Secure Authentication between Zimbra and AD

Revision as of 00:55, 24 October 2016 by Teodor Vizirov (talk | contribs) (Secure Authentication between Zimbra and AD (self-signed certificate))

Secure Authentication between Zimbra and AD (self-signed certificate)

   KB 23061        Last updated on 2016-10-24  

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How to configure authentication with Active Directory using SSL.


Before everything else, make sure that the non-ssl (port 389) AD authentication is working, by following that article.


1. Review the following article to familiarize yourself with the authentication with AD from Zimbra side in AdminUI. The only difference is that in the "Active Directory Settings" , the "Use SSL:" tick box is selected:

3 ad ssl.JPG

2. Convert the zimbra CA to .der, and copy it to the DC:

cd /opt/zimbra/ssl/zimbra/ca
openssl x509 -in ca.pem -outform der -out ad.der
  • Use tools such as WinScp to copy the /opt/zimbra/ssl/zimbra/ca/ad.der file to the DC.

3. Install the Zimbra certificate authority (CA) on the domain controller:

  • Start->Run > Type mmc > Right click on it > "Run as Administrator". This will open the Microsoft Management Console.
  • Click "File" > "Add/Remove Snap-In..." to open the "Add Standalone Snap-in" dialog.
  • From the Available snap-ins on the left, select "Certificates" and press "Add".
  • Select "Computer account" and press "Next".
  • Select "Local computer" and press "Finish"
  • Click "Ok" to close the "Add/Remove Snap-in" dialog.

Once the "Certificates snap-in" is open, click on the "Certificates" node under "Trusted Root Certification Authorities". Right-click on the "Certificates" node, select "All Tasks" -> "Import...", and import the Certificate Authority (in my case "ad.der") you copied from Zimbra. Accept the default location: Trusted Root Certification Authorities

4 ad ssl.jpg

4. Create a csr. For this purpose we will use Microsoft's certreq utility. To generate csr, we need to create a *.inf file. Below is a sample *.inf file you ca use.

  • Open a text editor (Notepad) and paste the following text into the file. Make sure no CR/LF character is added to the "Subject =" line when you copy and paste the text. Remove if any:

;----------------- csr.inf -----------------

Signature="$Windows NT$" 


Subject = ", OU=Organizational_Unit, O=Organization, L=City, S=State, C=Country" 
; Replace with the FQDN of your AD server's FQDN.
; Replace the remaining Subject attributes.
KeySpec = 1 
KeyLength = 2048 
HashAlgorithm = SHA256
Exportable = TRUE 
MachineKeySet = TRUE 
SMIME = False 
PrivateKeyArchive = FALSE 
UserProtected = FALSE 
UseExistingKeySet = FALSE 
ProviderName = "Microsoft RSA SChannel Cryptographic Provider" 
ProviderType = 12
RequestType = PKCS10 
KeyUsage = 0xa0 


OID= ; this is for Server Authentication 

  • Update the Subject attributes with appropriate values. For example: The FQDN must be the name of the AD server.

4. Once you have a inf file, generate a Certificate Signing Request (CSR) using certreq. Open CMD and type:

certreq -new ad.inf ad.csr  

5. Sign the certificate. Copy the csr to the ZCS server and run as root:

openssl x509 -req -days 365 -in ad.csr -CA /opt/zimbra/ssl/zimbra/ca/ca.pem -CAkey /opt/zimbra/ssl/zimbra/ca/ca.key  -set_serial 01 -out ad.crt

That will create a file ad.crt. Copy the file back to the AD server.

6. Accept the Certificate After the ad.crt file has been copied to the AD server, run the following command to accept it, using the "certreq" utility:

certreq -accept ad.crt

This will accept the cert in the Windows certificate store and it will be available to those services and products that make use of the Windows certificate store. These products include but are not limited to: IIS, Exchange, Active Directory (LDAPS), Terminal Services and Microsoft Management Console (MMC).

7. Install the certificate.

From Step 3, open the "Certificates snap-in", expand the "Certificates" node under "Personal". Right-click on the "Certificates" node, select "All Tasks" -> "Import...", and import the "ad.crt".

5 ad ssl.jpg

8. Restart AD server


To make sure the SSL is working, we can use ldp.exe. Click Start> Run > type ldp.exe and open it. At top left, click on "Connection" > "Connect...".

Verified Against: Zimbra Collaboration 8.6, 8.5, 8.0 Date Created: 31/05/2016
Article ID: Date Modified: 2016-10-24

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Wiki/KB reviewed by SME1 SME2 COPY EDITOR Last edit by Teodor Vizirov
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