How to Issue a SAN Certificate to Exchange Server 2010 from a Private Certificate Authority

Comments

1. 

   SJ04 25 Jul 2016 Reply

   Hi Paul,

   I have followed this guide to generate the Certificate from Private CA, I have also sucessfully Exported this Certificate to Exchange server and as well as assigned the Services to the certificate also.
   all seems to be working fine and my Internal User doesnt even realize any changes. but today i have just check the properties of my Certificate and in the certificate information, it only shows,

   This Certificate is intended for the following Purpose(s):
   > Ensure the identity of a remote computer.

   is it correct or i have exported the wrong certificate.

   thanks
   Please help

2. 

   Bhanuprakash Chakivela 28 Jun 2016 Reply

   Very useful article

3. 

   Thad 16 Dec 2015 Reply

   Hello Paul,

   I have read a few of your articles to help understand Exchange better being new to it. I have a question and you may have to explain it to me like I’m 5. I am trying to deploy O365 in our environment and running into road blocks with Exchange, DNS and certs. I inherited Exchange and the setup looks different that what has been described in most books. It looks like we have the same issue you are describing but unsure of how to resolve because of the slight differences. Ok we are a gov agency ( I changed info for obvious reason):

   internal domain is: citizens.gov
   mail server is: mail.citizens.gov
   Our MX record is mapped to mail.citizens.state.gov
   Exchange cert is owa.citizens.state.gov — no SANs attached.
   We have 2 DNS Forward Lookup Zones: citizens.gov and citizens.state.gov

   We have a few problems:
   1. A name mismatch error certificate error recently starting appearing saying mail.citizens.gov is not on certificate.

   2. I need to reconfigure my certificate to include all necessary SANs for O365. Not sure what all should be included. Should I include:

   autodiscover.citizens.gov, autodiscover.citizens.state.gov, owa.citizens.state.gov, mail.citizens.state.gov, mail.citizens.gov

   3. This has stalled the O365 migration as DNS and certs have to be set up properly.

   In regards to issue 1, I believe that issue will be resolved once I get the certificate issue resolved. However I am not sure if I should put/able to put the internal names on the cert like (anyname).citizens.gov. Should i resolve this with DNS if so what records would I need?

   I have to generate a new cert with SANs. What should be included? do I need to put

4. 

   Clay 4 Oct 2014 Reply

   Thanks! This is exactly what I needed.

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6. 

   Troy 31 May 2014 Reply

   Hey Paul,

   Quick question. Have you ever seen a situation where you issue an SSL cert from a CA server on MS Server 2008 with the SAN information, but then once you try to access the FQDN from a web browser you get an error. On the bad cert there is no more SAN field and the error message is “mismatched address?”

   Anything would help!!

   1. 

      Paul Cunningham 31 May 2014 Reply

      No SAN info on the cert? Perhaps the wrong cert is being used. Have you checked that the correct cert has been enabled in Exchange?

7. 

   Sandro Alves 10 May 2014 Reply

   Paul ,

   I have one just like it ( http://faragesolutions.files.wordpress.com/2013/04/proxy.jpg?w=650 ) scenario . Using two Exchange , only one of them is accessed as a proxy .

   In Exchange that is facing internet , I use a digital certificate with the public domain ( webmail.name.com ) and my OWA is configured to ( External: webmail.name.com ) and (Internal : webmail.name.com ) .

   You Exchange that are not face to internet , OWA is configured to ( External: empty) and ( Internal : servername.local ) . This Exchange user when connecting with Outlook client is generating validation error name ( servername.local ) , because as I’m using the same Exchange certificate that is facing internet . So the audience is trying to validate the certificate name that is not registered as an alternative name.

   question : the exchange that is not facing the internet, I need to use the same public certificate that is in exchange that is facing the internet? or can I just use an internal certificate?

   Thank you.

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9. 

   Jamie 8 May 2013 Reply

   Thanks for this Paul!
   I was getting a bit confused as to why after completing the previous request I had (using a technet guide) my cert was disappearing from Exchange.
   However – Your guide was much clearer, and worked first go!

