FedRAMP 20X and the Automation of Arrested Development – TL;DR

After years in the trenches of cloud architecture, security assessments, and FedRAMP implementations, I can’t help but feel we’re missing the real opportunity to change. Automation is a tool, not a strategy. And if we use it to optimize the wrong process, we’re just accelerating our descent into compliance theater – now with APIs.

Let’s break this down.

Ask Better Questions

You can’t manage what you can’t measure, and you ought to make sure what you’re measuring is actually what you want to manage. So before automating anything, we should be asking:

What are we actually trying to achieve, and how did we get to where we are today?

FedRAMP exists to protect government systems by reducing risk – not by ensuring paperwork is properly formatted (either through digital PDFs or fancy configuration checks, whether automated or manual). So, if automation doesn’t measurably improve risk posture (let alone reduce the time, cost, and constraints of achieving it), it’s just fast bureaucracy.

Have we challenged the assumptions built into the current system?

• Why do we measure success with control compliance instead of resilience outcomes?
• Why do we force rigid standards (whether for controls or assessment reporting) and then act surprised when innovation dies?
• Are we optimizing what matters, or what we think is easy to quantify based on archaic paradigms?

It’s not what was proposed that’s bothersome. It’s what didn’t seem to get asked before it was proposed.

“Fools rush in where angels fear to tread.” In this case, fools automate what shouldn’t exist, then act surprised when it fails faster.

Steel-Manning the Automation Path

To be fair, FedRAMP 20X is trying to fix a very real problem: Manual assessments are slow, painful, and disconnected from reality.

So, the PMO wants to automate it – scanning configurations, streaming telemetry, and surfacing risk posture in near real-time. That’s admirable, and technically plausible. But even in a best-case scenario, this raises hard questions:

• Will every CSP now need to build custom evidence pipelines, posture dashboards, and agent infrastructure?
• If not, who does, and what are the CSP integration time and costs?
• Who maintains the “security of the audit system?”
• Will there still be time and cost of the auditors auditing the automated audit systems?
• What happens to small CSPs who can’t afford to build or integrate at that scale, or even larger CSP’s who aren’t positioned well to optimize things like CI/CD?
• Are we just building a more expensive, more complex version of the old GRC machine?

If we start to dig into these questions as we construct solutions (see my extended article), we quickly come to a few realizations:

• We shift costs, not eliminate them.
• We create flexibility on paper – but enforce rigidity through automation.
• We continue measuring compliance (now just in configuration format), not actual resilience.

This is a Greek tragedy in the making. Maybe we can rename the initiative to Oedipus 20X.

A Simpler, Similarly Radical, but More Serious Alternative

I once read a fortune cookie that said, “Great leaders are great simplifiers.”

Since radical proposals seem to be on the table, I have a different, even simpler, one. What if, instead of automating the paperwork and processes of checking for compliance…we eliminated the paperwork and compliance configuration checks all together?

In its place, we test. Like, REALLY test.

Resilience > Ritual

Test production systems through randomized, live red team exercises. If a CSP survives the test, they’re compliant. If not, they fix it and try again. No PDFs. No control-by-control justification. Just real proof of security under pressure.

Metrics That Matter

We track outcomes like:

• Breach frequency
• Time to detection
• Time to containment
• Fix durability
• Drift and regression

It’s chaos engineering for compliance – turning resilience into a measurable, continuous process.

Let CSPs Innovate

Want to use Kubernetes? Great.
Want to encrypt between clusters but not within? Fine.
Quantum entanglement and goat encryption? Be my guest.

As long as your system survives real-world attacks, you pass. No prescriptive architecture. No micromanaged policies. Just results.

Why This Works (and the Proposed FedRAMP 20X Path Doesn’t)

Compliance Automation:

Good – Reduces manual toil
Bad – Still assumes static controls = security
Bad – Penalizes non-standard tech stacks
Bad – Requires trust in telemetry over reality
Bad – Risk of massive cost bloat for minimal risk gain

Resilience Testing:

Good – Directly tests outcomes that matter (i.e., system and operational resilience to attacks)
Good – Promotes innovation
Good – Scales to any architecture
Good – Eliminates documentation burden
Good – Incentivizes real security, not theater

Final Thought

The real problem with FedRAMP isn’t just that it’s slow or expensive. These are merely symptoms of a deeper reality that we are generally focused on proving the wrong things. Automating a broken process doesn’t make it better. It just makes its failures faster and shinier.

So, before we go for innovation of automation, we need to consider innovation of thought.

Let’s stop building better paperwork in different formats.
Let’s start testing real security.

If all else fails though, there’s always money in the banana stand.

While we now live in a world of long-form podcasts, long-form reading still hasn’t caught on for many. If, however, you felt this was a bit too brief on important concepts, I’ve provided an extended version. In it you will find a deep dive around where we’re going wrong, detailed architectural options, shared responsibility models, and metric frameworks, click here for the full-length version of “FedRAMP 20X and the Automating of Arrested Development.”