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Why Neglecting OS Patches Puts Your Entire Network at Risk
Config hardening
Misconfigs
Threat Actors
Attacks are becoming more sophisticated, hackers are becoming smarter, and so should be the defenders. The attacker eyeing your organization is looking for the misconfiguration that will let them in. So should you.
We're always on the lookout for these misconfigurations, as they could be exploited by threat actors resulting in a cyberattack such as ransomware.
Common causes of misconfiguration are human error. This is where the IT practitioner either lacks the correct skills for the tasks at hand, or they falsely believe that the task has been completed correctly.
At Remedio, we frequently witness and report software-update management mistakes. In this post we will cover some of the common ones, and how to find them.
Up to Snuff on Being Up-to-Date?
Keeping your OS and other applications up-to-date with the latest patches is important to ensure you have all the critical updates to keep your environment secure.
Patch Tuesday is the name given to when Microsoft releases its Cumulative Updates (CU) which is typically the second Tuesday for each month (and sometimes the fourth Tuesday).
Most organizations will use the Microsoft SCCM tool to manage software updates. There are many great guides or online videos which can walk you through the steps to achieve this using the tool. The general process is:
- Sync software updates
- Create Software update group
- Create Software update package
- Deploy
If you are familiar with the process you will know there are many steps and configurations required to perform what appears a simple task.
However, there are two types of misconfigurations which can cause a security risk and act as an initial attack vector by hackers:
- Not choosing all the required patch update packages
When using SCCM, you need to select all the relevant and required patch updates when creating the software update package.
The long list of updates available covering all Microsoft products often results in confusion and not all the updates selected.
We often speak with customers who believe they have correctly selected the right updates and their endpoints are up to date. Yet, when the endpoints are analyzed by Remedio Validator, we will find this not to be the case.
- Workstations and Servers are not updating
Once the SCCM has successfully deployed the update package, the endpoints and servers will be triggered to perform the update. Not all endpoints & servers will receive the trigger message or are able to successfully perform the update.
While there are retry mechanisms, some will end up not updated and this can continue from month to month. This scenario is becoming much more common in recent times especially with employees working from home and not using a VPN to connect to their organization’s network, which is required to receive the update.
An Elegant Solution
To keep an organization secure, the IT and SecOp teams need to ensure all endpoints are patched and up to date. They need the visibility on the status of patch updates on all endpoints including those who are remote and not connected via a VPN.
Remedio is helping organizations overcome these two common misconfiguration scenarios.
Firstly, it monitors all workstations and servers in an organization and will identify & alert to IT Admins and SecOps when the baseline is out of date/ missing critical patches. Secondly, it will also report which endpoints have not been updated and allowing remediation actions to be taken.
Remedio is constantly reporting the endpoint status, whether it’s connected to the network or working from home remotely.
FAQ
Why are missing operating system patches still one of the leading causes of cyberattacks?
Missing operating system patches leave known vulnerabilities exposed long after fixes are available. Attackers routinely scan for systems that have not received security updates because exploiting a known weakness is faster and more reliable than developing a new exploit. Even a single unpatched endpoint can provide an initial foothold for ransomware, credential theft, or lateral movement.
Why do organizations miss patches even when they use Microsoft SCCM or other patch management tools?
Patch management tools automate deployment, but they cannot guarantee successful installation. Common issues include incomplete update packages, offline or remote devices, VPN dependency, deployment failures, conflicting policies, and endpoints that never report successful installation. Organizations need continuous verification that patches were actually applied, not just deployed.
How can organizations verify that every endpoint is fully patched?
The most effective approach is to continuously validate the patch state of every endpoint against the organization's security baseline. This should include laptops, servers, remote devices, and systems that are not always connected to the corporate network. Verification should confirm successful installation rather than relying solely on deployment status.
What risks do remote and hybrid workforces create for operating system patching?
Remote endpoints frequently miss scheduled updates because they spend long periods disconnected from the corporate network or VPN. Over time, these devices accumulate missing security updates and become attractive targets for attackers. Continuous monitoring and remediation help ensure devices remain compliant regardless of their location.
Is deploying a patch the same as successfully remediating a vulnerability?
No. Deploying a patch simply starts the update process. Successful remediation requires confirming that the update installed correctly, the vulnerability has been eliminated, and the endpoint remains compliant over time. Without validation, organizations can develop a false sense of security.
How often should organizations audit their operating system patch status?
Patch status should be monitored continuously rather than reviewed during periodic audits. New vulnerabilities emerge every month, devices regularly drift from their intended configuration, and failed updates can occur at any time. Continuous assessment reduces the window of exposure between a failed update and its detection.
What is the difference between patch management and vulnerability management?
Patch management focuses on deploying software updates, while vulnerability management identifies, prioritizes, and tracks security weaknesses across the environment. Effective security requires both disciplines working together, with continuous validation confirming that patches have successfully reduced exposure.
Can unpatched operating systems affect regulatory compliance?
Yes. Frameworks such as CIS Controls, PCI DSS, NIST CSF, ISO 27001, and Cyber Essentials all require organizations to maintain secure and up-to-date systems. Failure to apply critical security patches can result in compliance gaps, increased audit findings, and elevated business risk.
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