10. 

    reda_boutbicha 7 Mar 2013 Reply

    Hello
    I set up two CAS servers in NLB mode
    cas1.domain.local
    cas2.domain.local
    and the name of NLB: mail.domain.local
    Do I put the netbios name server if the certificate SAN, or I will just put the name of nlb: mail.domain.local
    thank you

    1. 

       Paul Cunningham 7 Mar 2013 Reply

       The intro section of this article explains which names to include. I’d recommend you read that.

       The NLB cluster name doesn’t need to be included. Neither does the CAS Array name (which is not necessarily the same as the NLB cluster name, though they can be the same). The names that need to be included are any that clients will be connecting to over HTTPS.

11. 

    Dimo 12 Feb 2013 Reply

    Great post again Paul.

12. 

    David 22 Jan 2013 Reply

    I have a certificate issued by Verisign that will be expiring soon. Since I have no external facing services there doesn’t seem to be any point in paying for renewal. Is it safe to simply allow the existing cert to expire and issue one from my CA to “replace” it, following the above instructions?

    1. 

       Paul Cunningham 22 Jan 2013 Reply

       Don’t wait for it to expire. If it expires clients will begin showing certificate validation errors to your end users. You should replace it before it expires.

       Yes, if you choose to go with a private CA you can follow the instructions above to provision the cert, then make sure you also enable it for the services previously associated with the old cert.

13. 

    Mike Joseph 28 Dec 2012 Reply

    Hello, I followed this article because my client with Exchange 2007 has an internal domain name of cjn.com but they do not own cjn.com so I cannot get a UCC cert from GoDaddy to cover the FQDN of their exchange server. Consequently, users get an SSL error every time the open Outlook.

    I installed a Certificate Services server and followed your article. Now, users no longer get the SSL error when they launch Outook, but IE complains about the cert when they go to OWA:

    “The security certificate presented by this website was not issued by a trusted certificate authority.”

    Is there anyway around this? Once again, this is Exchange 2007 not 2010.

    Thanks!

14. 

    NickRTT 7 Dec 2012 Reply

    Thanks Paul, all your articles make my life with exchange bliss m8

15. 

    Pavan Segal 30 Nov 2012 Reply

    Hi
    I would like to follow the steps mentioned in the article above to issue a new certificate from my own server…
    My Exchange server is a member server. Can I install the AD Certificate Services on the Exchange Server (eg a member server) or is it better to install the Certificate server on the DC ?

16. 

    Exchange User 12 Oct 2012 Reply

    hi Paul,
    thanks for your help, now the certificate is not self signed..that’s fine but it apears with in red meaning that the server coundn’t find the revocation list, wich i importe from my CA and install it on the server BANK certificat but still havin’ the problem
    regards

17. 

    Exchange User 9 Oct 2012 Reply

    hi,
    i have two DCs and a domain wich my user’s trust :DC1, DC2 i found a CA on the DC2 but my exchange organisation is on a diffrent domain with two mailbox on DAG and CAS Hub and two DCs but no CA on this domain
    my problem is that when i tried to generate a certificat on my CAS as shown on steps and sign it on the CA that my user’s trust, the certificat request is always keeping peending and self signed.

    MY ORGANISATION:
    DC1
    DC2 with CA on it

    EXCH_DC1
    EXCH_DC2
    EXCH_CAS
    EXCH_MBOX1
    EXCH_MBOX2

    1. 

       Paul Cunningham 9 Oct 2012 Reply

       The certificate request will remain pending until you download it from the CA and complete the pending request.

       1. 

          Exchange User 10 Oct 2012 Reply

          i did it and on may way for that it was all “green” it seems to be correcte, but unfortunetly the certificat is still peending and self signed 🙁

18. 

    Kiran 4 Sep 2012 Reply

    i have 2 physical separate sites as two child domains US.acme.com and the other as IN.acme.com. The user base is present in these two domains. The exchange is installed on the root domain (Acme.com).Now i want to go with one single certificate for exchange 2010(not the wild card). I want to ensure that US users connect to the US Exchange(CAS+HT+MB) and India Users connect to the India EXchange(CAS+HT+MB). The question is should i have two separate autodiscover entry in the SAN or is it possible or necessary? And if it only requires one entry, i need to understand how the autodiscovery works for a user who sits externally to connect to the mail server. In the sense what mechanism takes place to ensure that the user connects to the right CAS server.

