AI Governance Hurdles in Defense: Jason Tierney Examines CMMC Barriers for MSPsThe episode details a tightening regulatory environment driven by new enforcement timelines for Cybersecurity Maturity Model... By: Dave Sobel/May 26, 2026/Artificial Intelligence, Community Sentiment, Guest Interviews, Regulation, Security
MSPs Are Getting Breached, and Clients Are Already Planning to LeaveBreach, Then SwitchThe observable shift starts with four facts showing up at the same time: MSPs... By: Dave Sobel/May 20, 2026/Artificial Intelligence, Business Strategy, Community Sentiment, Product & Company Updates, Regulation, Security
Unmanaged AI Participants Are Creating Records, Liability, and Audit Gaps MSPs Don’t Own YetAgents UncheckedWIRED has a new, ugly data point on what happens when “anyone can ship software... By: Dave Sobel/May 12, 2026/Artificial Intelligence, Business Strategy, Regulation, Security
AI Consumption Billing Creates Accountability Gap in MSP ContractsAI Bill DueStart with Microsoft. In late April, BleepingComputer reported that admins can now remove the... By: Dave Sobel/May 8, 2026/Artificial Intelligence, Business Strategy, Community Sentiment, Product & Company Updates, Regulation
AI Agents Shift MSP Accountability From Support to Operator of RecordAgents Gone RogueWe’re seeing a cluster of public signals that AI is moving from “advice” to... By: Dave Sobel/May 6, 2026/Artificial Intelligence, Product & Company Updates, Regulation, Security
AI Compresses Exploit Windows While MSPs Still Price Security as Best EffortAI Patches GapsWe’ll start with federal confirmation. The Hacker News reports that CISA has added two... By: Dave Sobel/May 1, 2026/Artificial Intelligence, Business Strategy, Regulation, Security
The Pivotal Point of IT: Building Services for the AI-First EraShadow AI RiskWe’re seeing a clear pattern in how generative AI is colliding with security and... By: Dave Sobel/April 24, 2026/Artificial Intelligence, Community Sentiment, Regulation, Security
Proof Replaces Tools as Core MSP Value as Governance Becomes a Delivery ObligationSovereignty SqueezeStart in Europe. France’s Interministerial Digital Directorate is ordering government ministries to move workstations off... By: Dave Sobel/April 22, 2026/Artificial Intelligence, Business Strategy, Regulation, Security
AI Collapsing the Software Layer: Risks for MSP Roles and Tech Debt with Dusty GullesonThe episode focuses on the ongoing collapse of traditional software and service delivery layers, accelerated by... By: Dave Sobel/April 13, 2026/Artificial Intelligence, Business Strategy, Community Sentiment, Regulation
From Peer Review to Outage Reports: AI Accountability Becomes Operational InfrastructureThe Visibility Problem The signal is that AI use is becoming visible to institutions in ways... By: Dave Sobel/April 8, 2026/Artificial Intelligence, Business Strategy, Community Sentiment, Product & Company Updates, Regulation, Security
Automation Exposes Coordination Debt—MSPs Must Govern It or Absorb ItAutomation Divide AI use is spreading, but readiness is uneven, and the operational expectations around speed... By: Dave Sobel/April 7, 2026/Artificial Intelligence, Business Strategy, Regulation, Security
Compliance Now Drives Tech Selection: FCC Router Ban and AI Procurement Terms Shift MSP LiabilityContract Conditions Policy is starting to behave less like a guardrail and more like a steering... By: Dave Sobel/March 24, 2026/Artificial Intelligence, Business Strategy, Regulation, Security
How Cyber Insurance Analytics Are Changing Risk Accountability for MSPs – Nir Perry of CyberwriteThe episode highlights a structural shift in the cyber insurance market, marked by increasing reliance on... By: Dave Sobel/March 19, 2026/Artificial Intelligence, Business Strategy, Regulation, Security
The Pentagon Didn’t Just Drop Claude—It Proved the Model Is Now a Managed DependencyPentagon vs. Anthropic As I’ve covered previously, Anthropic had their contract with the Pentagon cancelled, and... By: Dave Sobel/March 16, 2026/Artificial Intelligence, Business Strategy, Product & Company Updates, Regulation
AI Cost Shifting Forces MSPs to Price Governance as Managed Risk, Not Add-OnROI Reality Check A recent study shows only 4% of businesses see ROI from AI, with... By: Dave Sobel/March 11, 2026/Artificial Intelligence, Community Sentiment, Product & Company Updates, Regulation, Security
Anthropic Blacklisted After Rejecting Pentagon’s Autonomous Weapons Data DemandsOn Friday, President Donald Trump directed federal agencies to cease using Anthropic’s artificial intelligence technology, signaling... By: Dave Sobel/March 3, 2026/Artificial Intelligence, Regulation
Anthropic Refuses Pentagon Demands on Surveillance and Autonomous Weapons, Risks ContractDario Amodei, CEO of Anthropic, responded to the Department of Defense demands (which I covered yesterday)... By: Dave Sobel/February 27, 2026/Artificial Intelligence, Regulation
CISA Cuts, Azure Sovereignty Push Signal End of Federal MSP Safety NetThe U.S. House of Representatives has passed the Small Business Artificial Intelligence Advancement Act, which aims... By: Dave Sobel/February 26, 2026/Regulation
AI Compliance Tools Flood Market as MSPs Face Validation GapCompliance Scorecard has released version 10 of its platform, which introduces new features, including AI that... By: Dave Sobel/February 26, 2026/Product & Company Updates, Regulation, Security
Most Security Chiefs Say They’re Not Ready for AI-Powered Cyberattacks Coming This YearA recent report from LevelBlue reveals that only 53% of Chief Information Security Officers, or CISOs,... By: Dave Sobel/February 12, 2026/Regulation