 16 01:01:04 server sSMTP[19958]: Sent mail for .com (221 2.0.0 Bye) uid=0 username=root outbytes=91617
  136. Jun 16 01:01:04 server sSMTP[19978]: Creating SSL connection to host
  137. Jun 16 01:01:05 server sSMTP[19978]: SSL connection using DHE_RSA_AES_256_CBC_SHA1
  138. Jun 16 01:01:06 server sSMTP[19978]: Sent mail for .com (221 2.0.0 Bye) uid=0 username=root outbytes=93751
  139. Jun 18 13:30:31 server sSMTP[18220]: Creating SSL connection to host
  140. Jun 18 13:30:32 server sSMTP[18220]: 220 smtp.mxes.net ESMTP Postfix 03
  141. Jun 18 13:30:32 server sSMTP[18220]: EHLO s.com
  142. Jun 18 13:30:32 server sSMTP[18220]: 250 CHUNKING
  143. Jun 18 13:30:32 server sSMTP[18220]: STARTTLS
  144. Jun 18 13:30:32 server sSMTP[18220]: 220 2.0.0 Ready to start TLS
  145. Jun 18 13:30:32 server sSMTP[18220]: SSL connection using DHE_RSA_AES_256_CBC_SHA1
  146. Jun 18 13:30:32 server sSMTP[18220]: EHLO s.com
  147. Jun 18 13:30:32 server sSMTP[18220]: 250 CHUNKING
  148. Jun 18 13:30:32 server sSMTP[18220]: AUTH LOGIN
  149. Jun 18 13:30:32 server sSMTP[18220]: 334 lslslsls
  150. Jun 18 13:30:32 server sSMTP[18220]: somethuing
  151. Jun 18 13:30:32 server sSMTP[18220]: 334 something else6
  152. Jun 18 13:30:32 server sSMTP[18220]: somehashedstuff
  153. Jun 18 13:30:32 server sSMTP[18220]: 235 2.7.0 Authentication successful
  154. Jun 18 13:30:32 server sSMTP[18220]: MAIL FROM:<person@some.com>
  155. Jun 18 13:30:32 server sSMTP[18220]: 250 2.1.0 Ok
  156. Jun 18 13:30:32 server sSMTP[18220]: RCPT TO:<fgdfg>
  157. Jun 18 13:30:33 server sSMTP[18220]: 250 2.1.5 Ok
  158. Jun 18 13:30:33 server sSMTP[18220]: DATA
  159. Jun 18 13:30:33 server sSMTP[18220]: 354 End data with <CR><LF>.<CR><LF>
  160. Jun 18 13:30:33 server sSMTP[18220]: Received: by .com (sSMTP sendmail emulation); Thu, 18 Jun 2020 13:30:30 -0400
  161. Jun 18 13:30:33 server sSMTP[18220]: From: "C" <c@com>
  162. Jun 18 13:30:33 server sSMTP[18220]: Date: Thu, 18 Jun 2020 13:30:30 -0400
  163. Jun 18 13:30:33 server sSMTP[18220]: To: j
  164. Jun 18 13:30:33 server sSMTP[18220]: Subject: My email check
  165. Jun 18 13:30:33 server sSMTP[18220]:
  166. Jun 18 13:30:33 server sSMTP[18220]: Hello, World
  167. Jun 18 13:30:34 server sSMTP[18220]: .
  168. Jun 18 13:30:34 server sSMTP[18220]: 250 2.0.0 Ok: queued as 3B1D6759AF
  169. Jun 18 13:30:34 server sSMTP[18220]: QUIT
  170. Jun 18 13:30:34 server sSMTP[18220]: 221 2.0.0 Bye
  171. Jun 18 13:30:34 server sSMTP[18220]: Sent mail for c (221 2.0.0 Bye) uid=1000 username=c outbytes=439
  172. 

  173. \end{verbatim}
  174. 

  175. Here is another non working one.
  176. \begin{verbatim}
  177. Jun 18 17:35:46 zmctankhome sSMTP[22488]: Set MailHub="smtp.mxes.net"
  178. Jun 18 17:35:46 zmctankhome sSMTP[22488]: via SMTP Port Number="587"
  179. Jun 18 17:35:47 zmctankhome sSMTP[22488]: Creating SSL connection to host
  180. Jun 18 17:35:47 zmctankhome sSMTP[22488]: 220 smtp.mxes.net ESMTP Postfix 03
  181. Jun 18 17:35:47 zmctankhome sSMTP[22488]: EHLO .com
  182. Jun 18 17:35:47 zmctankhome sSMTP[22488]: 250 CHUNKING
  183. Jun 18 17:35:47 zmctankhome sSMTP[22488]: STARTTLS
  184. Jun 18 17:35:47 zmctankhome sSMTP[22488]: 220 2.0.0 Ready to start TLS
  185. Jun 18 17:35:48 zmctankhome sSMTP[22488]: SSL connection using ECDHE_RSA_AES_256_GCM_SHA384
  186. Jun 18 17:35:48 zmctankhome sSMTP[22488]: EHLO .com
  187. Jun 18 17:35:48 zmctankhome sSMTP[22488]:
  188. Jun 18 17:35:48 zmctankhome sSMTP[22488]:  (.com)
  189. 

  190. \end{verbatim}
  191. Notice the TLS / SSL encryption is different. That can be a deal breaker. Ouch. Otherwise both are Debian (one is 9, the other 10).
  192. 

  193. 

  194. \end{document}