    1. 

       sharpwaves 12 Sep 2012 Reply

       Hi,
       I am in the same situation.
       Certificate MisMatch OR Outlook …. proxy server…Error 8, works fine when connect through VPN or internal LAN. IMAP & POP is working fine.
       Exchange Test says the same thing.
       The site has SBS 2011, Exchange 2010, Outlook 2010 external client and NO Public SSL yet.
       I realised there is no entry for Autodiscover.EXTERNALDOMAIN.NAME (e.g. autodiscover.contso.com) on the certificate created by SBS. How would I add a domain to current certificate?
       I am unable to issue a new certificate as certsrv is not loading.
       Strangly, outlook is pulling all the information from Server externally.
       Any experience ?????

       1. 

          Paul Cunningham 17 Sep 2012 Reply

          Providing the exact error message in full would be a big help here.

19. 

    Romain 1 Sep 2012 Reply

    Hi Paul, thank you or this very valuable article.
    Some users would like to access to Outlook Web Access from a computer ouside of the domain and dns.
    So they access by ipaddress, not by the fqdn: https:///owa.
    It works fine but they still have certificate error , even when i put the ipaddress as an Altrnative Name (SAN).
    But if they update their host file and access to OWA by he fqdn it works.
    What could be the problem? Is it possible to access to owa url by ipadress without having certificate issue?
    hanks

    Romain

    1. 

       Paul Cunningham 1 Sep 2012 Reply

       You should create a public DNS record for OWA and have your users use that.

       Note that recent changes in the rules governing how SSL certs are issued means you won’t be able to get certs for IP addresses or short names (eg “owa”) in the very near future.

       Better off doing it the right way right from the start 🙂

20. 

    fazlin 29 Aug 2012 Reply

    what can i do to start useing Outlook for remote users and other servides which require trusted certifficates

21. 

    fazlin 28 Aug 2012 Reply

    I successfully created a new Exchange 2010 SP2 certificate. Downloaded and installed the certificate as per GoDaddy kb. After I had successfully completed the “Complete Pending Request” I dont see the new certificate in EMC. The only certificate I can ses is the first “Microsoft Exchange” certificate which gets automaticly installed while installing MS Exchange. My Exchange 2010 SP2 runs on second 08 R2 Ent server.

    1. 

       Paul Cunningham 3 Sep 2012 Reply

       So in the EMC you created the certificate request, and were able to see the pending certificate request, but then it just disappeared when you completed it?

       1. 

          Fazlin 4 Sep 2012 Reply

          thats correct, I can still see the first certificate “Microsoft Exchange” which is the self signed certificate but not the one which I had created and used it to purchase a Godaddy cert and later cant find in EMC after completing pending tasks.
          This is my fifth exchange 2010 deployment this year but first with SP2 and I had never had this issue in any version of exchange earlier

          1. 

             Paul Cunningham 4 Sep 2012 Reply

             Interesting.

             Run MMC and add the Certificates snapin for Local Computer, and see if you can see the cert in the Personal/Certificates store there. If not, its possible it has somehow been deleted.

          2. 

             John 1 Dec 2012 Reply

             I just experienced the same problem as Fazlin. I looked here -> “Run MMC and add the Certificates snapin for Local Computer, and see if you can see the cert in the Personal/Certificates store there.”

             I have done this and can see the default Microsoft Exchange cert for Server Authentication, as well as my new cert for Server and Client Authentication. Any hints on what has happened here or how I can resolve this?

          3. 

             Kevin 12 Jan 2013 Reply

             Same problem here. I can’t believe it just disappeared!!! no error messages or anything. As John says it is in the Personal cert store along with the self signed original exchange one. I guess the only non standard thing about my set up is that I am in the process of migrating from exchange 2007 to 2010. Any ideas on how to get this cert back into exchange so I can assign services to it??

          4. 

