Sharp Edges

Trail of BitsOfficialPublished by Trail of Bits

Skill
Guidelines
Security
CC-BY-SA-4.0
Medium risk

From the author

Identifies error-prone APIs, dangerous configurations, and footgun designs that enable security mistakes. Use when reviewing API designs, configuration schemas, cryptographic library ergonomics, or evaluating whether code follows 'secure by default' and 'pit of success' principles. Triggers: footgun, misuse-resistant, secure defaults, API usability, dangerous configuration.

— the description by Trail of Bits

AutoGineer summary

Written by AutoGineer from the skill’s own files, not by the author

Sharp Edges is a systematic analysis framework designed to identify 'footguns'—design patterns in APIs, libraries, and configurations that make it easy for developers to inadvertently introduce security flaws. By focusing on the 'pit of success' principle, this skill helps auditors and developers ensure that the path of least resistance is also the most secure one. It provides a structured workflow to probe for common pitfalls like weak algorithm selection, insecure defaults, silent failures, and type confusion, moving beyond simple bug hunting to address the root causes of developer-induced security mistakes.

What it does

Maps security-relevant APIs and configuration schemas for potential misuse.
Probes for edge cases like zero, null, or negative values that bypass security logic.
Evaluates whether default settings are secure by design.
Identifies cryptographic and authentication patterns prone to developer error.
Assesses the risk of silent failures and stringly-typed security interfaces.
Classifies findings by severity based on how easily a developer can trigger a vulnerability.

When to use it

During the design phase of new APIs or configuration schemas.
When auditing cryptographic library ergonomics and usage patterns.
When reviewing authentication and authorization interfaces.
When assessing whether code follows secure-by-default principles.
When evaluating the impact of developer-facing configuration options.

Advantages

Focuses on design-level flaws rather than just implementation bugs.
Promotes the 'pit of success' by identifying where secure usage is difficult.
Provides a repeatable, four-phase workflow for consistent analysis.
Helps prevent common security mistakes like algorithm confusion and insecure defaults.
Encourages the creation of misuse-resistant APIs.

Usage examples

“Analyze this authentication library for potential sharp edges.”: The agent will identify if the library allows empty passwords, uses predictable token generation, or has insecure default session timeouts.
“Review this configuration schema for dangerous options.”: The agent will flag boolean flags that disable security, unvalidated constructor parameters, or magic values that could lead to catastrophic failure.

Install

Download the skill as a ZIP:
https://mp-staging.autogineer.com/agent-skills/trailofbits/sharp-edges/download

Unzip it into the cross-client skills folder of your project:

mkdir -p .agents/skills && unzip sharp-edges.zip -d .agents/skills

Documentation by Trail of Bits

Sharp Edges Analysis

Evaluates whether APIs, configurations, and interfaces are resistant to developer misuse. Identifies designs where the "easy path" leads to insecurity.

When to Use

Reviewing API or library design decisions
Auditing configuration schemas for dangerous options
Evaluating cryptographic API ergonomics
Assessing authentication/authorization interfaces
Reviewing any code that exposes security-relevant choices to developers

When NOT to Use

Implementation bugs (use standard code review)
Business logic flaws (use domain-specific analysis)
Performance optimization (different concern)

Agent

The sharp-edges-analyzer agent runs the full sharp edges analysis workflow autonomously. Use it when you want a dedicated analysis of APIs, configurations, or interfaces for misuse resistance and footgun potential. The agent follows the four-phase workflow (Surface Identification, Edge Case Probing, Threat Modeling, Validate Findings) and reads language-specific references on demand.

Core Principle

The pit of success: Secure usage should be the path of least resistance. If developers must understand cryptography, read documentation carefully, or remember special rules to avoid vulnerabilities, the API has failed.

Rationalizations to Reject

Rationalization	Why It's Wrong	Required Action
"It's documented"	Developers don't read docs under deadline pressure	Make the secure choice the default or only option
"Advanced users need flexibility"	Flexibility creates footguns; most "advanced" usage is copy-paste	Provide safe high-level APIs; hide primitives
"It's the developer's responsibility"	Blame-shifting; you designed the footgun	Remove the footgun or make it impossible to misuse
"Nobody would actually do that"	Developers do everything imaginable under pressure	Assume maximum developer confusion
"It's just a configuration option"	Config is code; wrong configs ship to production	Validate configs; reject dangerous combinations
"We need backwards compatibility"	Insecure defaults can't be grandfather-claused	Deprecate loudly; force migration

Sharp Edge Categories

1. Algorithm/Mode Selection Footguns

APIs that let developers choose algorithms invite choosing wrong ones.

The JWT Pattern (canonical example):

Header specifies algorithm: attacker can set "alg": "none" to bypass signatures
Algorithm confusion: RSA public key used as HMAC secret when switching RS256→HS256
Root cause: Letting untrusted input control security-critical decisions

Detection patterns:

Function parameters like algorithm, mode, cipher, hash_type
Enums/strings selecting cryptographic primitives
Configuration options for security mechanisms

Example - PHP password_hash allowing weak algorithms:

// DANGEROUS: allows crc32, md5, sha1
password_hash($password, PASSWORD_DEFAULT); // Good - no choice
hash($algorithm, $password); // BAD: accepts "crc32"

2. Dangerous Defaults

Defaults that are insecure, or zero/empty values that disable security.

