When Patching Can’t Keep Up
What PHP2Shell and Railway show about service disruption and the access that can survive a patch.
The operating side of Digital Trust & AI.
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Who Patches While You Sleep?
I joined Sam Rogers to talk about what happened when I checked my own automated security stack and found that most of it had stopped working without telling me. We discussed how to know what’s actually running, how to give agents clear boundaries, and where to start with the Daily Patch Loop.
New · AI tools
Take control of your AI stack’s security posture.
The Daily Patch Loop is a prompt for your own agent. Every day it matches new attacks and vulnerabilities to your AI tools, local systems and apps, repos and web apps. It checks each fix against your trust policy, changes only what you authorize, and tells you what it can’t fix yet.
Four connected subjects
Make trust work
in your environment.
Practical guides, field notes, and questions for your team. A personal perspective on the decisions that connect these subjects.
Device & machine identity
Identify, update, isolate, and recover the systems you operate.
Explore this subjectSoftware assurance
Connect product evidence with what buyers and regulators need.
Explore this subjectCryptographic change
Find the dependencies before certificates and algorithms change.
- PQC readiness: the first five actions
- PQC migration: build the ability to change cryptography
- PKI operations: from renewal alerts to a managed service
AI trust in practice
Know what an agent can do, what constrains it, and what can be proved.
Explore this subjectThe dates do not move
The Forcing Function Calendar
The regulatory deadlines and standards transitions reshaping enterprise digital trust between 2026 and 2030. Know what is adopted, who it affects, and what to ask your team.
Cyber Resilience Act reporting begins
Manufacturers must report actively exploited vulnerabilities and severe security incidents. Early warning is due within 24 hours of awareness; the next notification is due within 72 hours. Final reports follow separate clocks.
Existing AI systems: content-marking transition ends
Certain providers of synthetic-content AI systems placed on the market before 2 August 2026 must meet Article 50(2) marking requirements by this date.
CNSA 2.0 enters new NSS acquisitions
New acquisitions for U.S. National Security Systems must be CNSA 2.0 compliant unless an exception applies. Deployment requirements also depend on the relevant validation profile.
Reviewed September 2026 · Quarterly review cadence · Primary sources linked in the full calendar.
Guides & resources
Take the question
into the field.
Practical reading from the archive, with questions and frameworks to use in your own environment.
Can You Revoke One Device Without Breaking the Fleet?
A starting point for testing whether one compromised device can be isolated without disrupting the rest of the fleet.
If You Use Public Certificates for mTLS, Start Looking Now
Find where public certificates are used for client authentication, and identify what needs to change.
Hardening Claude Code: A Security Review Framework and the Prompt That Does It For You
A security review framework and reusable prompt for examining an AI coding assistant’s access.
About Tim
Technical depth.
A field perspective.
I’m Regional Field CTO at DigiCert. My work connects PKI, device identity, software assurance, and AI with the engineering and operating decisions organizations face.
This is my personal publication. Views are my own.
More about my workSpeaking & collaboration
Bring the conversation
to your team.
Keynotes, panels, and workshops on device trust, cryptographic change, software assurance, and the authority we give AI systems.
Past speaking includes Embedded World, CES, and RSA Conference.