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:
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