Exchange 2007 configuration for sending emails from SupportSuite

[D0ubleStakked]

All,
I have been working with Kayako Support for the past few days to troubleshoot my issue, and now that it is solved, I wanted to share my configuration with everyone to hopefully work through issues that anyone else is having.

I am running an owned instance of SupportSuite 3.20.02, and for several days now I have been unable to send emails from SupportSuite to either internal or external email addresses.

Here is my solution:

Our mailserver is Exchange 2007 Standard SP1, and in the Exchange Management Console, make the following configuration changes:

Server Configuration > Hub Transport > Receive Connectors

create a new Receive Connector with the following configuration:
General > Name = SupportSuite
General > Protocol Logging Level = None
General > FQDN = <internal mailserver hostname>
General > Max message size = 10240
Network > local IP addresses = (All Available IPv4 addresses) port 25
Network > Receive email from IP addresses = <IP of my supportsuite server>
Authentication > check Basic Authentication
Authentication > check Integrated Windows Authentication
Permissions Groups > check Exchange Users

then in the SupportSuite Admin CP, make the following configuration changes:

under Settings > CPU Optimization & Server > SMTP settings, enter in your SMTP Auth credentials, and set "Use SMTP Authentication" to YES.

lastly, test connectivity from the server running SupportSuite to your Exchange server by using telnet (instructions below assume Windows O/S).

1.) start > run > cmd
2.) telnet <mail_server> 25
3.) ehlo <mail_server>
4.) AUTH LOGIN
5.) <base64_encoded_username>
6.) <base64_encoded_password>

At this point, I received the "235 2.7.0 Authentcation successful" message, and I was able to complete my email send through telnet.

After the "ehlo <mail_server>" command, I see the following returned to me:
250-<mail_server_hostname> Hello [<support_suite_IP_address>]
250-SIZE
250-PIPLINING
250-DSN
250-ENHANCEDSTATUSCODES
250-AUTH NTLM LOGIN
250-8BITMIME
250-BINARYMIME
250 CHUNKING

I found that the "250-AUTH NTLM LOGIN" was necessary in order to have the "ehlo <mail_server>" and "AUTH LOGIN" statements work correctly.

Now I am able to send emails from SupportSuite to our Exchange 2007 SP1 server using SMTP authentication.

I hope this helps anyone else who might be fighting the same issues I was.

Regards,
-Brian

[Jamie Edwards]

Thanks for taking the time to do the write-up, Brian