Threat modeling, penetration testing, and security design all share
a core discipline: thinking like an adversary. But adversarial
thinking isn't limited to cybersecurity—it applies anywhere you need
to anticipate failure modes, identify weak points, or stress-test systems.
This is my preferred method: always work backward from the objective.
Whether you're an attacker seeking data exfiltration, a defender
hardening infrastructure, or a cook ensuring flawless flan, the
questions remain the same.
Here’s a structured adversarial thinking template you can use across domains—security, debugging, marketing, design, even recipes. It’s built around my preferred method: always work backward from the goal/objective.
Step 1: Define the Desired Outcome
- What is the attacker’s (or evaluator’s) end state? (e.g., data theft, privilege escalation, flawless flan, successful campaign)
- What must be true for this outcome to exist? (e.g., credentials compromised, custard set, audience converted)
- What signals confirm success? (e.g., exfiltrated data, jiggle test, conversion metrics)
Step 2: Map Constraints and Affordances
- Affordances: What the system naturally makes easy?
- Constraints: What defenses or resistances exist?
- Ambiguities: Where policy and reality diverge?
Step 3: Work Backward Pathways
- Direct routes: Straightforward paths to the goal.
- Side channels: Indirect or overlooked paths.
- Combinatorics: Weak signals combined into strong outcomes.
- Pivot nodes: Small wins that unlock larger reach.
Step 4: Identify Choke Points
- Single points of failure: If broken, many paths collapse.
- Silent success indicators: Signs you’re close without alarms.
- Counterfactual probes: Actions that should change the system but don’t (revealing weak controls).
Step 5: Invert for Defense or Design
- Label motifs: Name recurring vulnerabilities (“Orphaned Authority,” “Ambient Secrets”).
- Publish refusals: Encode policies that kill entire classes of paths.
- Instrument choke points: Focus monitoring where backward paths converge.
- Pre-mortem drills: Assume breach, walk the graph, prove refusals hold.
🔍 Example: AWS S3 Bucket Data Exfiltration
Step 1 - Desired Outcome:
Attacker downloads sensitive customer data from S3 bucket.
Step 2 - Constraints & Affordances:
- Affordance: Public read access if misconfigured
- Constraint: IAM policies, bucket policies, encryption
- Ambiguity: "Temporarily public" buckets for staging
Step 3 - Backward Pathways:
- Direct: Compromised IAM credentials with s3:GetObject
- Side channel: Public bucket URL left in GitHub repo
- Pivot: Compromise EC2 with instance role → inherit S3 permissions
Step 4 - Choke Points:
- IAM policy evaluation (all paths flow through this)
- CloudTrail logging (silent success = no s3:GetObject logs)
- Bucket versioning (counterfactual: delete without versions disappearing)
Step 5 - Defensive Inversion:
- Motif: "Ambient Permissions" (overly broad IAM roles)
- Refusal: Explicit deny for s3:* on sensitive buckets unless MFA
- Instrument: Alert on any s3:GetObject from outside VPC
- Pre-mortem: Assume role compromised → prove refusal holds
Core Questions to Keep in Mind
- What is the end state I’m assuming?
- What must be true for that end state to exist?
- What are the affordances the system gives me?
- What are the constraints that resist me?
- What are the side channels or overlooked paths?
- Where are the pivot nodes that magnify small wins?
- What are the silent signals of success or failure?
- If I invert this path, what policy or refusal kills it?
- How do I prove inevitability or prove refusal?
🧾 Compact Template (Reusable)
Goal/Objective:
Invariants:
Affordances:
Constraints:
Backward Paths:
Choke Points:
Silent Signals:
Refusals:
Drill/Proof:
Top comments (1)
I’ve been wanting to do something genuinely different for a while, and I have this idea I’d love to run by you (and please, feel totally free to suggest, change, or remix anything—or just tell me if you’re not interested!).
The core concept:
We’d both post as a back-and-forth sequence—a kind of “Command Line Crossfire.” I’d share raw command-line outputs from my end (attacks, exploits, offensive moves), and you’d follow up with intelligence-style defense logs, case notes, or forensics showing your countermeasures and analysis. Each exchange would build up a kind of artifact archive, so people can see not just what happened, but how both sides interpret the same digital evidence. It’s half live incident, half public case file—unfolding for everyone to see.
Honestly, I have no idea if it’ll turn into something great or just be an absolute mess, but I do think it’d be unique, interesting, and a learning experience for both of us (and anyone watching). At the very least, it could inspire other people who want to see security research from both sides, not just the usual one-dimensional take.
And I totally get that reaching out like this in a comment isn’t the usual “play-by-play professional” move—maybe it’s even the opposite of how these things are normally done. But honestly, that’s kind of the point
If you’re interested, awesome—let’s brainstorm more. And if not, no worries at all.