Cybersecurity News & Analysis by Cyber Sidekicks - Your Weekly Update’

Jon Abbott, CEO of ThreatAware joins Christina and Rory this week to chat about all things software-related! Jon argues that while AI rapidly accelerates initial software creation, the true enterprise challenge lies in delivering long-term maintenance, SLA guarantees, and dependable support across subsequent release cycles. He cautions that despite media narratives surrounding "sophisticated" AI cyberattacks, most security incidents stem from fundamental hygiene failures—such as unpatched vulnerabilities, missing multi-factor authentication (MFA), or default passwords on internet-exposed devices. While optimistic about the future of technology, Jon urges security leaders to stop lowering security barriers for user convenience or agentic AI tools, calling for a stricter, mature security posture rooted in continuous monitoring and "defense-in-depth".
NEWS
CrowdStrike Reportedly Paying $495 Million for AI Security Firms Fiddler and Dreadnode
Akamai releases its State of the Internet (SOTI) - The Fraud and Abuse report 2026
 
 
We welcome your feedback and suggestions, so please send us a message! Christina Richmond – christina@richmondadvisorygroup.com Rory Duncan – rory@richmondadvisorygroup.com Subscribe to our Newsletter - "Signal, not noise"Our monthly newsletter is free to subscribers! Sign-up now at Richmond Advisory Group.   Technology we use Podcast Recording Platform(s) – Cleanfeed & Riverside Cyber Sidekicks Show Host – Podbean Edited & mastered in GarageBand & Final Cut Pro

This week, hosts Christina Richmond & Rory Duncan are joined by Jon-Rav Shende, CISO of AI & Data at Thales! Christina has known John for over a decade, and his expertise in cybersecurity, particularly in AI applications, provides invaluable insights into the evolving landscape of the industry.
NEWS
Anthropic files for its IPO, revealing an $80B loss in 2026
Anthropic's recent IPO filing and its implications for the industry. Anthropic has recently filed its S1, marking a significant step towards its IPO. This document reveals not just their revenue figures but also their challenges and strategies in the AI landscape. While they reported over $16 billion in revenue for the first half of 2026, it’s important to note their $80 billion loss forecasted for the same year. Rory highlights how Anthropic's investments in AI infrastructure surged to $9 billion in just the first half of the year, indicating a strong commitment to growth despite the financial hurdles.
"AI cybersecurity is simultaneously a critical vulnerability, an operational hurdle, and a strategic commercial opportunity." — Rory Duncan
Christina shares insights on how AI technologies function as a double-edged sword in cybersecurity. They can be utilized by malicious actors to generate malware and exploit software vulnerabilities, while also empowering defenders to enhance their security measures.
"Advanced models function both as this dual-use tool capable of generating malware...and helping defenders with cyber operations." — Christina Richmond
The discussion emphasizes the urgent need for organizations to leverage AI responsibly, balancing its potential for good against its misuse by adversaries.
Cybersecurity Issue Forces a Major New Mexico Hospital to Divert Patients and Close Clinics
A significant topic of concern was a recent attack on the University of New Mexico health system. Rory and Christina note that such attacks are not just disruptive but pose life-threatening risks, especially in critical infrastructure like healthcare. They stressed the importance of securing these systems to prevent devastating consequences for patient care.
As we navigate these complex challenges in cybersecurity, it’s essential to stay informed and proactive. For a deeper understanding, listen to the full episode of Cyber Sidekicks, where we unpack these issues and more.
We welcome your feedback and suggestions, so please send us a message! Christina Richmond – christina@richmondadvisorygroup.com Rory Duncan – rory@richmondadvisorygroup.com Subscribe to our Newsletter - "Signal, not noise"Our monthly newsletter is free to subscribers! Sign-up now at Richmond Advisory Group.   Technology we use Podcast Recording Platform(s) – Cleanfeed & Riverside Cyber Sidekicks Show Host – Podbean Edited & mastered in GarageBand & Final Cut Pro

In this week's episode, Christina and Rory chat with returning guest Randy Barr, CISO at Cequence Security about the need for CISOs to retain deep technical credibility while operating at the board level. Pointing to the risk of unmonitored shadow AI, rogue internal agents acting unexpectedly, and the urgent need for strict containment guardrails, Randy outlines his his primary operational concerns. He also gives insights into how his team builds in-house AI agents to bridge IT and security operations by pulling federated telemetry across disparate tools and automating vulnerability triage.
FYI - Alongside his philanthropic educational work modernizing cybersecurity curricula in the Philippines, Randy is now contributing to the Cloud Security Alliance’s Catastrophic Risk Annex.
NEWS
IBM launches X-Force Advanced Proactive Security to put frontier AI to work in enterprise security testing
US Agencies Detail Incident Response Practices for Rogue AI Agents
Cybercrims go beyond stealing data to attack physical building systems
Rory is somewhat overawed by the HP's new OmniBook Ultra 16 laptop with its Nvidia RTX Spark SoC + 128GB RAM...! 
 
