insecure-design

name

insecure-design

description

Detect, analyze, and remediate OWASP A06:2025 Insecure Design vulnerabilities in Python web applications (FastAPI and Flask). Use this skill whenever the user asks about architecture-level security flaws, threat modeling, rate limiting gaps, business logic vulnerabilities, insecure file uploads, race conditions, tenant isolation failures, or client-side enforcement of server-side security. Trigger even if the user doesn't say "Insecure Design" explicitly — common signals include: "missing rate limiting", "file upload security", "business logic flaw", "race condition", "multi-tenant isolation", "threat modeling", "STRIDE", "design review", or "can users abuse this flow". Also trigger for code reviews or audits where architecture-level security controls are being evaluated, not just implementation bugs.

OWASP A06:2025 — Insecure Design

What This Skill Does

Guides detection, analysis, and remediation of Insecure Design vulnerabilities — architecture-level failures where security controls are absent or structurally inadequate. Unlike implementation bugs, insecure design cannot be fixed by patching code alone; it requires redesigning the flow or adding missing control layers.

OWASP 2025 position: #6 (down from #4 in 2021, as threat modeling adoption has improved)
CWEs covered: 39 | Avg incidence: 1.86%
Key CWEs: CWE-434, CWE-269, CWE-362, CWE-799, CWE-602

---

Core Concepts

Design vs. Implementation

Insecure Design (A06)	Implementation Bug (other categories)
Rate limiting never architected into login flow	Rate limiter present but misconfigured
File upload stored in web root by design	Upload handler missing extension check
No tenant isolation in multi-tenant DB schema	Query missing WHERE clause
Business logic allows negative quantities	Missing server-side input validation

A design flaw requires adding a new control or refactoring the architecture, not just patching existing code.

---

Testing Checklist for FastAPI / Flask

1. Rate Limiting (CWE-799)

Verify that login, registration, password reset, and high-value transaction endpoints enforce rate limits.

FastAPI — SlowAPI:

from slowapi import Limiter
from slowapi.util import get_remote_address

limiter = Limiter(key_func=get_remote_address)

@app.post("/login")
@limiter.limit("5/minute")
async def login(request: Request, ...): ...

Flask — Flask-Limiter:

from flask_limiter import Limiter
limiter = Limiter(app, key_func=get_remote_address)

@app.route("/login", methods=["POST"])
@limiter.limit("5 per minute")
def login(): ...

Red flags to flag in review:

• Login, /register, /reset-password, /checkout routes with no rate-limiting decorator
• RATELIMIT_ENABLED = False or limiter initialized without being applied to sensitive routes
• Rate limits too permissive (e.g., 1000/minute on auth endpoints)

---

2. File Upload Security (CWE-434)

File uploads must be validated by content, not just extension, and stored outside the web root.

import magic  # python-magic

ALLOWED_MIME = {"image/jpeg", "image/png", "application/pdf"}
MAX_SIZE = 5 * 1024 * 1024  # 5 MB

@app.post("/upload")
async def upload(file: UploadFile):
    content = await file.read(MAX_SIZE + 1)
    if len(content) > MAX_SIZE:
        raise HTTPException(400, "File too large")
    mime = magic.from_buffer(content[:2048], mime=True)
    if mime not in ALLOWED_MIME:
        raise HTTPException(400, "Unsupported file type")
    # Store in /var/app/uploads/ — NOT inside static/ or public/
    safe_path = UPLOAD_DIR / secrets.token_hex(16)
    safe_path.write_bytes(content)

Red flags:

• Relying on file.content_type or extension alone (filename.endswith(".jpg"))
• Storing uploads in static/, public/, or any web-accessible path
• No file size cap
• Serving uploaded files via direct URL without authentication

---

3. Business Logic Flaws

Business logic flaws are application-specific — they exploit valid flows in unintended ways.

