Windows Server 2008 Server Core Installation. Jorge A. Ovando Zalapa. 28 May 2010
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1 P a g e 1 Creating a Request, Installing and Binding a 3 rd Party SSL Certificate: Windows Server 2008 Server Core Installation Jorge A. Ovando Zalapa 28 May 2010
2 P a g e 2 Creating a Request, Installing and Binding a 3 rd Party Certificate: Windows Server 2008 Server Core Installation Purpose: The aim of this document is to provide step by step procedures on creating a certificate request, installing and binding a 3 rd party SSL certificate on a Windows Server 2008 Server Core installation system. This document assumes that you have already installed IIS 7.0 and enabled IIS Remote Management. Requirements: IIS Manager IIS Management Console Remote Desktop SSL Certificate Preparations: 1. Turn on IIS Management Console on the PC that you will use to administer the server a. Control Panel > Programs > Programs and Features > Turn Windows features on or off b. Expand Internet Information Services > Web Management Tools, enable IIS Management Console 2. Download and Install IIS Manager a Remote Desktop into your Windows Server 2008 Server Core installation system Creating a Certificate Request: 1. Create a folder on your C: drive and name it temp 2. Create a request.inf file and place it in the temp folder a. The request.inf should look like this for a web server certificate: [Version] Signature="$Windows NT$" [NewRequest] Subject="C=US,S=YourState,L=YourCity,O=YourCompany,OU=YourOU,CN=Servername.domain.com" PrivateKeyArchive=FALSE Exportable=FALSE UserProtected=FALSE MachineKeySet=TRUE ProviderName="Microsoft RSA SChannel Cryptographic Provider" ProviderType=12 UseExistingKeySet=FALSE
3 P a g e 3 RequestType=PKCS10 ;HashAlgorithm=sha1RSA KeyLength=2048 KeyUsage = 0xF0 ; Digital Signature, Key Encipherment, Nonrepudiation, Data Encipherment KeySpec=1 [EnhancedKeyUsageExtension] OID= ; Server Authentication 3. Create CSR a. You can create the CSR with this cmd: certreq -new c:\temp\request.inf c:\temp\certrequest.txt (Paranormastic, 2010) Installing SSL Certificate: 1. Once you receive your SSL certificate save it to c:\temp on the Server Core system 2. Enter this cmd: certutil -addstore my c:\temp\certname.cer (name of your certificate) Verifying Installation: 1. Enter this cmd: certutil -viewstore my a. The Windows Security window should come up b. Select the certificate that you just installed and click on the Click her to view certificate properties link
4 P a g e 4 c. Verify that a key appears under the Valid from field 2. If that key does not appear then you will need to re-associate the private key a. Go to the Details tab on the Certificate Details window b. Go to the Serial number field and take note of the serial number c. Close the Certificate Details and Windows Security windows d. Enter this cmd: certutil -repairstore my serialnumber (Enter serial number obtained from the Details tab) e. Verify that the private key is associated by using the previously outlined verification process. f. You can also enter this cmd: certutil -store my serialnumber (The last line should read Encryption test passed) Binding Certificate 1. Now that the certificate is installed you can assign the certificate to your website using IIS a. Open IIS Manager, create a connection to the server that you installed the certificate on and connect to your server b. Under Sites, select the site to be secured with SSL c. From the Actions menu, click on Bindings. This will open the Site Bindings window
5 P a g e 5 d. In the Site Bindings window, click Add... This will open the Add Site Binding window e. Under Type choose https. The IP address should be the IP address of the site or All Unassigned, and the port over which traffic will be secured by SSL is usually 443. The SSL Certificate field should specify the certificate that you installed f. Click OK g. Your SSL certificate is now installed, and the website configured to accept secure connections (digicert.com, 2010)
6 P a g e 6 References Paranormastic. (2010). How to make a certificate request on a windows server core vm. Retrieved from /Q_ html Digicert. (2010). How to install your ssl certificate to your windows 2008 server. Retrieved from
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