Why Patch Management Remains the Most Annoying Problem in IT Security

Keeping your organisation’s systems secure can feel like an endless battle. Patch management and vulnerability mitigation are often seen as tedious tasks, but they form the backbone of effective cybersecurity. In this episode of the Security Strategist podcast, host Richard Stiennon and Mike Walters, co-founder of Action1, break down why patching remains challenging and share practical strategies to make the process simpler, smarter, and more effective. Patch Management Remains a Challenge #Patch management has been a concern since the earliest days of computing, dating back to mainframes and early PCs. Despite technological advances, it remains a "busy work" task that many IT teams find overwhelming. So what makes patching so hard today? One of the main reasons patching is still so difficult is the constant evolution of IT ecosystems. As Walters explains, "The biggest challenge is the ever-evolving nature of software with different applications, sources, and methodologies." Operating systems, third-party apps, and custom configurations all require tailored approaches for updates and patches, making uniform processes impossible. Large organisations often have hundreds or thousands of devices, each running different software versions requiring specific patches and testing before deployment. As Walters notes, "Remote endpoints become a big challenge. You need network-agnostic solutions that work regardless of whether a device is connected to the corporate network or a coffee shop." Innovative Solutions for Streamlining Patch Management To address these challenges, organisations are moving towards more intelligent and automated patching strategies. As Walters puts it, the starting point is simple: automation. By removing repetitive manual tasks, teams reduce the risk of human error and create space to focus on higher-value security work. Done properly, automation allows for scheduled updates, controlled testing, and the ability to roll back quickly if something goes wrong. At the same time, how patches are delivered matters just as much as when. Large updates can put significant strain on networks if pushed out all at once, which is why approaches like peer-to-peer distribution are gaining traction. By allowing endpoints to share updates locally, organisations can reduce bandwidth pressure and avoid bottlenecks. Modern environments are also driving a shift towards cloud-native, agent-based architectures. Instead of relying on a fixed network or VPN, these agents connect directly to cloud services, allowing patches to be deployed consistently across remote, mobile, and distributed devices. Finally, effective patching is as much about control as it is about speed. Progressive rollouts—testing updates on a small group before expanding—help organisations avoid widespread disruption. Action1’s Unique Approach Action1’s innovative model offers 200 free endpoints forever with no feature limitations, facilitating all sizes and types of organisations to implement effective patching solutions. By removing entry barriers, Action1 enables organisations to test, scale, and secure their patches more affordably. As Walters shares, "Offering free endpoints helps small IT teams get started, and as they grow, they stay with the platform."This approach promotes widespread adoption, accelerates security improvements, and creates a community of organisations committed to better vulnerability management. If you would like to find out more, visit: https://www.action1.com/ Takeaways - The history and persistent nature of patch management issues - How remote and hybrid work models impact patching strategies - The importance of network-agnostic, agent-based patching solutions - How to leverage automation and orchestration to reduce IT workload - Peer-to-peer distribution to optimise bandwidth during large-scale updates - Developing a phased, ring-based approach to #patch deployment - Action1’s unique offer of 200 free endpoints without feature limitations Chapters: 00:40 - Mike Walters’ background and company journey 02:00 - Why patching remains a complex, evolving task 04:35 - The need for specialisation and solving patching for good 05:11 - Why patch management feels like busy work and its inherent difficulties 06:44 - Lessons from early vulnerability management experiences 09:38 - Handling patching challenges for remote and mobile users 12:22 - Innovative bandwidth management using peer-to-peer distribution 14:55 - The value of automation and trust in large-scale environments 16:50 - Utilising update rings for safer, staged patch deployment 17:45 - Prioritising patching for zero-day vulnerabilities and rapid response 18:43 - Action1’s free tier for small IT environments supporting smaller organisations 24:53 - Closing thoughts: automation and proactive attack thinking #CyberSecurity #PatchManagement #VulnerabilityManagement