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The library

Briefings. Short reads on the problems on your desk.

Written for the people running technology, finance, security, and compliance at PE-backed mid-market companies. Filter by problem, by where the company is in the ownership cycle, or by your role. Each briefing is a short analysis of a question executives are being asked.

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Briefing AI · Governance

What the board should be asking about AI before approving the budget.

Microsoft is promoting Copilot, and other software vendors have AI offers of their own. These reach the board as a budget line. A short list of questions helps the board decide.

For board, CEO, CIO May 2026 · 4 min read
Briefing Healthcare · Security

RC4 Kerberos in healthcare: HIPAA, cyber insurance, and clinical systems.

RC4 Kerberos raised HIPAA, cyber insurance, and clinical device questions for healthcare organizations. This briefing covers each, including where legacy systems prevented full enforcement.

For CIO, CCO, CISO May 2026 · 5 min read
Briefing AI

AI readiness and AI maturity are not the same thing.

AI readiness is whether your data, access controls, and policies can support AI safely. AI maturity is how far you have taken its use. Many organizations buy tools before they check readiness.

For CEO, CIO, CISO May 2026 · 4 min read
Briefing Security · Cyber Insurance

RC4 Kerberos and cyber insurance: what underwriters may ask for.

Insurers can ask for evidence of specific controls at underwriting and renewal, and some asked about RC4 Kerberos encryption. Requirements vary by carrier and policy. What underwriters may ask for, and what evidence can answer it.

For CFO, CIO, CISO May 2026 · 4 min read
Briefing Compliance · Security

Old Kerberos encryption (RC4) could create a compliance finding, whatever Microsoft's 2026 dates.

Whether active RC4 usage in Active Directory is a finding depends on which framework applies to you: HIPAA, PCI DSS, SOC 2, NIST 800-53, or CMMC. That did not depend on Microsoft's July 14, 2026 enforcement date.

For CCO, CISO, CFO May 2026 · 8 min read
Briefing AI · Governance

AI governance for Microsoft 365: what has to be true before you deploy Copilot.

Copilot respects the permissions you already have. Over-shared SharePoint sites, weak sensitivity labels, and gaps in data loss prevention policies carry straight into what Copilot can surface.

For CIO, CISO, CCO May 2026 · 8 min read
Briefing Security

If you delayed or rolled back the April 2026 Kerberos patch: what it meant.

Some IT teams delayed or rolled back the April 2026 Windows update after Kerberos failures. This briefing covers what each choice left exposed and the remediation sequence that followed.

For CIO, CISO May 2026 · 8 min read
Briefing Security

What the April 14, 2026 Windows update changed on domain controllers.

The April 14, 2026 update changed how domain controllers issue Kerberos tickets. The mechanism, the failure modes, and why a rollback did not fix every failure.

For CIO, CISO May 2026 · 10 min read

A note in your inbox when each one publishes.

We send a short note when a new briefing is published.