How to Generate CSR on SBS 2008 / 2011?

If you’re still running Windows Small Business Server (SBS) 2008 or 2011, chances are you need to secure your websites, email services, or remote access with an SSL certificate. Before you can install an SSL certificate, you first need a Certificate Signing Request (CSR).

Think of a CSR like a passport application. You can’t get a passport without first filling out a detailed application that proves your identity. Similarly, you can’t obtain a trusted SSL certificate from a Certificate Authority (CA) without submitting a CSR.

The good news? Generating a CSR on SBS 2008/2011 isn’t rocket science. It just takes a few clicks, a bit of attention to detail, and knowing where to look. Let’s walk through it step by step.

Why a CSR Matters (And Why You Should Care)

Let us have a look at the answer to this question before we leap into the steps. Why does this matter?

• Trust: Your visitors are warned without the use of SSL. They can identify the padlock symbol with it and understand that they are safe.
• Data Protection: Sensitive information, such as logins, emails, and payments, is encrypted using the SSL system.
• Compliance: In various industries, encryption is mandated by regulations.
• SEO Boost: Google prefers secure websites in search results.

SSL cannot be overlooked by your business if it continues using SBS 2008 or 2011. The first step towards having that trust seal is a CSR.

Prerequisites Before You Start

Before generating your CSR, make sure you have the following ready:

• Administrator access to your SBS server.
• The fully qualified domain name (FQDN) you want the certificate for (e.g., mail.yourdomain.com).
• Company details (official business name, locality, state, country).
• A decision on the type of SSL certificate (Single Domain, Wildcard, or SAN).

Having this information upfront will save you from headaches later.

CSR Generation Steps for SBS 2008 / 2011

Step 1: Open the SBS Console

• Log in to your SBS 2008 or 2011 server.
• Click on Start > All Programs > Windows SBS Console.
• Wait for the console to fully load.

You might also be able to open the Exchange Management Console directly, but sticking with the SBS Console is simpler for most administrators.

Step 2: Navigate to the Certificate Request Wizard

• Inside the SBS Console, click the Network tab.
• From there, click Connectivity.
• Under the “Connectivity Tasks” section, choose Add a trusted certificate.

This will launch the Add a Trusted Certificate Wizard, which is where the CSR process begins.

Step 3: Start the CSR Generation

• In the wizard, select I want to buy a certificate from a certificate provider.
• Click Next.

This tells SBS that you want to generate a CSR file you can send to a Certificate Authority (CA).

Step 4: Fill in with Business details.

Here is where precision comes in. You’ll need to provide:

• Common Name (CN): It is typically your FQDN (e.g., remote.yourdomain.com).
• Organisation: Your legal business name.
• Organisational Unit (OU): Name of the department (e.g., IT, Web, Security).
• City/Locality: The city in which you have invested your business.
• State/Province: Please write the full name of your state.
• Country: ISO country code (two letters, e.g. US, IN, UK).

Step 5: Save the CSR File

• The wizard will create a CSR after inserting all the necessary information.
• Save the CSR file to a secure place (e.g. Desktop or C:\ drive).
• Open the CSR file with Notepad, and you will have something like this: ” —– BEGIN CERTIFICATE REQUEST —–“
• Your Certificate Authority (CA) will require you to give them this text.

Step 6: Submit CSR to Your CA

• After you have your CSR file, go to the site of the CA that you have selected.
• In the process of ordering the certificate, they will require your CSR. All you have to do is copy the whole text of the CSR with its BEGIN and END lines, and paste them into their form.

Once validated, you can be issued your SSL certificate by the CA, and install it on SBS.

Step 7: Installing the SSL Certificate on SBS 2008/2011

After receiving a certificate file from your CA:

• Return to the SBS Console Network connectivity.
• Once more, there is the option of clicking Add a trusted certificate.
• This time, I have a certificate that was given by my certificate provider.
• Visit the certificate file you have been provided with and fill in the wizard.

Your certificate is now in place and is prepared to accept your services. Creating a CSR on SBS 2008 / 2011 may be retro, yet they remain in use by several businesses. It is not complicated, just follow the steps and know where to click and what information to provide.

End Words

Your business information and credibility with customers are being threatened without a valid SSL certificate. The very first thing that you should do in order to make sure that your communication is safe, that your sensitive information is not transferred, or you do not see those horrible warnings of your browser, is to create a CSR.