Test Virtual Email Security with Two Exchange 2010 Internally

[mohamed.fawzy2012]

 i installed Active directory 2088R2 with exchange server 2010  

1) first exchange server (mail.x.com)   vlan 40"192.168.40.245"      i want to use it as internally

2) second exchange server (mail.y.com) vlan 42"192.168.42.245    i want to use it as externally

3) installed virtual ESA in vlan 40 "192.168.40.51" and upgraded to version 11 

4) i tested to send mail from each mail server to itself , it is working fine

5) i tested to send mail server to the other mail server ( from x to y) but failed

two vlan in the same network 

i don't know what is the root cause and what i am missing in configuration of ESA 

[Libin Varghese]

Hi, 

What is the error seen in the message tracking or mail logs for emails sent from X to Y through the ESA?

You can attempt to telnet from the ESA to each server over port 25 to confirm the traffic is allowed.

It could be an issue with the network routes configured on the ESA. 

Regards 

Libin Varghese 

[mohamed.fawzy2012]

1) i tried to telnet fro ESA and that is the result , i don't know that is right or wrong

vesa.connectps.local> telnet 192.168.40.245 25

Trying 192.168.40.245...
Connected to 192.168.40.245.
Escape character is '^]'.
220 WIN-JL1SE184DIF.connectps.local Microsoft ESMTP MAIL Service ready at Sat, 2 Dec 2017 12:49:22 -0800

vesa.connectps.local> telnet 192.168.42.245 25

Trying 192.168.42.245...
Connected to 192.168.42.245.
Escape character is '^]'.
220 ExternalAD.external.local Microsoft ESMTP MAIL Service ready at Sun, 3 Dec 2017 12:51:28 +0200

2) there is no result output from message tracking 

[Jernej Vodopivec]

Have you configured Send and Receive connectors on both Exchange's correctly? Have you configured RAT, SMTP routes etc. on ESA correctly? Try to manually send email: a) from Exchange X to ESA: https://technet.microsoft.com/en-us/library/bb123686(v=exchg.160).aspx (step 3) - if ESA refuses the email copy-paste the text output b) from ESA to Exchange Y: run same procedure.. if Exchange Y refuses the email, copy paste the output

[Libin Varghese]

The telnet result would suggest the ESA has no issues sending emails to these two servers.

You would need to trace the email seeing the issue to see if even reaches the ESA.

A send connector from the server would need to point to the ESA and the ESA would try to deliver the same email based on the SMTP routes of DNS records for the destination domain.

Regards,

Libin Varghese