[Webinar] Streamline your web hosting managementRegister Today


Unrecognized certificate error

Posted on 2010-04-06
Medium Priority
Last Modified: 2012-05-09
Our mail server name is server16C. MAIL is the alias name of server16C.

Users use mail.ourdomain.com/exchange to access OWA in and out the company.

Users don't like to use server16C.ourdomain.com/exchange for OWA access.
Last year, we bought SSL certificate for MAIL.OURDOMAIN.COM. It worked,
but keeping showing unrecognized certificate error.

What is the solution? Do we have to buy certificate for SERVER16C.OURDOMAIN.COM?

Networksolutions.com said we need to buy 2 certificates to solve this problem,
one is inside, the other outside. Not quite understand their idea.
Question by:sjacct
LVL 15

Expert Comment

ID: 29963896

Author Comment

ID: 30215009
It is not "page contains secure and nonsecure items" warning.
LVL 51

Expert Comment

by:Steve Bink
ID: 30994651
What is the exact error when you browse to http://mail.ourdomain.com?
Simplify Active Directory Administration

Administration of Active Directory does not have to be hard.  Too often what should be a simple task is made more difficult than it needs to be.The solution?  Hyena from SystemTools Software.  With ease-of-use as well as powerful importing and bulk updating capabilities.


Author Comment

ID: 31315843
Can't remember what exact the error was. Its address bar showed pink color instead of green color.

I noticed someone mentioned aka multi-domain cert or SAN cert. Can anyone provide more info for this specific cert?

Thanks !
LVL 12

Expert Comment

ID: 32120763
I believe you are referring to a Unified Communicatiions Certificate (UCC). This is a bit more costly, but generally this is the simplest and supported solution for the problem you are seeing. Basically, a UCC allows you to define a primary FQDN, such as server16C.ourdomain.com, then specify alternate FQDN in the Subject Alternate Name (SAN). This makes the SSL certificate valid for those other FQDN.

We used a Comodo UCC as it is on Microsoft's official list of supported Exchange UCC CAs, but any UCC from a major CA should work. I followed the instructions here without any issue to install it:

Basically, a single standalone SSL cert is not going to work with multiple FQDNs on the same server.

Author Comment

ID: 32564957
Thank you, geowrian!

The problem right now is no one can tell me the right name of this certificate. I have talked to all major CA sales experts. No one can tell which is the one we need and how to use it.

Is this UCC same as SAN cert? In your link, it is Exchange 2007. We are using Exchange 2003. I can't find that Exchange Management Shell on 2003.

Let me find out what is this UCC and how it works.

Thanks again.
LVL 12

Expert Comment

ID: 32567842
A "SAN" cert is a multi-domain cert. Actually you could use a regular multiple domain cert, a wildcard cert, or a UCC. A multi-domain cert and a UCC both work via specifying alternate FQDNs in the Subject Alternate Name (SAN) section of the SSL certificate. A wildcard cert does not use the SAN section, but allows all subdomains. I wouldn't recommend using a wildcard cert for an Exchange server, but it should be possible. A UCC or other mult-domain cert should work fine.

Generally, you want an SSL cert on an Exchange box to cover the systems with the following FQDNs (ignoring those you do not host on the server):
1) The autodiscover record (free/busy information, Out-of-Office, etc.)
2) Any POP server DNS records
3) Any IMAP server DNS records
4) Any SMTP DNS records
5) Any OWA DNS records

My mistake on the Exchange 2007 document - this is the first time I saw Exchange 2003 mentioned in the question, and it makes a huge difference. Exchange 2007 has many tools available as well as a simple PowerShell command to generate the CSR with the SANs in it. It is much more painful in Exchange 2003, unless you use a wildcard cert, which is considerably more expensive. Unfortunately, I have not done it myself in Exchange 2003, so all I can give you is what I believe will work. Basically, it uses the certreq.exe application to generate the CSR with the SANs in it, then you manually import it into IIS:

The usage of certreq is here:

Once you have a CSR, send it to the CA (GeoTrust, Comodo,etc.) to get the SSL certificate. Then open mmc and add the Certificates snap-in (on the Local Computer account). Go tot he Personal certificates and import the SSL certificate. This makes the SSL certificate available to IIS.

Now open up IIS Manager -> right-click your website -> Properties -> Directory Security -> Server Certificate... -> Next -> Replace the current certificate -> Choose the newly-generated SSL cert in the list -> next -> Finish. This should start serving the SAN-enabled cert immediately. If not, stop/start IIS just to be safe. Confirm i a browser that it is using the new SSL cert and have the Subject Alternate Name field with all the secondary FQDNs in it.

I wish I could tell you more, but without having done it myself, I'm not going to be much more of a help in Exchange 2003.

Author Comment

ID: 32709404
To be honest, I'm still confused. Verisign contacted us recently. their solution is using 2 certs, one for mail server, one for OWA. I don't know if it is the right way before we can do real testing. The issue is no one can explain the mechanism of their method.

Accepted Solution

sjacct earned 0 total points
ID: 33121414
The problem is eventually solved.

We found an article, in Microsoft TechNet, "How to Simplify the Outlook Web Access URL".

To simplify the Outlook Web Access URL
1. Using the Internet Services Manager, open the properties for the Default Web Site.
2. Click the Home Directory tab, and then select A redirection to a URL.
3. In Redirect to, type /<directory name>, and then click A directory below URL entered. For
example, to redirect https://mail/ requests to https://mail/exchange, in Redirect to, you would
type /exchange.

We did it as the article suggested. Then, we bought a single domain certificate for

No more error, the result is simply what we expected.

Kind of disappointed, in Expert-Exchange, no one could give us this simple solution. It took us so long
to figure it out.
LVL 12

Expert Comment

ID: 33124085
I'm glad it worked out for you. However, that solution worked for now, but you may have some issues down the road, especially if you upgrade or grow. For one, OOA and other Autodiscover-based features may be a little funny due to the redirection. I'm not sure how regular Outlook clients in Exchange mode would react, either.

But I wish you the best and am glad it's worked out.
LVL 76

Expert Comment

by:Alan Hardisty
ID: 34203703
This question has been classified as abandoned and is being closed as part of the Cleanup Program.  See my comment at the end of the question for more details.

Featured Post

Will You Be GDPR Compliant by 5/28/2018?

GDPR? That's a regulation for the European Union. But, if you collect data from customers or employees within the EU, then you need to know about GDPR and make sure your organization is compliant by May 2018. Check out our preparation checklist to make sure you're on track today!

Question has a verified solution.

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

I am posting this in case anyone runs into similar issues that I did, this may save you a lot of grief: Condition: 1. Your NetBIOS domain name contains an ampersand " & " character.  (e.g. AT&T) 2. You've tried to run any Microsoft installation…
After a recent Outlook migration from a 2007 to 2010 environment, some issues with Distribution List owners were realized. In this article, I explain how that was rectified.
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…
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

590 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