Solved

Exchange 2003 SMTP TLS connection

Posted on 2007-04-05
7
2,116 Views
Last Modified: 2013-11-30
Here is the scenerio.  We recently implemented a third party spam filter, our MX record points to them they clean the mail and forward it to us.  We have still been getting a ton of spam that is coming directly to our mail server.  We cant lock down port SMTP because I have mobile users who connect via pop and SMTP for their mail.  I created a second SMTP virtual server on port 2525 and have all mail from our spam company sent to through that connector and I am trying to set the original virtual server on port 25 to only accept encrypted connections but am not having any success.  We have an existing root certificate (owa.redwoodit.com) that we use for RPC and Outlook Web Access.  I installed that certificate to the SMTP virtual connector checked the Require Secure Channel check box and set the Authentication to Basic and Require TLS encryption.  I setup an Outlook 2003 client to connect but I am getting the following error "establishing an encrypted connection to your outgoing (SMTP) server failed".  Any help or suggestions would be greatly appreciated as I am stumped on where to go from here.
0
Comment
Question by:deanavey
[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
  • 2
7 Comments
 
LVL 104

Accepted Solution

by:
Sembee earned 250 total points
ID: 18859085
If you have email coming in from the spam company coming in on a different SMTP virtual server then the simple fix for this problem is disable anonymous access to the port 25 SMTP virtual server. As long as your users authenticate when sending (which they should be doing anyway) they will be able to send their email correctly.

Simon.
0
 

Author Comment

by:deanavey
ID: 18859367
If I do that the users will still be sending thier user names in clear text.  Was wanting to make secure things up while making the change.
0
 
LVL 104

Expert Comment

by:Sembee
ID: 18859404
Is the name the users are entering in to the SMTP server settings on their clients the same as on the certificate?

Simon.
0
Edgartown IT Case Study

Learn about Edgartown's quest to ensure the safety and security of the entire town's employee and citizen data. Read the case study!

 

Author Comment

by:deanavey
ID: 18859577
Yes.  
0
 
LVL 23

Expert Comment

by:Stacy Spear
ID: 18859844
Is the TLS server and client ports matching?
0
 

Author Comment

by:deanavey
ID: 18860165
Yes they are on the same ports.
0
 

Author Comment

by:deanavey
ID: 18881683
I was able to find a work around.
0

Featured Post

Free Tool: IP Lookup

Get more info about an IP address or domain name, such as organization, abuse contacts and geolocation.

One of a set of tools we are providing to everyone as a way of saying thank you for being a part of the community.

Question has a verified solution.

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

A list of top three free exchange EDB viewers that helps the user to extract a mailbox from an unmounted .edb file and get a clear preview of all emails & other items with just a single click on mailboxes.
Unified and professional email signatures help maintain a consistent company brand image to the outside world. This article shows how to create an email signature in Exchange Server 2010 using a transport rule and how to overcome native limitations …
To show how to create a transport rule in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.: First we need to log into the Exchange Admin Center. Navigate to the Mail Flow >> Rules tab.:  To cr…
how to add IIS SMTP to handle application/Scanner relays into office 365.

739 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