We welcome your feedback and suggestions, so please send us a message! Christina Richmond – christina@richmondadvisorygroup.com Rory Duncan – rory@richmondadvisorygroup.com Subscribe to our Newsletter - "Signal, not noise"Our monthly newsletter is free to subscribers! Sign-up now at Richmond Advisory Group.   Technology we use Podcast Recording Platform(s) – Cleanfeed & Riverside Cyber Sidekicks Show Host – Podbean Edited & mastered in GarageBand & Final Cut Pro

While Rory is at the Cisco EMEA Analyst Event, Christina chats with Dov Yoran, Co-Founder / CEO of Command Zero, discussing the topics of modernizing SOC investigations, maintaining deterministic rigor in an AI-driven world, and empowering the human security analysts. 
Rather than replacing SOC analysts or stockpiling raw logs, Dov argues that using curated, deterministic logic to query disparate data silos in real time helps deliver transparent, repeatable investigations. He believes that this approach up-skills Tier 1 analysts and enables pragmatic, guided remediation that automatically builds compounding organizational knowledge over time.
NEWS
Rory gives us a re-cap of his two-day visit to Cisco's EMEA Analyst summit, sharing his thoughts on the vendor's product and go-to-market strategy, how geopolitical considerations affect customers in EMEA, and the importance to Cisco of trust.....
Adobe software dupe maker takes on Microsoft Office, releasing free versions of Word, Powerpoint, and Excel
 
 
We welcome your feedback and suggestions, so please send us a message! Christina Richmond – christina@richmondadvisorygroup.com Rory Duncan – rory@richmondadvisorygroup.com Subscribe to our Newsletter - "Signal, not noise"Our monthly newsletter is free to subscribers! Sign-up now at Richmond Advisory Group.   Technology we use Podcast Recording Platform(s) – Cleanfeed & Riverside Cyber Sidekicks Show Host – Podbean Edited & mastered in GarageBand & Final Cut Pro

Hosts Christina Richmond and Rory Duncan are joined this week by Glenn Weinstein, CEO of Cloudsmith to discuss building high-performing company cultures, navigating software supply chain risks, and securing modern development workflows. To counter machine-speed AI threats, Glenn proposes that organizations must embed automated "don't make me think" security guardrails directly into workflows so developers don't expend cognitive energy on manual vulnerability checks. Much like sports team management taking care of logistics so athletes can focus on competing, leadership should automate background security tasks to free developers to concentrate on solving core customer problems.
NEWS
US Senate Passes Bipartisan Bill to Strengthen Healthcare Cybersecurity
Temporal buys AI security startup Oso weeks after raising $550M
RSA Launches RSA Agent ID, an agentic identity security platform for highly regulated industries
 
We welcome your feedback and suggestions, so please send us a message! Christina Richmond – christina@richmondadvisorygroup.com Rory Duncan – rory@richmondadvisorygroup.com Subscribe to our Newsletter - "Signal, not noise"Our monthly newsletter is free to subscribers! Sign-up now at Richmond Advisory Group.   Technology we use Podcast Recording Platform(s) – Cleanfeed & Riverside Cyber Sidekicks Show Host – Podbean Edited & mastered in GarageBand & Final Cut Pro

This week, Andy Hornegold, Chief Security Technologist and Head of Product at Intruder joins hosts Christina Richmond and Rory Duncan to discuss offensive security, the economics of defensive AI, and how organizations can stay ahead of modern threat actors.
The trio conclude that, to navigate rapid threat evolution and the rising costs and guardrails of commercial frontier models, defenders must prioritize fundamental attack surface reduction and lean toward specialized or open-source models for cleaner vulnerability triage.
NEWS
Akamai publishes its latest State of The Internet (SOTI) report, titled “Speed, Scale and Non-Human Identity: The Agentic Threat Landscape”
CISCO Talos Discovers Closed Quorum: the first reported autonomous AI C2 implant
We welcome your feedback and suggestions, so please send us a message! Christina Richmond – christina@richmondadvisorygroup.com Rory Duncan – rory@richmondadvisorygroup.com Subscribe to our Newsletter - "Signal, not noise"Our monthly newsletter is free to subscribers! Sign-up now at Richmond Advisory Group.   Technology we use Podcast Recording Platform(s) – Cleanfeed & Riverside Cyber Sidekicks Show Host – Podbean Edited & mastered in GarageBand & Final Cut Pro

