MSP 1337 | Cybersecurity Education & Security Guidance

Join Alane Boyd, founder of Biggest Goal and an AI/security educator, as she dives into the complex landscape of AI. Discover the risks of free AI tools and the importance of robust AI policies for organizations. Alane clarifies how AI agents serve as autonomous digital workers and explores practical applications, from automating ticket management to enhancing vendor validation. She also emphasizes the need for mental health balance in our tech-driven lives. Tune in for insightful tips on making AI work safely for your team!

Chris Johnson and cybersecurity expert Robert Siciliano dive into the human side of security, exploring why default trust and denial make people vulnerable to social engineering and cyber threats. They discuss the cultural framing of security, the importance of personalizing security practices, and why leadership must model proactive behaviors. The conversation introduces the concept of a “strategic human firewall,” emphasizing that proper protection comes from security appreciation, not just awareness. From AI-driven fraud and voice cloning to practical steps like password managers and two-factor authentication, this episode highlights how mindset shifts and personal responsibility are key to resilience in today’s threat landscape.

Resilience and Continuous Improvement for ITSPs as we go into 2026. I discuss what it means to be on a resilience journey with Charles Love of ShowTech Solutions. ShowTech Solutions has reached a milestone in its maturity journey, achieving Assured status, and continues to advance its maturity process. Experiences and lessons learned that will help any ITSP on their own journey.

Predictions and challenges in the technology and cybersecurity space for 2026, with a focus on Microsoft ecosystem changes, licensing, security, and the impact of AI and Copilot. I had a chance to catch up with Shay Cohen of Optimize365.io this week, and I think you will find his insights on the future of CoPilot and other unique changes we can expect in 2026.

In 2026, AI will increasingly integrate into business processes, emphasizing strong data quality and security as prerequisites for success. AI agents, distinct from chatbots, will operate with machine identities to automate tasks while supporting, rather than replacing, human decision-making. This is just a glimpse of the insights Ben Wilcox of ProArch shared this week.

Looking ahead to 2026 trends and challenges in the MSP (Managed Service Provider) space, focusing on AI, automation, security, risk management, and social engineering. In a conversation with Josh Hohbein of Centrex IT, we discussed the key challenges and opportunities as we enter 2026.

Predictions for the Managed Service Provider (MSP) cybersecurity landscape in 2026, with a focus on risk management, the continued importance of basic cyber hygiene, open-source adoption, and the strategic use of risk registers. Did I say Risk Register? Dom Kirby brings it home: the importance of the Risk Register and its role as we enter 2026. He advocates that MSPs move beyond discussions of technical tools and engage in business and risk conversations with their clients.

In this engaging discussion, Chris Loehr, a cybersecurity practitioner and industry commentator, delves into the complexities of cybersecurity budgeting for 2026. He highlights how private equity influences financial decisions, leading to unpredictable changes in spending. Chris also emphasizes the importance of staged security improvements and aligning security measures with business goals. As clients grow more risk-averse, he encourages MSPs to adopt consultative approaches and ensure realistic security expectations, framing cybersecurity as essential for productivity and protection.

From what keeps us up at night, to just meeting the minimums and nothing more to be compliant. Dorota Ulkowska of Accurate Networks and I discuss the recurring challenge of clients, tiny businesses, resisting recommended cybersecurity practices due to cost, perceived inconvenience, or a belief that risks are exaggerated, with Dorota providing real-world examples from their experience at Accurate Networks.

Sitting down with Bobby Glen James of Boteka about the importance of simplicity in IT security for MSPs. Bobby shares lessons from decades in the industry, advocating for Lean IT practices, streamlined technology stacks, and a service-first approach that avoids hardware upselling and long-term contracts. Practical insights on risk management, prioritizing critical systems, and building resilient, client-focused MSP services.