The OTP Lifetime Pattern:

# What happens when lifetime=0?
def verify_otp(code, lifetime=300):  # 300 seconds default
    if lifetime == 0:
        return True  # OOPS: 0 means "accept all"?
        # Or does it mean "expired immediately"?

Detection patterns:

Timeouts/lifetimes that accept 0 (infinite? immediate expiry?)
Empty strings that bypass checks
Null values that skip validation
Boolean defaults that disable security features
Negative values with undefined semantics

Questions to ask:

What happens with timeout=0? max_attempts=0? key=""?
Is the default the most secure option?
Can any default value disable security entirely?

3. Primitive vs. Semantic APIs

APIs that expose raw bytes instead of meaningful types invite type confusion.

The Libsodium vs. Halite Pattern:

// Libsodium (primitives): bytes are bytes
sodium_crypto_box($message, $nonce, $keypair);
// Easy to: swap nonce/keypair, reuse nonces, use wrong key type

// Halite (semantic): types enforce correct usage
Crypto::seal($message, new EncryptionPublicKey($key));
// Wrong key type = type error, not silent failure

Detection patterns:

Functions taking bytes, string, []byte for distinct security concepts
Parameters that could be swapped without type errors
Same type used for keys, nonces, ciphertexts, signatures

The comparison footgun:

// Timing-safe comparison looks identical to unsafe
if hmac == expected { }           // BAD: timing attack
if hmac.Equal(mac, expected) { }  // Good: constant-time
// Same types, different security properties

4. Configuration Cliffs

One wrong setting creates catastrophic failure, with no warning.

Detection patterns:

Boolean flags that disable security entirely
String configs that aren't validated
Combinations of settings that interact dangerously
Environment variables that override security settings
Constructor parameters with sensible defaults but no validation (callers can override with insecure values)

Examples:

# One typo = disaster
verify_ssl: fasle  # Typo silently accepted as truthy?

# Magic values
session_timeout: -1  # Does this mean "never expire"?

# Dangerous combinations accepted silently
auth_required: true
bypass_auth_for_health_checks: true
health_check_path: "/"  # Oops

// Sensible default doesn't protect against bad callers
public function __construct(
    public string $hashAlgo = 'sha256',  // Good default...
    public int $otpLifetime = 120,       // ...but accepts md5, 0, etc.
) {}

See config-patterns.md for detailed patterns.

5. Silent Failures

Errors that don't surface, or success that masks failure.

Detection patterns:

Functions returning booleans instead of throwing on security failures
Empty catch blocks around security operations
Default values substituted on parse errors
Verification functions that "succeed" on malformed input

Examples:

# Silent bypass
def verify_signature(sig, data, key):
    if not key:
        return True  # No key = skip verification?!

# Return value ignored
signature.verify(data, sig)  # Throws on failure
crypto.verify(data, sig)     # Returns False on failure
# Developer forgets to check return value

6. Stringly-Typed Security

Security-critical values as plain strings enable injection and confusion.

Detection patterns:

SQL/commands built from string concatenation
Permissions as comma-separated strings
Roles/scopes as arbitrary strings instead of enums
URLs constructed by joining strings

The permission accumulation footgun:

permissions = "read,write"
permissions += ",admin"  # Too easy to escalate

# vs. type-safe
permissions = {Permission.READ, Permission.WRITE}
permissions.add(Permission.ADMIN)  # At least it's explicit

Analysis Workflow

Phase 1: Surface Identification

Map security-relevant APIs: authentication, authorization, cryptography, session management, input validation
Identify developer choice points: Where can developers select algorithms, configure timeouts, choose modes?
Find configuration schemas: Environment variables, config files, constructor parameters

Phase 2: Edge Case Probing

For each choice point, ask:

Zero/empty/null: What happens with 0, "", null, []?
Negative values: What does -1 mean? Infinite? Error?
Type confusion: Can different security concepts be swapped?
Default values: Is the default secure? Is it documented?
Error paths: What happens on invalid input? Silent acceptance?

Phase 3: Threat Modeling

Consider three adversaries:

The Scoundrel: Actively malicious developer or attacker controlling config
- Can they disable security via configuration?
- Can they downgrade algorithms?
- Can they inject malicious values?
The Lazy Developer: Copy-pastes examples, skips documentation
- Will the first example they find be secure?
- Is the path of least resistance secure?
- Do error messages guide toward secure usage?
The Confused Developer: Misunderstands the API
- Can they swap parameters without type errors?
- Can they use the wrong key/algorithm/mode by accident?
- Are failure modes obvious or silent?

