Brent Gifford
30-year CIO/CISO. Two newsletters: the Digital Safety Playbook — plain-English online safety for everyday people (scams, fake stores, protecting your accounts and family) — and the CIO & CISO Executive Brief, governance for security leaders.
| Platform |  | Pricing | Only free issues | Publishes | Daily |
|---|---|---|---|---|---|
| Issues | 81 | Founded | 9 months ago | Last Issue | 7 days ago |
| Active | |||||
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brentdgifford.substack.comLatest Issues
CIO Executive Brief #38 — Your Developers Already Made the Decision
TL;DR
· The decision about what company data an AI may see is being made one person at a time, by people acting in good faith, at the moment a permission prompt appears.
· This is not shadow IT in the old sense. Nobody is evading a rul...
CISO Executive Brief #38 — The Feature You Never Bought
TL;DR
· An AI coding tool your organization already approved can now periodically photograph the developer’s screen. There was no procurement event, no contract change, and no vulnerability — the capability arrived in a product update....
CIO Executive Brief #37 — Implementation Is Not Transformation
TL;DR
· Most AI programs are implementations wearing the language of transformation. The technology is new, the process it runs is not, and nobody examined the process before automating it — so the organization gets the same work, faster,...
CISO Executive Brief #37 — When the Control Plane Trusts an Attacker
TL;DR
· Between February and June, Cisco’s Catalyst SD-WAN management stack accumulated four KEV-listed vulnerabilities under active exploitation. The one that matters most is CVE-2026-20182, a CVSS 10.0 authentication bypass in the SD-WAN...
CIO Executive Brief #36 — Adjudication Is the Constraint
TL;DR
· Every AI deployment in the technology function increases the volume of things requiring a human decision while leaving unchanged the number of humans who can make those decisions. The work AI removes and the work it creates are dif...
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30-year CIO/CISO. Two newsletters: the Digital Safety Playbook — plain-English online safety for everyday people (scams, fake stores, protecting your accounts and family) — and the CIO & CISO Executive Brief, governance for security leaders.
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