TLDR IT 2026-05-13
The Agent Mess Gets Real 🤖, Cyber Gets Autonomous ⚔️, Cloud’s New Pitch 🏗️
The State of IT has fundamentally changed in 2026: read the full report HERE (Sponsor)
We spent months interviewing IT leaders who are actively building the AI-era playbook at Cloudflare, Cursor, Lyft, GitLab, Nextdoor, Zip, Rubrik, Zscaler and Palo Alto Network, among others. Read the playbook that includes:
- The growth case for AI
- Running 90 day pilots, not 12-month RFPs
- Why it's IT's time to build
- The emergence of the IT engineer
Teams running this playbook are tracking toward delivering 40% of business initiative needs. Most IT organizations deliver 15% to 20% today.Download The State of IT 2026: the first research report on what the highest-performing IT organizations are building, and how.
Canvas Owner Cuts Deal After Double Breach (3 minute read)
Instructure, the company behind Canvas, reached a deal with hackers who breached its systems twice and stole large amounts of student and staff data. The company said the agreement is intended to prevent the stolen information from being published, making the incident a sharp example of how breach response increasingly includes negotiation with attackers, not just remediation.
Checkmarx Jenkins plugin compromised in new supply chain attack (3 minute read)
The Checkmarx Jenkins AST plugin version 2026.5.09 is compromised by TeamPCP, carrying a 9.4 CVSS score (CVE-2026-33634). Attackers targeted cloud credentials and SSH keys. Users must immediately downgrade to version 2.0.13-829.vc72453fa_1c16 and rotate all exposed secrets to mitigate potential unauthorized access to enterprise environments.
OpenAI Launches Daybreak for Cyber Defense (4 minute read)
Daybreak is a cybersecurity initiative from OpenAI that uses LLMs, Codex agentic capabilities, and partners like Cloudflare, Cisco, CrowdStrike, Oracle, and Zscaler to find and help patch vulnerabilities. The product is publicly available for companies to request security-risk assessments, positioning OpenAI directly against Anthropic's Mythos-style cyber models.
GitLab Restructures for the Agentic Era (5 minute read)
GitLab announced a restructuring tied to its “agentic era” strategy, including flattening parts of the org, reorganizing R&D into roughly 60 smaller teams, and embedding AI agents into internal reviews, approvals, and handoffs. CEO Bill Staples framed the shift around software increasingly being “built by machines, directed by people,” with humans still owning architecture, judgment, and customer understanding.
AI Usage Metrics Start Getting Gamed (4 minute read)
Employees at Amazon, Meta, and Microsoft have reportedly gamed internal AI usage metrics, with some Amazon workers using tools unnecessarily to increase token usage. The story highlights a growing enterprise problem: measuring AI adoption by activity can incentivize performative usage instead of real productivity gains.
How Superset built the IDE for AI agents on Vercel (4 minute read)
Superset, an IDE for multi-agent development, leverages Vercel to manage 1,000–1,400 weekly deployments and 600 daily preview environments. By utilizing Vercel's fluid compute and automated infrastructure, the team enables parallel coding agents to operate without serialization delays, maintaining 30-second build times and supporting exponential commit growth.
Versa takes aim at fragmented enterprise security with CSPM orchestration update and AI agent controls (6 minute read)
Versa launched new CSPM capabilities to pull cloud misconfiguration visibility into its broader SASE platform, reducing the need to jump between separate security tools. Its upcoming framework for controlling AI agents before they can autonomously change policies or infrastructure configs is yet another sign that agent governance is quickly becoming a real enterprise security category.
Curated news 🗞️ and trends 📈 in IT strategy 💻, information security 🔐, and cloud computing ☁️.
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