Phase 4: Validate Findings

For each identified sharp edge:

Reproduce the misuse: Write minimal code demonstrating the footgun
Verify exploitability: Does the misuse create a real vulnerability?
Check documentation: Is the danger documented? (Documentation doesn't excuse bad design, but affects severity)
Test mitigations: Can the API be used safely with reasonable effort?

If a finding seems questionable, return to Phase 2 and probe more edge cases.

Severity Classification

Severity	Criteria	Examples
Critical	Default or obvious usage is insecure	`verify: false` default; empty password allowed
High	Easy misconfiguration breaks security	Algorithm parameter accepts "none"
Medium	Unusual but possible misconfiguration	Negative timeout has unexpected meaning
Low	Requires deliberate misuse	Obscure parameter combination

References

By category:

Cryptographic APIs: See references/crypto-apis.md
Configuration Patterns: See references/config-patterns.md
Authentication/Session: See references/auth-patterns.md
Real-World Case Studies: See references/case-studies.md (OpenSSL, GMP, etc.)

By language (general footguns, not crypto-specific):

Language	Guide
C/C++	references/lang-c.md
Go	references/lang-go.md
Rust	references/lang-rust.md
Swift	references/lang-swift.md
Java	references/lang-java.md
Kotlin	references/lang-kotlin.md
C#	references/lang-csharp.md
PHP	references/lang-php.md
JavaScript/TypeScript	references/lang-javascript.md
Python	references/lang-python.md
Ruby	references/lang-ruby.md

See also references/language-specific.md for a combined quick reference.

Quality Checklist

Before concluding analysis:

[ ] Probed all zero/empty/null edge cases
[ ] Verified defaults are secure
[ ] Checked for algorithm/mode selection footguns
[ ] Tested type confusion between security concepts
[ ] Considered all three adversary types
[ ] Verified error paths don't bypass security
[ ] Checked configuration validation
[ ] Constructor params validated (not just defaulted) - see config-patterns.md

Files

ATTRIBUTION.mdAdded by AutoGineer927 B
LICENSELicence file added by AutoGineer19.7 KiB
SKILL.md11.5 KiB
agents/openai.yaml239 B
assets/trail-of-bits-mark.svg3.0 KiB
references/auth-patterns.md6.8 KiB
references/case-studies.md8.0 KiB
references/config-patterns.md9.5 KiB
references/crypto-apis.md5.2 KiB
references/lang-c.md5.5 KiB
references/lang-csharp.md7.2 KiB
references/lang-go.md6.5 KiB
references/lang-java.md6.7 KiB
references/lang-javascript.md6.8 KiB
references/lang-kotlin.md6.6 KiB
references/lang-php.md6.0 KiB
references/lang-python.md6.5 KiB
references/lang-ruby.md6.1 KiB
references/lang-rust.md6.4 KiB
references/lang-swift.md6.1 KiB
references/language-specific.md13.0 KiB

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Requirements and compatibility

Works with: Claude Code, Claude apps, OpenAI Codex, GitHub Copilot, Cursor, Gemini CLI, Kiro, OpenCode, Goose, Amp, Roo Code, JetBrains Junie, Factory Droid, Devin (ex-Windsurf), Mistral Vibe, OpenHands, Letta

“Works with” means the tool reads the open Agent Skills format; a skill written for one tool may use features others lack.

Needs: Declares allowed tools, Needs Python

Security

What our scanner noticed· Medium risk

References to credential files

A static scan is not a guarantee. Skills are third-party content: review a skill before you let an agent use it.

Attribution and licence

Published by

Trail of Bits

Publisher

Trail of Bits (Official)

Source

trailofbits/skills · plugins/sharp-edges/skills/sharp-edges · commit e4dd0bb

Licence

Creative Commons Attribution-ShareAlike 4.0 International (redistribution allowed)

LICENSE (added by AutoGineer from LICENSE)
ATTRIBUTION.md (written by AutoGineer)

Synced

2026-11-08

AutoGineer is not affiliated with or endorsed by Trail of Bits.

Download ZIP

The ZIP holds the skill’s files, its licence files and an ATTRIBUTION.md. Download sharp-edges.zip

From the author

AutoGineer summary

What it does

When to use it

Advantages

Usage examples

Install

Documentation by Trail of Bits

Sharp Edges Analysis

When to Use

When NOT to Use

Agent

Core Principle

Rationalizations to Reject

Sharp Edge Categories

1. Algorithm/Mode Selection Footguns

2. Dangerous Defaults

3. Primitive vs. Semantic APIs

4. Configuration Cliffs

5. Silent Failures

6. Stringly-Typed Security

Analysis Workflow

Phase 1: Surface Identification

Phase 2: Edge Case Probing

Phase 3: Threat Modeling

Phase 4: Validate Findings

Severity Classification

References

Quality Checklist

Files

LICENSE

Requirements and compatibility

Security

Attribution and licence

Related skills

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Sast Configuration

Firmware Analyst

Policy Enforcer

Backend Development Security Auditor

Memory Forensics

Download ZIP