Server's certificate chain has expired or is not yet valid

Posted on 2009-04-06
Medium Priority
Last Modified: 2012-05-06
I updated our SSL Cert for our Exchange 2003 server back in January. I believe the current certificate was due to expire yesterday (April 5th, 2009). As of this morning, I am receiving the following message on Entourage clients which have been configured with the option "This LDAP server requires a secure conection(SSL)". I do not encounter certificate errors when I connect to the Exchange server via OWA. I have verified on my exchange server that the current certificate installed for the 'Default Web Site' is valid, it expires on April 5th, 2011. Is there perhaps another location in which I missed updating the cert? Any info would be greatly appreciated. I am attaching a screen cap of the error message which Entourage is producing.
Question by:sgs521
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
  • 5
  • 2

Expert Comment

ID: 24081096

How is this client connecting to the server?  If POP/IMAP, have you made sure the new certificate is installed on those services?


Author Comment

ID: 24081134
The client connects as an exchange client, which in my limited understanding of how Entourage actually talks to exchange, I think is over http. There's a configuration option in the account setup that specifies the account is on exchange, then I have to enter both the exchange server and ldap server, which is the same server address. We don't have anyone who is using pop, smtp or imap directly from the email client in our environment.
Is Your AD Toolbox Looking More Like a Toybox?

Managing Active Directory can get complicated.  Often, the native tools for managing AD are just not up to the task.  The largest Active Directory installations in the world have relied on one tool to manage their day-to-day administration tasks: Hyena. Start your trial today.


Author Comment

ID: 24081856
Thanks strung, the first link http://www.askdavetaylor.com/install_root_certificate_with_microsoft_entourage.html seemed to fix this. Just really odd that it had been working before this when we'd never installed the cert client side. Going to do more testing across other workstations before I accept as solution, but it looks like that may be the one.
LVL 53

Expert Comment

ID: 24082230
Glad to be of help


Author Comment

ID: 24087753
An update, I returned to the office this morning, booted up my laptop, launched Entourage and received the error again. So it looks like perhaps installing the cert client side only temporarily fixed until reboot. I'm thinking there's still something I've missed when updating the secure cert on the exchange server. The only way to repeatedly duplicate the issue is by turning on the "this ldap server requires a secure connection" option under account settings in Entourage. Is there another location that the certificate needs to be installed within Active Directory to secure it's ldap communication?

Author Comment

ID: 24087764
Also as an update, on the configuration of the exchange server, this was put in place prior to my arrival, but it was configured with AD and Exchange on the same server.

Accepted Solution

sgs521 earned 0 total points
ID: 24132512
Corrected this issue by removing and re-adding the certificate, rebooted the server. 5 days now and no further incidents of the ssl error client side.

Featured Post

Independent Software Vendors: We Want Your Opinion

We value your feedback.

Take our survey and automatically be enter to win anyone of the following:
Yeti Cooler, Amazon eGift Card, and Movie eGift Card!

Question has a verified solution.

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

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...
There are times when we need to generate a report on the inbox rules, where users have set up forwarding externally in their mailbox. In this article, I will be sharing a script I wrote to generate the report in CSV format.
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…
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

764 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