Service Outages & Cybersecurity Failures — Lessons from Cloudflare | Security Boulevard Ep. 10

In Ep. 10 of the Security Boulevard Podcast, Tom Hollingsworth, Fernando Montenegro, and Mitch Ashley take a closer look at how service outages reveal deeper cybersecurity challenges. Using recent Cloudflare incidents as a reference point, the conversation highlights how dependent organizations have become on complex, interconnected infrastructure.

The panel discusses the importance of building resilience into systems, the economic pressures that influence cybersecurity decisions, and the need for strong threat modeling and preparation for unexpected failures. They also reflect on what past outages teach us about maintaining operational integrity when critical services go down.

As cybersecurity and reliability concerns continue to overlap, the lessons from these outages provide a roadmap for strengthening modern systems against both technical failure and active threats.

Hosts

• Tom Hollingsworth

• Fernando Montenegro

• Mitch Ashley

Listen to the full episode and see future installments at SecurityBoulevard.com