Sample SMTP Session with Auth Login

by Oliver 13. June 2013 15:27

This post is most of all a log drop of an SMTP session I had with our mail server over telnet. We use hMailServer for all of our own and hosted e-mail accounts. Today, I set up a new account to use for our SQL servers to report any problems. I couldn't get SQL Server's DatabaseMail to successfully send any e-mail so I went to find out what might be wrong by myself. Here's my first successful chat with our mail server using AUTH LOGIN, i.e. username and password authentication: 1: 220 mail.teamaton.com ESMTP                                   // started session with: telnet mail.teamaton.com 25 2: hello                                                         // my first try - not quite ;-) 3: 502 Use HELO/EHLO first. 4: HELO                                                          // ok, I got you 5: 501 HELO Invalid domain address. 6: HELO                                                          // say again? 7: 502 Use HELO/EHLO first. 8: EHLO 25.0.153.55                                              // send a host name of the computer you're on 9: 250-mail.teamaton.com 10: 250-SIZE 15000000 11: 250 AUTH LOGIN 12: MAIL FROM: <sql*******@teamaton.com>                          // the from address to use for the e-mail 13: 250 OK 14: RCPT TO: <oliver*******@******.com> // trying to set a recipient's address 15: 530 SMTP authentication is required. 16: AUTH LOGIN                                                    // initiating login 17: 334 VXNlcm5hbWU6                                              // the server is asking for my username in base64 encoding 18: c3FsLXNl***************vbi5jb20=                              // sending my username in base64 encoding 19: 334 UGFzc3dvcmQ6                                              // the server is asking for my password in base64 encoding 20: YkZwN***************A1dng=                                    // sending my password in base64 encoding 21: 535 Authentication failed. Restarting authentication process. // oops, I copied some invisible character from that encoding web page 22: auth login                                                    // try again 23: 502 Unimplemented command.                                    // case seems to matter 24: AUTH LOGIN 25: 334 VXNlcm5hbWU6 26: c3FsLXNl***************vbi5jb20= 27: 334 UGFzc3dvcmQ6 28: YkZwN***************A1dng= 29: 235 authenticated.                                            // finally! 30: DATA                                                          // set the body of the e-mail 31: 503 Must have sender and recipient first.                     // hm, I thought I set the sender already… 32: MAIL FROM: <sql*******@teamaton.com>                          // oh well, set it again 33: 503 Issue a reset if you want to start over                   // I didn't want to start over! 34: RCPT TO: <oliver*******@******.com>                           // set only the missing recipient, then 35: 250 OK 36: DATA                                                          // now, set the mail body 37: 354 OK, send. 38: Test mail here. 39:  40: .                                                             // mark the end of the mail body 41: 250 Queued (11.247 seconds) 42: 421 Connection timeout.                                       // that's what happened after a while when I left the shell open 43:  44: Connection to host lost. 45:  46: C:\Users\Oliver> Every line that starts with a status code was sent by the server, the rest of them is what I entered. Just for the record.

About Oliver

shades-of-orange.com code blog logo I build web applications using ASP.NET and have a passion for javascript. Enjoy MVC and Orchard CMS, and I do TDD whenever I can. I like clean code. Love to spend time with my wife and our three children. My profile on Stack Exchange, a network of free, community-driven Q&A sites

About Anton

shades-of-orange.com code blog logo I'm a software developer at teamaton. I code in C# and work with MVC, Orchard, SpecFlow, Coypu and NHibernate. I enjoy beach volleyball, board games and Coke.