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Agentic Security Insights

Written by

Jason Rebholz

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Claude Cowork: A CISO's Guide to a Secure Rollout

Apr 19, 2026

•

4 min read

Claude Cowork: A CISO's Guide to a Secure Rollout

How to enable the workforce without destroying the company

Jason Rebholz
Jason Rebholz
Living-Off-the-Agent: An Attackers' New Best Friend

Apr 5, 2026

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6 min read

Living-Off-the-Agent: An Attackers' New Best Friend

Attackers next move will use your agents against you.

Jason Rebholz
Jason Rebholz
AI Roulette: How CISOs Can Stop Gambling on AI Security

Mar 29, 2026

•

6 min read

AI Roulette: How CISOs Can Stop Gambling on AI Security

CISOs have an impossible task with securing agents.

Jason Rebholz
Jason Rebholz
Part 2: A CISO's Guide to Securing Claude in the Enterprise

Mar 8, 2026

•

10 min read

Part 2: A CISO's Guide to Securing Claude in the Enterprise

Deploying Enterprise Security Controls for Claude

Jason Rebholz
Jason Rebholz
Agent Sandboxes Are a Public Beach

Feb 15, 2026

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7 min read

Agent Sandboxes Are a Public Beach

Why Agent Sandboxes aren't Effective Security Controls

Jason Rebholz
Jason Rebholz
Hidden Prompt Injection

Aug 31, 2025

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6 min read

Hidden Prompt Injection

Another way to bypass model security

Jason Rebholz
Jason Rebholz

Archive

Agentic Decompression Sickness

Apr 26, 2026

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3 min read

Agentic Decompression Sickness

Security teams used to get 20–30 years to catch up to a new computing era. With agents, we got two.

Jason Rebholz
Jason Rebholz
Claude Cowork: A CISO's Guide to a Secure Rollout

Apr 19, 2026

•

4 min read

Claude Cowork: A CISO's Guide to a Secure Rollout

How to enable the workforce without destroying the company

Jason Rebholz
Jason Rebholz
Anthropic's Managed Agents Overview

Apr 12, 2026

•

10 min read

Anthropic's Managed Agents Overview

A CISO's guide to understand what it is and how to secure it.

Jason Rebholz
Jason Rebholz
Living-Off-the-Agent: An Attackers' New Best Friend

Apr 5, 2026

•

6 min read

Living-Off-the-Agent: An Attackers' New Best Friend

Attackers next move will use your agents against you.

Jason Rebholz
Jason Rebholz
AI Roulette: How CISOs Can Stop Gambling on AI Security

Mar 29, 2026

•

6 min read

AI Roulette: How CISOs Can Stop Gambling on AI Security

CISOs have an impossible task with securing agents.

Jason Rebholz
Jason Rebholz
AI Security Risks: Paper Cuts Before Big Pain

Mar 22, 2026

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6 min read

AI Security Risks: Paper Cuts Before Big Pain

The small AI security incidents will add up quickly

Jason Rebholz
Jason Rebholz
Bad Intent: The Biggest Gap In AI Security

Mar 15, 2026

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8 min read

Bad Intent: The Biggest Gap In AI Security

Non-deterministic agents can defeat deterministic controls

Jason Rebholz
Jason Rebholz
Part 2: A CISO's Guide to Securing Claude in the Enterprise

Mar 8, 2026

•

10 min read

Part 2: A CISO's Guide to Securing Claude in the Enterprise

Deploying Enterprise Security Controls for Claude

Jason Rebholz
Jason Rebholz
Part 1: A CISO's Guide to Securing Claude in the Enterprise

Mar 1, 2026

•

5 min read

Part 1: A CISO's Guide to Securing Claude in the Enterprise

An overview of Claude's features

Jason Rebholz
Jason Rebholz
...
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