Common patterns to test:

Scenario	Test
Negative quantity in cart	POST with quantity: -1, verify order total doesn't go negative
Price manipulation	POST with a price field — verify server ignores client-supplied price
Concurrent purchase race	Parallel requests to buy last item — verify only one succeeds
Booking system abuse	Book same slot twice in parallel
Coupon reuse	Apply same coupon twice before first transaction commits

FastAPI example — safe quantity handling:

class OrderItem(BaseModel):
    product_id: int
    quantity: int = Field(..., ge=1, le=100)  # enforced server-side

Red flags:

• Price, discount, or role fields accepted from client payload
• No idempotency key or duplicate-check on financial transactions
• Quantity or amount not bounded with ge=1 in Pydantic or equivalent

---

4. Tenant Isolation (CWE-269)

In multi-tenant apps, every DB query must scope to the authenticated tenant.

Pattern to enforce:

# UNSAFE — returns data across all tenants
def get_reports(db: Session):
    return db.query(Report).all()

# SAFE — scoped to current tenant
def get_reports(db: Session, current_user: User):
    return db.query(Report).filter(Report.tenant_id == current_user.tenant_id).all()

Red flags:

• Any db.query(Model).all() without tenant/user filter
• Admin-like queries reachable from user-facing endpoints
• Tenant ID passed in request body (must come from JWT/session, not user input)

---

5. Client-Side Enforcement of Server-Side Security (CWE-602)

Security enforced only in the browser is trivially bypassed via direct API calls.

Red flags:

• Authorization check only in JavaScript / frontend, not in the API route
• Hidden form fields controlling price, role, or access level
• Feature flags based on client-provided values (use JWT claims or server session)

# WRONG — trusting client-supplied role
@app.post("/admin/action")
async def admin_action(role: str = Body(...)):  # never do this
    if role == "admin":
        ...

# CORRECT — derive from authenticated token
@app.post("/admin/action")
async def admin_action(current_user: User = Depends(get_current_user)):
    if current_user.role != "admin":
        raise HTTPException(403)
    ...

---

6. Credential / Account Recovery Design

Insecure recovery flows are a design flaw, not an implementation bug.

Red flags:

• Knowledge-based security questions (mother's maiden name, pet name) — guessable from social media
• Password reset link not expiring within 15–60 minutes
• Reset token sent over HTTP or stored without hashing
• Account enumeration possible via reset flow ("no account found" vs. silent success)

Safe pattern:

# Generate short-lived, single-use, high-entropy token
token = secrets.token_urlsafe(32)
expiry = datetime.utcnow() + timedelta(minutes=30)
# Store hash of token, not the token itself
db_token = PasswordResetToken(
    user_id=user.id,
    token_hash=hashlib.sha256(token.encode()).hexdigest(),
    expires_at=expiry,
    used=False
)

---

Threat Modeling Guidance (STRIDE)

Use STRIDE to find design flaws before they reach code:

Threat	Applies to	Example in FastAPI/Flask
Spoofing	Auth flows	Predictable session tokens, missing MFA
Tampering	Data in transit/storage	Missing HMAC on signed data, writable uploads
Repudiation	Audit logs	Missing request logging on financial actions
Information Disclosure	Error messages, API docs	/docs open in prod, stack traces in 500
Denial of Service	Rate limiting, resource use	No request size cap, missing rate limiter
Elevation of Privilege	Authorization design	Client-supplied role, missing tenant scope

---

Remediation Priority Matrix

Finding	Severity	Fix complexity
No rate limiting on auth/payment endpoints	High	Low — add SlowAPI/Flask-Limiter
File uploads stored in web root	High	Medium — move storage path, add serving layer
Client-supplied price/role fields	Critical	Low — remove field from request model
Missing tenant scope on DB queries	Critical	Medium — audit all queries
Knowledge-based security questions	Medium	High — redesign recovery flow
Race condition on inventory/booking	Medium	High — add DB-level locking or idempotency

---

Reference Material

For deeper dives, see:

• references/cwe-details.md — full CWE descriptions and examples for all 39 CWEs in A06
• references/threat-modeling.md — STRIDE worksheet template for FastAPI/Flask apps

For related OWASP categories that overlap with design issues:

• A01 Broken Access Control — when the design grants too much access by default
• A07 Authentication Failures — when auth flow design is the root cause
• A10 Mishandling of Exceptional Conditions — when error recovery design fails closed