             James 15 Feb 2013 Reply

             Hi, great article. Just in case it helps anyone, I had this exact problem. However it was my fault for not selecting ‘Web Server’ when I requested the certificate.

          5. 

             Mike 2 Nov 2015 Reply

             I had this exact issue too, following the go daddy KB. when importing the cert into the ” intermediate root certification I change the file search to *.* and I clicked on the .cer extension, then went to EMC and then picked it again, IE the .cer extension. The proper way is to pick the PK7 extension of the certificate files you get when importing the certificate in certificate snapin, and then the .cer when in the exchange server. Otherwise, it literally just… poof… gone. You will have to REKEY the cert because you will not have the “finish pending request” in exchange. Hope that helps everyone. p.s. I don’t know much about this, I just thumble my way through 🙂

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26. 

    Amit 26 Jun 2012 Reply

    Hi Paul,
    Can you tell me how to generate and assign certificate for multiple CAS server exchange 2010. Further i would like to know if i generate certiifcate from private CA and assign it to CAS server is it ok

    CAS server name CAS1 & CAS2
    domain name which will be used for all the services is : mail.domain.com

    1. 

       Paul Cunningham 27 Jun 2012 Reply

       Hi Amit, you can do it a few different ways. Either generate a separate cert for each server, or do one cert request that includes all of the CAS server FQDNs in it. You can then export the cert from the first server you install it on and import it into the other(s).

27. 

    Lukman 23 Jun 2012 Reply

    Hi paul.
    i bought a SSL certificate from verisign for my exchange 2010 and it working fine when i use owa but am having a certificate mismatch error every time i open my outlook 2010 form computer that is joined to the domain

    1. 

       Paul Cunningham 27 Jun 2012 Reply

       Hi Lukman, so the certificate warning box you see pop up specifically says the names don’t match?

       Did you buy a SAN cert (ie multiple names) or a single-name SSL cert?

       1. 

          LukmaN 28 Aug 2012 Reply

          Hi Paul,
          the certificate i bought was a single-name SSL cert.
          but the warning i see is only on outlook

28. 

    Mike 15 Jun 2012 Reply

    Can a Windows 2003 Standard edition CA issue certificates with SAN? For our test environment we’d like to issue the certificates from our internal CA but it’s based on Windows 2003 Standard and I have not been able to find this information. Is a Version 2 template required to issue a certificate with a SAN or can Version 1 templates work too?

29. 

    Rick 8 Jun 2012 Reply

    Hello Paul;

    Just looked at this article which was great to learn how to make an exchange certificate. Just to add in the note for this article for how to find the output a certificate request that was made in the MMC exchange console is the following:

    1) Right-click the exchange certificate file which is the .reg extension.
    2) select open with or open
    3) open using notepad and there you will find all the information per example below:
    —–BEGIN NEW CERTIFICATE REQUEST—–
    xC7C9Yk06onHypefiz+uTubNULjKBKdtJiyesj6hakyG1tFddsvv6yqwjtAefyVZ
    vYWbkSJiXTwALuOrePlt3wGa12ZxqYwl2Mf98gdb2fTq2M6TosPE0PIxoDZvBzV2
    IHZxAgMBAAGgggHQMBoGCisGAQQBgjcNAgMxDBYKNi4xLjc2MDAuMjBlBgkrBgEE
    AYI3FRQxWDBWAgEFDBtFWDMuZXhjaGFuZ2VzZXJ2ZXJwcm8ubG9jYWwMEEVYQ0hT
    RVJWUFJPXEVYMyQMIk1pY3Jvc29mdC5FeGNoYW5nZS5TZXJ2aWNlSG9zdC5leGUw

    —–END NEW CERTIFICATE REQUEST—–

    From: Rick.C

30. 

    uwedadmin 25 Jan 2012 Reply

    Hi, everybody! i need your help, Powershell show this error when runing with “certutil -setreg policyEditFlags +EDITF_ATTRIBUTESUBJECTALTNAME2” command: Certutil: -setreg command failed: 0x8007000d, Certutil: The data is invalid

    How i can fix this?

    1. 

