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

[ceebster]

Hi Guys

Have big issues trying to get our exchange 2007 server to pass mail to the big wide world.

Internally is fine, and i have followed the instrcutions to have a user, but when send mail when i put one in

Any other ideas?


Thanks


Chris

[D0ubleStakked]

Chris,
I'm assuming you're using an owned (self-hosted) SupporSuite, and not Kayako's hosted offering...
Have you tried using telnet from a command-line to test sending email to an external address from your SupportSuite server?
I experienced this exact issue with other tools, not SupportSuite, when we first installed Exchange 2007 and we found it was error in how we had our receive connector setup under (Server Configuration > Hub Transport > Receive connector)

Do you have other tools in your network successfully relaying emails through Exchange 2007 to external addresses?

-Brian

[ceebster]

Hi Brian

Thanks for the reply

I have it hosted on my own server here in school.

I was struggling with the telnet commands, but i was able to create a nother connector in Exch2007.

The only thing was when i used my authenticated user from AD, into SupportSuite, it would not even send any internal mail from hte helpdesk.

Is there any guidlines how to send mail from telnet?

if you feel we are off topic from the forum, my email is cbutler@arthurterry.bham.sch.uk or msn ceebster@gmail.com


Thanks again


Chris

[D0ubleStakked]

Chris,
For using telnet to send mail, try the following on the SupportSuite server:

(I'm assuming Windows here and not Linux) :
1.) start > run > cmd
2.) telnet your_mail_server_name 25 enter
3.) type "ehlo your_mail_server_name"and press enter
- you should get back a list of messages that all start with "250-"

4.) type "AUTH LOGIN" and press enter
- you should be prompted for a username:

5.) type "<base64_encoded_username>" and press enter
- you should be prompted for a password:

6.) type "<base64_encoded_password>"and press enter

7.) type "mail from: <sender's email address> "and press enter
- you should receive a "250 2.1.0 Sender OK" message

8.) type "rcpt to: <recipient's email address> "and press enter
- you should receive a "250 2.1.5 Recipient OK" message
- if you receive a "550 5.7.1 Unable to relay" message, then something isn't configured correctly on your Exchange server.

9.) type "data"and press enter

10.) <type in your message here>

11.) type enter "." enter
- you should receive confirmation that your message has been queued for delivery.


2 things to note:
1.) for step's 5 & 6, you'll need the base64 encoded values, not the plain-text values. You can use a website like these guys (Base64 Online - base64 decode and encode) to get the base64 values.

2.) telnet is fairly unforgiving, and doesn't like the backspace or delete keys. so if you made a typo, don't try to delete the bad text and re-enter it. Just type


Hope this helps.
-Brian

[ceebster]

Hi brian

Good news so far - followed you fantastic instructions - i got my mail server to send to an external address. :-)

What do you think i should try next - settings support suite back up and trying that?

Thanks in advance


Chris

[D0ubleStakked]

Chris,
just to make sure I follow you, where did you run the telnet test from? your local desktop/laptop or the server that SupportSuite will run on?

If your telnet test worked from your SupportSuite server, then yes, go ahead and set SupportSuite back up and try it out again.

For everyone's knowledge here on the forums, did you have to change anything in Exchange to get your telnet test to work?

-Brian

[ceebster]

Hi Brian

Yes - i did the test from Support S server.

I also followed your orginal instructions about setting up the Hub converter, and i made sure the user i was using for the support suite, was a member of the exchnage membership groups.

Will update after i have rebuilt my server

Thanks


Chris

[D0ubleStakked]

Looks like you did everything right, Chris. Nice work.

In Exchange, did you add a new Hub Transport > Receive Connector for SupportSuite, or did you modify the Default connector? Just make sure the mailflow from Outlook and OWA still work, and IMAP or ActiveSync if you're using those too. Anytime I change something in Exchange, I re-test mailflow. The last thing you want is for SupportSuite to work correctly, but Outlook to not work at all.

Let us know if SupportSuite works for you after you get it re-installed.

-Brian

[ceebster]

Hi Brian

I created a seperate new connector - we have two connectors (well 3 now) a default for normal smtp port 25 mail, and then a client for outlook - we also use activesync for phones too.

Hope fully this should do the trick

Keep you in the loop


Thanks


Chris