Cannot get ActionMailer working with MS Exchange via SMTP

Check what authentication schemes are enabled

It could be: none, plain, login, cram_md5, NTLM, StartTLS

• Using Telnet to connect to Exchange 2003 POP3 mailboxes and using SMTP to send e-mail for troubleshooting purposes
  • http://www.msexchange.org/tutorials/telnet-exchange2003-pop3-smtp-troubleshooting.html
    • Scroll down to: Connecting to SMTP
    • What did EHLO return?
      • "250-AUTH LOGIN" or "250-AUTH=LOGIN" indicate that you need to authenticate.
      • "250-AUTH" (with nothing else following on that line!) seems to indicate that you should NOT authenticate yourself! Otherwise you will get the error:
        • "504 5.7.4 Unrecognized authentication type"

How to properly access Exchange

Good resources that should help you to understand and troubleshoot it.

• The EHLO verb and SMTP extensions
  • http://cr.yp.to/smtp/ehlo.html
• The AUTH Command
  • http://www.samlogic.net/articles/smtp-commands-reference-auth.htm
• How to Use Telnet to Send SMTP Email to Exchange 2007 and 2010
  • http://www.expta.com/2010/03/how-to-use-telnet-to-send-smtp-email-to.html
• Using telnet to test authenticated relay in Exchange
  • http://www.dasblinkenlichten.com/?p=190

How you could change Exchange to fix the problem

(instead of changing how you access Exchange)

• How to enable auth login on smtp server exchange 2010
  • http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_26538583.html
• How to Enable "Auth Login" authenticaton on Exchange
  • http://www.advancedintellect.com/post/2011/03/02/Exchange-2010-and-SMTP-settings.aspx
• Error in establishing SMTP connection, Error: 504 5.7.4 Unrecognized authentication type
  • (how to change the Exchange 2010 configuration to "accept mail from third part product" as mentioned by Anil K Singh)
    • http://social.technet.microsoft.com/Forums/en-US/exchange2010/thread/93ad411a-0da2-4494-a45e-8cbb793aeca9/

Redmine specific

Helpful for Ruby on Rails

• How to configure Redmine to mail to MS Exchange server
  • http://www.redmine.org/projects/redmine/wiki/HowTo_configure_Redmine_to_mail_to_MS_Exchange_server
    • "MS Exchange will not require authentication information for outgoing (SMTP) email"
    • My configuration file is still at config/email.yml (in Redmine 1.2)
• Helpful troubleshooting tips for Ruby on Rails code
  • See answer from firien
• How to use ruby-ntlm in case Exchange requires NTLM
  • Unrecognized authentication type when doing an Auth to Exchange from Rails
• How to use the TLS option
  • http://www.redmineblog.com/articles/setup-redmine-to-send-email-using-gmail/

had similar network issues. use the code below in irb to get debug info right in the console.

require 'net/smtp'smtp = Net::SMTP.new('ip_or_dns_address', port)smtp.debug_output = $stdoutsmtp.enable_starttls_auto#skip if not neededsmtp.start("domain", "user", "password", auth_type)

never really found out what the issue was. they moved the exchange server and the production server stopped sending emails. im not really an IT guy but there were different debug logs depending which part of the network i was on. finally "solved" the problem by sending unauthenticated email...

You could connect to the SMTP server and query the supported authentication methods:

telnet smtp.server.net 25EHLO

The server should respond with at least one line that starts with 250-AUTH. After that the supported authentication methods are listed. Chances are that the Exchange server only supports authentication via GSSAPI or NTLM. In the latter case you might be able to get it to work with the ruby-ntlm gem and the ntlm authentication method. (See http://www.breckenedge.com/configuration-of-ruby-on-rails-actionmailer-for-microsoft-exchange-smtp)