Chris Newton-Smith, CEO of ISMS Online returns as a guest on this week's episode, discussing with Christina and Rory about how organizations can bridge the gap between perceived readiness and actual operational resilience given the challenges of both fair and foul uses of AI and AI Agents. Chris argues that to bridge the gap between perceived AI readiness and actual operational capability, organizations should adopt an integrated "resilience loop" that expands existing information security and data privacy frameworks. The hosts and Chris conclude that because complex digital systems make unexpected failures statistically inevitable, security leaders must use disciplined risk registers to prioritize resources and actively test incident response before a breach occurs.
NEWS
IBM Acquires Logiq Consulting
Fime acquires French cybersecurity specialist Red Alert Labs
Japan Dismantles First North Korean Laptop Farm as US and Allies Detail Wider Scheme
 
We welcome your feedback and suggestions, so please send us a message! Christina Richmond – christina@richmondadvisorygroup.com Rory Duncan – rory@richmondadvisorygroup.com Subscribe to our Newsletter - "Signal, not noise"Our monthly newsletter is free to subscribers! Sign-up now at Richmond Advisory Group.   Technology we use Podcast Recording Platform(s) – Cleanfeed & Riverside Cyber Sidekicks Show Host – Podbean Edited & mastered in GarageBand & Final Cut Pro

In this week's episode, Christina & Rory talk with Tom Kellermann, VP of AI Security & Threat Intelligence at TrendAI about how rogue nation-states and AI-driven offensive tactics are disrupting traditional cybersecurity defenses. Tom outlines how four rogue nation-states—Russia, China, North Korea, and Iran—are collaborating and sharing command-and-control (C2) capabilities and exploits at unprecedented levels. He explains how Russian guidance is elevating second-tier actors, driving destructive attacks against critical infrastructure like energy and water utilities, while these states actively shield cybercrime cartels as national assets.
NEWS
Anthropic promises zero data retention – but customers must check it worked
Nvidia’s Huang says cybersecurity will be next major AI use case
EU Cyber Resilience Act (CRA): Reporting obligations now in effect
NEXT WEEK'S GUEST
Next week's guest is Chris Newton-Smith, CEO of ISMS Online.
 
We welcome your feedback and suggestions, so please send us a message! Christina Richmond – christina@richmondadvisorygroup.com Rory Duncan – rory@richmondadvisorygroup.com Subscribe to our Newsletter - "Signal, not noise"Our monthly newsletter is free to subscribers! Sign-up now at Richmond Advisory Group.   Technology we use Podcast Recording Platform(s) – Cleanfeed & Riverside Cyber Sidekicks Show Host – Podbean Edited & mastered in GarageBand & Final Cut Pro

This week, host Rory Duncan speaks with guest Raghu Nandakumara, VP of Industry Strategy at Illumio, discussing why traditional security controls are failing against modern threats and why enterprises must prioritize containment and business-led resilience. Raghu emphasizes that while foundational security hygiene is frequently neglected for attractive new technologies, containment must serve as the essential "third pillar" alongside prevention and detection to disrupt the fundamental physics of cyber attacks. His recommendation: to prevent systemic operational shutdowns, organizations must abandon blanket policies across all assets and instead prioritize protecting their most critical business processes to effectively reduce overall operational risk.
NEWS
Criminals publish data of 8.7m people after UK airports hack
153 million Driver License images exposed via IDScan.net leak
 
 
We welcome your feedback and suggestions, so please send us a message! Christina Richmond – christina@richmondadvisorygroup.com Rory Duncan – rory@richmondadvisorygroup.com Subscribe to our Newsletter - "Signal, not noise"Our monthly newsletter is free to subscribers! Sign-up now at Richmond Advisory Group.   Technology we use Podcast Recording Platform(s) – Cleanfeed & Riverside Cyber Sidekicks Show Host – Podbean Edited & mastered in GarageBand & Final Cut Pro

This week, Christina & Rory are joined by Fractional CISO, Risk & Governance expert,  - and soon to be author - Kayne McGladrey as he returns to the show to discuss the complex and rapidly evolving legal and financial realities of AI liability. Who takes the fall when AI systems make critical errors, violate copyrights, or leak data? The discussion delves into the pros and cons of open-weight models i.e. they save money on token costs, but the deploying company must assume 100% of the liability for both inputs and outputs, unlike when using a frontier model (like Microsoft or OpenAI), the company at least has a contractual defense and some recourse...
Kayne's website, inc. details of his forthcoming book: kaynemcgladrey.com 
NEWS
McKesson Confirms Data Breach as Attacker Deadline Looms
Palo Alto Networks FY26 Q4, Earnings Results & Highlights
NetSPI and Synack to Merge
We welcome your feedback and suggestions, so please send us a message! Christina Richmond – christina@richmondadvisorygroup.com Rory Duncan – rory@richmondadvisorygroup.com Subscribe to our Newsletter - "Signal, not noise"Our monthly newsletter is free to subscribers! Sign-up now at Richmond Advisory Group.   Technology we use Podcast Recording Platform(s) – Cleanfeed & Riverside Cyber Sidekicks Show Host – Podbean Edited & mastered in GarageBand & Final Cut Pro