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Testing Kerberos Constrained Delegation in a Hyper-V Lab

#1
09-26-2024, 11:17 PM
Testing Kerberos Constrained Delegation in a Hyper-V Lab

Configuring Kerberos Constrained Delegation (KCD) in a Hyper-V environment can at first feel a bit daunting, but it's totally manageable once you grasp the key components and processes. It’s particularly crucial for scenarios where services need to interact with one another securely without compromising the security credentials of the user. KCD is essential in environments where you may have services that request other service tickets to access resources on behalf of a user, something that often comes into play in larger or more complex setups.

Let’s say you’ve set up your Hyper-V lab and you want to test KCD with a SQL Server instance or another service that is needed to interact with your Hyper-V host. First, the setup requires an Active Directory (AD) domain. You need to ensure that your client machines, servers, and services are all part of this AD domain. Assuming you have a Windows Server machine where Hyper-V is installed, all your resources should be properly set with DNS settings pointing to this AD domain.

You need to install Hyper-V on your Windows Server. Once that is done, create a few virtual machines. One of these can be a Domain Controller, which serves as the authentication point for KCD. Another virtual machine can be a file server, for instance, which will need access to the SQL service.

After you have your environment set up, the next step is to configure service accounts in Active Directory. When dealing with SQL Server or similar services, you will likely want to create a Managed Service Account or a Group Managed Service Account, depending on your needs. These accounts can automatically handle password management for you, which generally simplifies your administration tasks. The service account must be given the permission to delegate access. You can set this via the properties of the service account in AD. Just navigate to the Delegation tab and choose “Trust this user for delegation to specified services only.” Then, specify the service that you’ll delegate, which is usually just the SQL Server instance running on one of your Hyper-V guests.

At this point, you have launched into configuring your SQL Server to enable it to be trusted for delegation. When you look at the SQL Server properties, you’ll want to ensure that the authentication mode is set to allow Windows Authentication. You then must set appropriate SPNs (Service Principal Names) for your SQL Server instance. The SPNs should look like this:

setspn -A MSSQLSvc/hostname:port domain\SQLServiceAccount

When substituting 'hostname' with the name of your SQL server and replacing 'port' with the correct SQL Server port (default is 1433), it allows Kerberos authentication from clients to that SQL service. If you use the 'setspn -L SQLServiceAccount' command, you can check that the SPNs have been registered correctly.

After the SPNs are set, your next step is to make sure that your SQL Server has the appropriate permissions to perform actions on behalf of the user account that's trying to access it. That’s when the real testing comes in.

Now switch to one of your client machines in the lab. When you are logged in as a user who is authorized to access files and database records on SQL, you can run a PowerShell script to check whether the delegation is working. If you utilize the 'klist' command, it’s possible to view the Kerberos tickets that have been issued to you. It will list the credentials that are being used, and you should see ticket grants for both the user account and the SQL Server account.

To generate Kerberos tickets, you can execute:

klist

If everything is working as planned, you should see the appropriate tickets listed. If you don't see the expected tickets or encounter any issues regarding Kerberos authentication between your VMs, this typically indicates a misconfiguration in the KCD setup.

In a working environment, testing could involve simulating an application that connects to your SQL Server. Let’s assume you create a PowerShell application that calls the SQL Server database from a client machine to verify successful connection and delegation. Using an application framework like .NET with the appropriate SQL connection string, you can check for data retrieval or any other transactions necessary for the application’s operation within your lab.

For instance, if you have a connection string that looks like this:

$connectionString = "Server=SQLServerName;Database=YourDatabase;Integrated Security=True;"

Executing any SQL command from the application should return results if KCD is functioning correctly. You could even use SQL Server Management Studio to log in as the user and run queries directly, which will also allow you to check whether your KCD configuration is firing on all cylinders.

Don't forget that the Windows Firewall can become a hurdle if not configured properly. Make sure the necessary ports for SQL Server and other relevant services are open. Sometimes, placements within your network can also impinge on the outcomes; you may want to try testing from multiple VMs to simulate how things would work in a larger deployment.

If you run into issues, searching through the event logs on both the client machine and the server can provide some hints about misconfigurations. Look specifically for Kerberos errors that explain the authentication failures. The event logs usually give you error codes which can be cross-referenced with Microsoft documentation.

During your testing, it can be beneficial to utilize tools like Kerberos Configuration Manager for SQL Server. This is a Microsoft tool destined to help analyze service configuration settings, helping to easily identify potential issues in the setup that you may not be aware of. It can streamline the troubleshooting process significantly and ensure that every little configuration detail is checked.

As you’re working through KCD, keep an eye on group policy settings as well. These policies can impact user service delegations and might restrict KCD behaviors. Modifying group policies might become necessary if defaults are set in such a way that they conflict with your KCD objectives.

If everything is functioning as expected, you’ll reach the point where your delegated access is secure without compromising the integrity of user credentials. This smooth exchange of authentication is a significant benefit of KCD when running your applications remotely.

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When you wrap up your testing, documenting each step you completed helps not just understanding the KCD better, but also aids in future troubleshooting or even reproducing the environment as needed. Recommendations usually include screenshots of configurations, PowerShell commands run, and the outcome of the tests. This way, if you encounter a similar situation down the road, you won't have to start from scratch.

Monitoring your implemented strategy with performance counters can also help you see how KCD performs with actual user loads. You should run several tests under load, particularly if your applications will be heavily used in production.

With proper testing, hyper-perfomance issues should be picked up immediately, allowing you to optimize where needed. It’s even worthwhile to include some load testing or concurrent access testing as part of your evaluation process, to gauge how the setup behaves under greater stress.

After all is said and done, KCD can serve a critical role in enhancing security without negatively impacting user experience. Once you’ve verified everything works as expected with the appropriate delegation of credentials, you can confidently configure more complex integrations or applications as the environment grows.

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Philip@BackupChain
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Testing Kerberos Constrained Delegation in a Hyper-V Lab - by Philip@BackupChain - 09-26-2024, 11:17 PM

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