Top OS Patch Management Challenges to Address

For Hybrid Work Environments and Beyond

Written by Kelsey Kinzer on May 4, 2022

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Today’s workplace environments are no longer restricted to contained spaces with IT-controlled PCs as the center of productivity. Companies are increasingly becoming more distributed than ever before, with employees connecting to corporate resources through heterogeneous endpoints from different locations. 

While keeping the new hybrid workplace environment secure and up to date with the latest operating system (OS) patches is necessary, developing an effective patch management process has become increasingly challenging. In this article, we explore the top OS patch management challenges and how companies can address them.

Why OS Patch Management Is an Essential Cybersecurity Pillar

Patch management for OSs has remained a fundamental best security practice for decades. Many security breaches occur when hackers discover and exploit known vulnerabilities in operating systems, often unpatched assets. Unpatched OSs expose security risks and open the door to data corruption and loss, as well as availability and performance issues.

By conducting effective OS patch management, you can minimize such risks by closing down vulnerabilities and raising the entry barriers for hackers. While this approach largely worked in the past, today’s workplace environment has fundamentally changed. Every user wants to access corporate resources from any device, at any location, and anytime. 

Besides the skyrocketing endpoints, the number of applications that employees use for day-to-day operations has exponentially increased. According to Asana, an average employee uses at least 10 different applications for daily operations in the organization.

Hackers are also getting more sophisticated at discovering unpatched assets. Unlike in the past when no automated tools existed, today’s hackers can easily leverage automation to rapidly scan the web for any unpatched asset and penetrate the system. Because of these factors, operating system patch management has become truly indispensable. 

Top Challenges with OS Patch Management

Despite OS patch management being a crucial pillar of cybersecurity, many organizations still struggle with patching in hybrid work environments. This is due to many challenges, such as:

1. Heterogeneous versus homogeneous OS patch management challenges

It’s apparent that heterogeneous environments provide more benefits to organizations through improved user experience and productivity than homogenous workplaces. However, heterogeneous environments are far more complex to manage. In a typical heterogeneous workplace environment, you’re likely to have desktops running Windows, macOS, and different iterations of Linux. 

You’re also likely to have some employees bringing in their notebooks and tablets that run Windows, macOS, Linux, iOS, and even Chrome OS, complicating things further with the bring-your-own-device (BYOD) phenomenon. Under such environments, it isn’t easy to keep track of OS version updates on multiple devices. The process is even more complex for small to mid-sized enterprises (SMEs) that operate under tight budgets with limited manpower.

2. Ensuring patch management software is secure is a challenge

The growth of cloud-based services has been exponential over the last couple of years because cloud computing provides numerous benefits such as mobility, enhanced agility, and cost savings, among others. Unlike legacy OS patching which is simpler to manage, the shift to cloud-based services presents unique challenges in software patching. 

With the geographically distributed endpoints to keep track of, IT teams must employ new approaches to protect corporate resources from attacks. One unpatched server or device can expose the entire enterprise network to attacks from threat actors. Besides the endpoints, cloud-based applications have the potential for more vulnerabilities when you don’t adhere to the shared responsibility model

Under the shared responsibility framework, the cloud service provider (CSP) can only manage the security of the cloud itself while you handle the security of data. However, holding up the organization’s end of the shared responsibility bargain can be difficult, especially if you don’t have enough specialized IT staff. 

3. Addressing remote and dispersed workforces is an issue

IT teams can easily leverage legacy OS patch management tools that require on-prem access to devices in a traditional office setting. However, this isn’t possible with a remote and dispersed workforce where employees reside in diverse locations with different time zones. This is because it’s impossible and not convenient to have IT teams on-site to patch systems or check on processes. 

While legacy OS patch management solutions work well in an on-prem setup, they don’t provide remote control, distribution, and patch checking capabilities. This modern setup requires a cloud-native patch management strategy. 

4. Patching is time-consuming

The faster IT teams apply the appropriate patch to the OS, the more foolproof your environment becomes. However, hundreds of software updates and patches get released daily. Applying every update or patch immediately after the vendor releases it can overwhelm IT teams and even enterprise networks. 

A typical company can spend as much as 18,000 hours on patching activities. There’s also an added concern about downtime and lost business if the update or patch requires a system reboot. An automated OS patch management tool can help you group the patches into categories, prioritizing the most important ones and minimizing those with the most negligible potential impacts.

5. Patch testing can be complex

The primary objective of patching is to fix bugs, eliminate vulnerabilities, and add new features to the operating system. However, without prior testing, patching an operating system can make the software unstable or introduce unknown risks. IT teams need to test the patch in a non-production environment to ensure a predictable rollout. 

Since software vendors constantly release patches, testing should be an ongoing process in organizations. However, like OS patching, testing can also be time-consuming, requiring many hours to complete. An automated patch testing solution can help you fast-track the deployment of OS patches while mitigating many risks associated with running untested and unpatched applications. 

6. Maintaining compliance can be a challenge

Financial institutions and healthcare providers are some sectors with the strictest regulatory compliance requirements. Because unpatched OSs can result in serious cybersecurity breaches, many industry associations and regulators have mandated OS patch management compliance.

Organizations operating in these sectors must document proof of continuous compliance and pass periodic reviews. Unfortunately, many companies don’t have the requisite tools to assess their patching needs and provide clear visibility into the entire OS patch management lifecycle.

An automated cloud-based tool such as the JumpCloud Directory Platform® can help you address this problem because you can easily see patch states across your network—whether on-site, cloud, or remote. This allows you to deliver a complete picture of the entire OS patch status anytime, from anywhere.

JumpCloud Directory Is a Simple and Cost-Effective OS Patch Management Solution

Understaffed and alert-fatigued companies require more effective ways to eliminate exposure to vulnerabilities in the wake of increased cybersecurity attacks and a rapidly growing attack surface. JumpCloud is an out-of-the-box cloud directory platform that IT teams can use to secure corporate resources in heterogeneous work environments.

As a cloud-native solution, JumpCloud can enforce OS patch management, security policies and configurations, and customized scripting across Windows, macOS, and Linux from a single console no matter where devices reside. IT teams can quickly gain control and share visibility in on-prem and remote endpoints without the need to deploy costly patch management solutions.

By leveraging JumpCloud’s robust System Insights and patch management policies, IT teams can easily prioritize mission-critical assets in their journey to secure corporate resources, all from one consolidated console. Learn more about how JumpCloud can help you eliminate vulnerabilities with simplified patch management. Try out the full functionality of the platform with JumpCloud Free — get up to 10 users and 10 devices free with 24×7 in-app support for the first 10 days. Utilize System Insights and JumpCloud patch management functionality to reduce the chance of human error, regain your valuable time, improve your organization’s security posture, and leverage the latest features and technologies available.

Kelsey Kinzer

Kelsey is a passionate storyteller and Content Writer at JumpCloud. She is particularly inspired by the people who drive innovation in B2B tech. When away from her screen, you can find her climbing mountains and (unsuccessfully) trying to quit cold brew coffee.

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