Tuesday, 22 November 2016

Manually (painfully) generating a server certificate for LDAPS on Server 2003.

This is a bit of an odd one - as this process can be automated - but if you like me - prefer to do this manually I have documented the steps (briefly) below.

Firstly add the CA role by going to 'Add and Remove Programs' from the control panel and selecting the 'Add/Remove Windows Components' and ensure that 'Certificate Services' is checked as well as ensuring that the 'CA Web Enrollment' feature is installed as well (click on the details button.)

Now lets create a certificate template for this purpose - so go to:

mmc.exe >> 'Add Snapins' >> Certificate Authority >> Right-hand click on the 'Certificate Templates' node and select 'Manage.' We will now duplicate an existing template (as required) - so right-hand click on 'Domain Controller Authentication' and hit 'Duplicate Template.' I then named my new template: 'Domain Controller Authentication Manual' and in the 'Subject Name' tab ensure 'Obtain from Active Directory' is selected. In the 'Security' tab ensure that only the 'Domain Admins' user group has the enroll permissions and in the 'Extensions' tab that 'Server Authentication' (OID: and finally in the 'Request Handling' tab ensure that 'Allow private key to be exported' is ticked.

Click apply / OK etc. and finally hit OK on the new template form to create the template.

Then on the CA authority snapin - right-hand click the 'Certificate Templates' node >> New >> 'Certificate Template to Issue' and select the relevant template. NOTE: In my case the template wasn't present so I added the template via CLI:

certutil -SetCAtemplates +DomainControllerAuthenticationManual

Restart certificate services.

Now we need to ensure that the FQDN of the server is within the trusted sites zone in IE e.g.:


(If you do not add the FQDN to the trusted zone you will get an 'access denied' message when attempting to generate the certificate - which can be quite misleading!)

and then browse to:


and enter your domain credentials.

Then from the task list select 'Request a certificate' >> 'Advanced certificate request' >> 'Create and submit a request to this CA'. At this point you should be prompted to install an active-x control - ensure this is installed before proceeding.

Select the 'Domain Controller Authentication Manual' template and ensure that the subject names matches that of the DC you wish to setup LDAP for and also ensure 'Store certificate in the local computer certificate store
' is ticked and finally hit submit to import the certificate into your computer's certificate store.

We should also ensure that the "HTTP SSL" service has started and will be started automatically at boot!

and then test our ldaps connection:

cmd.exe ldp

and connect to the server using the DC's FQDN (the IP will NOT work) e.g.


For more information about troubleshooting ldap over SSL see below:



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