       Paul Cunningham 28 Jan 2012 Reply

       Are you copy/pasting the command from a web page, or typing it out yourself?

       1. 

          uwedadmin 29 Jan 2012 Reply

          No, type it out myself…. but on command promt cetutil is runing without troubles, now, another problem, Exchange SA service is not running automatically and test -servicehealth command shows Mailbox Server Role: False, how i can fix this problem?

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33. 

    Miroslav Gree 17 Oct 2011 Reply

    Hello, thanks for your articles about SAN certificates. I have a Q about SAN names. In the real world, SAN certificate for Ex 2010 must includes these names in cert : in the case of internal and external domain

    – server FQDN (server.company.local)
    – name for webaccess for external users (webmail.mycompany.com)
    – name for autodiscover (autodiscover.mycompany.com)
    – name for webaccess for internal users (webmail.mycompany.local)

    And netbios name of server (for example “server”) is needed too ? I have read many artciles, some says you do not have to include netbios name, some articles says you have to include the netbios name.

    So what about netbios name in the SAN ?

    Thanks for reply.

    1. 

       Paul Cunningham 23 Oct 2011 Reply

       Netbios would be needed if you plan to have your internal users hitting OWA (for example) by using the server’s Netbios name. As long as they’re hitting the FQDN then no need to include the Netbios name.

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35. 

    Rob Gibson 30 Sep 2011 Reply

    What about the private key. I thought that had to be exportable when you did an Exchange Self Signed Certificate?

    1. 

       Paul Cunningham 1 Oct 2011 Reply

       This article doesn’t describe a self-signed cert, it describes how to issue a cert to Exchange from a private CA.

36. 

    Manjula 15 Sep 2011 Reply

    i have installed En root CA on my Additional AD (windows 2008 r2), do you recommend it?
    i just install Exchange 2010 sp1.
    And i failed to issue certificate by the CA console and Web enroll, in the web enroll i cant select “web server” in certificate template. only contain “user” and “basic EFS”.
    i had tried by issuing certificate request by Exchange 2010 EMC and EMS.

    What can i do to over come this?

    1. 

       Paul Cunningham 20 Sep 2011 Reply

       You can use your own CA if you like it just means non-domain members will not trust the CA until you deploy the root certificate to them.

       If you’re not seeing the web server template I’d say your account doesn’t have permissions to request that type of cert.

37. 

    sam 19 Aug 2011 Reply

    Hi again, I’ve applied the new SAN certificate (created a new CA on the CAS with Windows Server 2008 R2 and issued a certificate) and assigned services (IMAP/POP/IIS/SMTP) , all worked fine for my domain joined PCs but a pc with Outklook 2010 says “the security certificate was issued by a company you have chosen not to trust “.
    Can you help with this? Thanks.

    1. 

       Curtiss 19 Aug 2011 Reply

       your machines or users with outlook 2010 have to trust the publisher of the certificate. you can use group policy to publish the CAS’s “root certificate” to the “trusted publishers” certifcate store. outlook 2007 did not throw this error for self-signed or untrusted certificates. if the problem pc is not a domain pc, you can manually put the root certificate into trusted publishers on that pc with the Certificates mmc console.

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40. 

    Curtiss 10 Mar 2011 Reply

    i don’t get the “begin new certificate request”/”end new certificate” text output after i run the new-“exchangecertificate … -generaterequest” command. i just get a thumbprint.

    Thumbprint Services Subject
    ———- ——– ——-
    C527BEEE14788799C6C602AAF7D6DEBFDA8509D0 …… CN=sisexcp9.student.dom

    i ran the command on an exchange 2010 sp1 server running on 2008 r2.

    1. 

       Paul Cunningham 10 Mar 2011 Reply

       Hi Curtiss, if you’re having problems with the shell try using the console to generate the cert request instead. Steps are here:

       https://www.practical365.com/configure-an-ssl-certificate-for-exchange-server-2010

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42. 

    Raffaele Marmiroli 19 Jan 2011 Reply

    I was stuck with the Certification server policy. That worked also for Windows Server 2008 CertSrv.
    Thank you. I’ll reference this doc in my blog.

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