What you're actually trying to prevent
The baseline controls
The deeper controls
Enforcement reality
- Build the compliance policies and put everything in report-only or "warn" mode
- Let it run for 2–4 weeks, review what's failing and why
- Fix the legitimate issues (old hardware, software conflicts, provisioning gaps)
- Enable Conditional Access enforcement for a pilot group
- Expand to full enforcement once the pilot is clean
Measuring it
- What percentage of managed endpoints pass compliance today? (Target: >95%)
- What are the top 3 reasons devices fail compliance?
- Are any devices passing compliance that shouldn't be (false compliant)?
- What's the DfE machine risk distribution across the fleet?
- When did the highest-risk device last check in?
Next: why I built Project Aegis — an AI agent system for security operations — and how the same Zero Trust principles apply to agentic systems that have access to sensitive tools.