Want to protect your cyber security and still get fast solutions? Ask a secure question today.Go Premium

x
?
Solved

Enable StartTLS Exchange 2010

Posted on 2014-10-13
6
Medium Priority
?
692 Views
Last Modified: 2015-11-30
I'm trying to get StartTLS enabled on my Exchange 2010 on Windows 2008R2
I have followed the steps in this link:
http://terenceluk.blogspot.com/2013/09/enabling-tls-for-exchange-server-2010.html
Locally, when I telnet to 25 and type "ehlo", I see STARTTLS listed.
Externally, when I do the same, STARTTLS is not listed.

I don't see any Event Viewer entries to show any errors.

I've read it possibly a firewall issue.  My Cisco engineer looked at the ASA and didn't see anything.  Even followed this link
http://www.cisco.com/c/en/us/support/docs/security/asa-5500-x-series-next-generation-firewalls/113336-asa83-mailserver-inside.html which I found from here:
http://www.expta.com/2014/03/troubleshooting-tls-smtp-connections-to.html

There is only one SSL Certificate which all services are using.  It was purchased from SSLS.com

What step am I missing?
0
Comment
Question by:NYTECJ
  • 4
6 Comments
 
LVL 8

Expert Comment

by:tshearon
ID: 40377526
Do you have the ESMTP Inspection feature enabled on your ASA? If so you want to disable that and see if it works.
0
 

Author Comment

by:NYTECJ
ID: 40377542
Yes, ESMTP is disabled.  As per the link I mentioned above to Cisco.
0
 
LVL 63

Accepted Solution

by:
Simon Butler (Sembee) earned 1500 total points
ID: 40377611
If it works internally, then it should work externally as well.
The only reason I can think of that it would be different is on the Receive Connector configuration, that you have an additional connector configured for internal traffic only. If you have the two default connectors (Default and Client) and their configuration is default, then there is nothing else to do with Exchange. I would be pointing the finger at the Cisco.

Simon.
0
What does it mean to be "Always On"?

Is your cloud always on? With an Always On cloud you won't have to worry about downtime for maintenance or software application code updates, ensuring that your bottom line isn't affected.

 

Author Comment

by:NYTECJ
ID: 40406857
I'm sorry for not updating this as I should.  I'm having my Cisco engineer look at it.
0
 

Author Comment

by:NYTECJ
ID: 41341506
This was resolved.  Cisco equipment was upgraded to the latest firmware.  We now have it working.
0
 

Author Closing Comment

by:NYTECJ
ID: 41341525
It was the Cisco equipment.  Upgraded the Cisco to latest firmware.
0

Featured Post

Cyber Threats to Small Businesses (Part 1)

This past May, Webroot surveyed more than 600 IT decision-makers at medium-sized companies to see how these small businesses perceived new threats facing their organizations.  Read what Webroot CISO, Gary Hayslip, has to say about the survey in part 1 of this 2-part blog series.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

This article describes Top 9 Exchange troubleshooting utilities that every Exchange Administrator should know. Most of the utilities are available free of cost. List of tools that I am going to explain in this article are:   Microsoft Remote Con…
You finally migrated Public Folders to Office 365, decommissioned the Public Folder mailbox database and since then, when you send an email from on-premise to mail-enabled Public Folders, you get the following error: "Misconfigured public folder mai…
With Secure Portal Encryption, the recipient is sent a link to their email address directing them to the email laundry delivery page. From there, the recipient will be required to enter a user name and password to enter the page. Once the recipient …
Exchange organizations may use the Journaling Agent of the Transport Service to archive messages going through Exchange. However, if the Transport Service is integrated with some email content management application (such as an antispam), the admini…
Suggested Courses

580 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question