Intent Over Tactics: A CISO’s Guide to Protecting Your Crown Jewels

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Introduction

In an era of escalating cyber threats, security leaders often struggle with the overwhelming mandate to “secure everything.” Caleb Sima, a seasoned CISO and security executive, advocates for a strategic shift—focusing on protecting an organization’s “crown jewels” rather than chasing every potential vulnerability. His guide, Intent Over Tactics, provides a framework for prioritizing security efforts based on attacker intent, not just tactics.

Learning Objectives

  • Understand the “crown jewels” strategy for effective cybersecurity prioritization.
  • Learn how to identify and protect critical assets using attacker intent analysis.
  • Gain insights into measuring and communicating security success to stakeholders.

You Should Know

1. Identifying Your Crown Jewels

Before securing anything, you must define what’s most critical. Use data classification tools and threat modeling to identify high-value assets.

Command: Using `truffleHog` to Scan for Secrets in Git Repos 

trufflehog git --repo https://github.com/your-repo --only-verified

What This Does: Scans Git repositories for exposed secrets (API keys, passwords).

How to Use:

1. Install `truffleHog` via pip:

pip install trufflehog

2. Run against a target repo to detect leaked credentials.

3. Review findings and remediate exposed secrets.

2. Implementing Zero Trust for Crown Jewels

Once identified, enforce strict access controls using Zero Trust principles.

Command: Enforcing MFA in AWS IAM

aws iam create-virtual-mfa-device --virtual-mfa-device-name CrownJewelMFA --outfile QRCode.png --bootstrap-method QRCodePNG

What This Does: Configures Multi-Factor Authentication (MFA) for AWS IAM users.

How to Use:

1. Generate a virtual MFA device.

2. Distribute QR codes to users for enrollment.

  1. Enforce MFA via IAM policies for critical resources.
    1. Detecting Lateral Movement with Windows Event Logs
      Attackers often move laterally after initial access. Monitor Windows Event IDs for suspicious activity.

Command: Querying Suspicious Logon Events

Get-WinEvent -FilterHashtable @{LogName='Security'; ID=4624, 4625} | Where-Object { $_.Properties[bash].Value -eq '3' }

What This Does: Detects remote logins (RDP, network logins) which may indicate lateral movement.

How to Use:

1. Run in PowerShell on a Domain Controller.

2. Filter for Logon Type 3 (network logins).

3. Investigate unexpected remote sessions.

4. Hardening Kubernetes Clusters

If your crown jewels run in containers, Kubernetes security is critical.

Command: Checking for Misconfigured Pods

kubectl get pods --all-namespaces -o json | jq '.items[] | select(.spec.containers[].securityContext.privileged == true)'

What This Does: Finds privileged pods, which are a major security risk.

How to Use:

1. Install `jq` for JSON parsing.

  1. Audit and disable privileged containers unless absolutely necessary.

5. Automating Threat Detection with Sigma Rules

Instead of chasing every alert, use Sigma rules to detect attacker intent.

Example Sigma Rule for Ransomware Activity

title: Suspicious File Encryption Activity 
description: Detects mass file encryption (ransomware behavior) 
logsource: 
product: windows 
service: security 
detection: 
selection: 
EventID: 4656 
ObjectType: File 
AccessMask: '0x2' 
condition: selection

What This Does: Triggers alerts when files are modified en masse.

How to Use:

  1. Deploy in a SIEM like Splunk or Elastic.

2. Tune to reduce false positives.

What Undercode Say

  • Key Takeaway 1: Focus on attacker intent—what they want, not just how they get it.
  • Key Takeaway 2: Measure success by % of crown jewels protected, not just vulnerability counts.

Analysis:

Caleb Sima’s approach aligns with modern security frameworks like MITRE ATT&CK, emphasizing detection over prevention. By prioritizing crown jewels, CISOs can allocate limited resources effectively. The shift from “secure everything” to risk-based defense is critical in an era of AI-driven attacks.

Prediction

As AI-powered attacks increase, the crown jewels strategy will become the standard for enterprise security. Organizations that fail to adopt intent-based defense will face higher breach costs due to inefficient resource allocation.

For more insights, read Caleb Sima’s full guide: Intent Over Tactics.

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