Windows Patch Management Best Practices for MSP and IT Pro

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

Windows Patch Management Best Practices for MSP and IT Pro

For this reason, 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.

To prevent such occurrences and safeguard the integrity of IT environments, let’s take a look at best practices for:

  • applying patches
  • scheduling patches
  • managing patching activity.

Content Summary

Define Roles and Responsibilities
Regularly Update the Software and Hardware Inventory
Categorize Assets
Understand Patch Release Schedules and Plan Accordingly
Classify Patches
Use a Sandbox Environment to Test Patches
Never Do First-Day Patching
Use Patch Management Tools
Wrapping Up

Generally, Windows sysadmins prefer to apply the latest patches alongside OS updates. Applying updates comes 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, 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.

Patch Management Best Practices

Simply having patch management in place is never enough. The stability and great performance of your systems depend on these best practices and additional steps you can take to streamline your patch management processes.

Define Roles and Responsibilities

First, you should clearly understand who’s in charge of reviews, approvals, and releases. Due to the evever-growingomplexity of IT environments, it becomes incredibly difficult to track patch deployments if you don’t know who’s responsible for each action.

To simplify these routines, MSPs and IT professionals can create distinct groups with operational responsibility for various stages of the patch management process, like patch analysis and research, prioritization, verification and approval, and testing and deployment. Be sure, as well, to define the notification and reporting processes for each group or team member.

Regularly Update the Software and Hardware Inventory

If you don’t have an accurate list of assets, you can’t be sure that all of them are kept up-to-date. Keep records of all the assets you have, including:

  • Software and hardware types
  • Names and versions
  • Activity status
  • EOL dates
  • License expiration dates
  • Warranties, and other important information associated with each asset

Categorize Assets

Once you’ve finished with the asset inventory, start categorizing your software and hardware by severity level, based on the threat they pose to the business. Performing periodic audits and continuous scans of your IT assets helps you assess which security vulnerabilities or other problems may impact the environment due to insufficient updates.

This also helps to determine which assets should be patched first, and which can be prioritized lower.

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 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 clear security or business need.

Classify Patches

To ensure the smoothest process for installing patches, use this classification to define the importance of patches:

  • Critical patches: Security updates, vital performance-related patches. Should be installed immediately or within hours.
  • Regular patches: Related to non-critical fixes and routine updates. Can be installed when most systems are not active, which could take up to a week or more.
  • Missed or failed patches: Record patches that were not installed for some reason. Investigate the issue and restart this process if needed.
  • Blacklisted patches: Research multiple sources about each patch you’d like to install; some of them can be harmful. It’s crucial to prove that the reason that this patch wasn’t deployed was that it was irrelevant, not because it was missed.

Use a Sandbox Environment to Test Patches

You 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, you 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 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 after 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 you to roll back to previous updates, impacting patch management timelines and causing downtime.

Consequently, you should allow adequate time to properly test new patches in a sandbox environment before rolling them 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, otherwise, patch updates can quickly fall behind. Patch management functionality is often included within the feature set of RMM tools, which makes the whole process of monitoring and management easier.

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.

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 that you need comprehensive coverage of not only your operating system but also your applications. So 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.