Solved

Enable StartTLS Exchange 2010

Posted on 2014-10-13
6
289 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
[X]
Welcome to Experts Exchange

Add your voice to the tech community where 5M+ people just like you are talking about what matters.

  • Help others & share knowledge
  • Earn cash & points
  • Learn & ask questions
  • 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 500 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
Office 365 Training for Admins - 7 Day Trial

Learn how to provision tenants, synchronize on-premise Active Directory, implement Single Sign-On, customize Office deployment, and protect your organization with eDiscovery and DLP policies.  Only from Platform Scholar.

 

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

On Demand Webinar: Networking for the Cloud Era

Did you know SD-WANs can improve network connectivity? Check out this webinar to learn how an SD-WAN simplified, one-click tool can help you migrate and manage data in the cloud.

Question has a verified solution.

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

How to resolve IMCEAEX NDRs in Exchange or Exchange Online related to invalid X500 addresses.
After hours on line I found a solution which pointed to the inherited Active Directory permissions . You have to give/allow permissions to the "Exchange trusted subsystem" for the user in the Active Directory...
This video demonstrates how to sync Microsoft Exchange Public Folders with smartphones using CodeTwo Exchange Sync and Exchange ActiveSync. To learn more about CodeTwo Exchange Sync and download the free trial, go to: http://www.codetwo.com/excha…
The Email Laundry PDF encryption service allows companies to send confidential encrypted  emails to anybody. The PDF document can also contain attachments that are embedded in the encrypted PDF. The password is randomly generated by The Email Laundr…

622 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