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Windows Patch Management Best Practices for MSPs and IT Admins

While patch management may not be the most exciting activity for sysadmins, it’s critical to ensuring the security of servers, applications, and operating systems. Managed service providers and sysadmins who fail to stay on top of patching expose their clients’ IT environment to security breaches and possible downtime of systems, services, and applications.

As such, enterprise patch management is a top priority for all organizations and should be treated as such. However, it’s no news that patches can break the systems they are meant to secure.

Generally, Windows sysadmins prefer to apply the latest patches alongside OS updates. These updates come with a whole lot of benefits: it helps secure the environment, prevents hackers from exploiting possible vulnerabilities, improves stability and performance, and fixes bugs in previous versions.

While these benefits are sought-after by system administrators, most updates come with several issues. New bugs and vulnerabilities are sometimes introduced which break essential services and other dependencies that ensure the smooth running of production environments.

To prevent such occurrences and safeguard the integrity of IT environments, let’s take a look at best practices for applying, scheduling, and managing patching activity for your clients.

Understand Patch Release Schedules and Plan Accordingly

Staying on top of patch release schedules helps you anticipate and effectively manage patch updates. Microsoft releases software patches on a monthly schedule — known as Patch Tuesday — and may sometimes release emergency patches when necessary. With this in mind, it’s a good idea to have a standard and emergency patching strategy in place.

Your standard patching strategy should detail the procedures for regularly scheduled updates and include timelines and maintenance windows. This gives sysadmins a timetable to work with (so they don’t fall behind on patch updates) and informs management and end-users when to expect occurrences that may affect production schedules.

On the other hand, emergency patching procedures detail the actions to be taken when patches are released outside standard schedules. This includes the steps for determining whether an emergency update is beneficial and notification procedures for end-users and affected departments. Emergency patches should only be applied when there is a clear security or business need.

PowerShell Remote Alerts

In this document you'll find a PowerShell script that checks the status of the services listed below and sends an email alert if any of them is turned off:

  • Windows Firewall
  • Windows Defender
  • Windows Update Service
  • Any installed third-party antivirus
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Use a Sandbox Environment to Test Patches

Sysadmins should never assume that applying a newly released patch will work without side effects. When applied, some patches break a process, feature, service, or interactions between system and services, leading to downtime. To prevent this, sysadmins should always test new patches in a patch testing environment, preferably a sandbox. The purpose of such an environment is to check the impact of the patch on an environment that closely mirrors the organization’s IT architecture to identify and control possible fallouts.

However, designing such a test environment isn’t fun. Fortunately, server virtualization has made it cheaper and easier for sysadmins to create and maintain such test environments. Any changes made to the organization’s production environment must be replicated in the test environment to ensure accurate testing.

Never Do First-Day Patching

While applying patches immediately they are released may seem like a good idea, such a patch management practice may do more harm than good. Some patches — especially those that come with Windows updates — contain errors that end up breaking something in production. This forces sysadmins to roll back to previous updates, impacting patch management timelines and causing downtime.

As such, you should allow adequate time to properly test new patches in a sandbox environment before rolling out to production. This rule should govern the preparation of patch management timelines.

Use Patch Management Tools

Getting patch management right requires a combination of speed, caution, adequate preparation, and judicious management. It also requires administrators to use the proper patch management tools, else patch updates can quickly fall behind.

Effective windows patch management begins from scanning and identifying missing patches to downloading and applying them. Doing this for all your organization’s endpoints (both off- and on-premise) can be a hassle and in the process, one or two systems may skip your attention and slip through the cracks. If this happens, your entire IT infrastructure is at risk.

You need a way to manage patching activities and provide the same level of coverage to all endpoints. With the right patch management solution, you can automate the Windows patch management process from start to finish and ensure that every endpoint on your network has been patched. This saves you the time and hassle of manually checking every computer to verify that all missing patches have been identified and patched.

Wrapping Up

Although Windows updates can introduce new issues, you should note that a lot of software vulnerabilities in your environment may come from non-Microsoft applications. This means you need comprehensive coverage of not only your operating system but also your applications. As such, effective management of OS and application patches is critical to the security of your IT environment.

Implementing the above best practices can help safeguard your production environments, secure vulnerabilities before they can be exploited by malicious hackers, and help you stay on top of Windows patch updates without breaking anything.

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This eBook provides an overview of how to design an efficient and effective network:

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