Security Misconfiguration

Security Misconfiguration (OWASP A02:2025)

Security Misconfiguration leapt from #5 to #2 in the OWASP Top 10:2025, found in 3.00% of applications with over 719,000 occurrences. It occurs when systems are incorrectly configured from a security perspective — and in Python web apps, the attack surface is wide.

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Workflow

1. Identify the framework — Flask, FastAPI, or both
2. Run static checks — Bandit SAST scan (see Tooling section)
3. Walk the checklist — go through each category below, flag issues
4. Generate a report — list findings with CWE IDs, severity, and remediation snippets
5. Verify fixes — re-run Bandit + dynamic header scan after remediation

For deep dives into any single category, read:

• references/flask-hardening.md — Flask-specific settings and extensions
• references/fastapi-hardening.md — FastAPI-specific settings and middleware
• references/security-headers.md — Full header reference with CSP examples

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Checklist by Category

1. Debug Mode Exposed (Critical)

Flask

# BAD — never in production
app.run(debug=True)
app = Flask(__name__, debug=True)

# BAD — environment variable
# FLASK_DEBUG=1

# GOOD
app.run(debug=False)
# or: rely on FLASK_ENV=production (Flask 2.x) / FLASK_DEBUG=0

• Werkzeug's interactive debugger allows arbitrary code execution via PIN bypass
• Bandit rule: B201 (flaskdebugtrue)

FastAPI — has no debug mode equivalent but /docs and /redoc exposure is analogous (see §3)

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2. Hardcoded Secrets (Critical)

Detect patterns:

# BAD
SECRET_KEY = "supersecretkey123"
DATABASE_URL = "postgresql://user:password@host/db"
JWT_SECRET = "my-jwt-secret"
AWS_SECRET_ACCESS_KEY = "wJalrXUtnFEMI/K7MDENG/bPxRfiCYEXAMPLEKEY"

Correct approach:

import os
SECRET_KEY = os.environ["SECRET_KEY"]          # raises if missing — intentional
DATABASE_URL = os.environ.get("DATABASE_URL")  # or use python-dotenv / pydantic-settings

• Bandit rule: B105, B106, B107 (hardcodedpassword*)
• Also flag: secrets committed to .env files checked into version control
• Key CWEs: CWE-526 (Sensitive Info in Env Vars), CWE-321 (Hard-coded Crypto Key)

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3. Exposed API Documentation (High)

FastAPI — /docs (Swagger UI) and /redoc must be disabled in production:

# BAD — default behaviour exposes full API schema
app = FastAPI()

# GOOD — disable in production
import os
docs_url = None if os.getenv("ENV") == "production" else "/docs"
redoc_url = None if os.getenv("ENV") == "production" else "/redoc"
app = FastAPI(docs_url=docs_url, redoc_url=redoc_url)

• If docs must be kept, protect behind auth middleware or IP allowlist
• Also flag: Flask flask-swagger-ui or flasgger blueprints without auth

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4. Missing or Weak Security Headers (High)

Scan HTTP responses for these headers. All must be present in production.

| Header | Required Value / Pattern | |--------|--------------------------| | Strict-Transport-Security | max-age=31536000; includeSubDomains | | X-Content-Type-Options | nosniff | | X-Frame-Options | DENY or SAMEORIGIN | | Content-Security-Policy | Domain-specific; at minimum block unsafe-inline | | Referrer-Policy | strict-origin-when-cross-origin | | Permissions-Policy | Restrict camera, mic, geolocation as appropriate |

Flask — use flask-talisman:

from flask_talisman import Talisman
Talisman(app, force_https=True, content_security_policy={
    "default-src": "'self'",
    "script-src": ["'self'", "cdn.example.com"],
})

FastAPI — middleware approach:

from starlette.middleware.httpsredirect import HTTPSRedirectMiddleware
from starlette.middleware import Middleware
from secure import SecureHeaders  # 'secure' package

secure_headers = SecureHeaders()

@app.middleware("http")
async def set_secure_headers(request, call_next):
    response = await call_next(request)
    secure_headers.starlette(response)
    return response

Key CWEs: CWE-16 (Configuration), CWE-1021 (Improper Frame Restrictions)

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5. Insecure Cookie Flags (High)

Flask session cookie:

# BAD defaults — cookies sent over HTTP, accessible by JS
app.config["SESSION_COOKIE_SECURE"] = False
app.config["SESSION_COOKIE_HTTPONLY"] = False

# GOOD
app.config.update(
    SESSION_COOKIE_SECURE=True,       # HTTPS only
    SESSION_COOKIE_HTTPONLY=True,     # No JS access
    SESSION_COOKIE_SAMESITE="Lax",   # CSRF protection
    SESSION_COOKIE_NAME="__Host-session",  # __Host- prefix enforces additional constraints
    PERMANENT_SESSION_LIFETIME=3600,  # 1-hour expiry
)

FastAPI — when setting cookies manually:

response.set_cookie(
    key="session",
    value=token,
    httponly=True,
    secure=True,
    samesite="lax",
    max_age=3600,
)

Key CWEs: CWE-614 (Sensitive Cookie Without Secure), CWE-1004 (Sensitive Cookie Without HttpOnly)

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6. XML External Entity (XXE) Processing (High)

Flag any XML parsing that doesn't explicitly disable external entities:

# BAD — lxml with default parser
from lxml import etree
tree = etree.parse(xml_input)  # vulnerable

# BAD — stdlib xml.etree (not vulnerable to XXE by default, but flag for review)
import xml.etree.ElementTree as ET
ET.fromstring(user_input)  # safe in CPython, but document why

# GOOD — lxml with entity expansion disabled
parser = etree.XMLParser(
    resolve_entities=False,
    no_network=True,
    load_dtd=False,
)
tree = etree.parse(xml_input, parser)

# GOOD — use defusedxml for untrusted input
import defusedxml.ElementTree as ET
tree = ET.fromstring(user_input)

• Bandit rule: B405, B408, B410 (xml_* rules)
• Key CWE: CWE-611 (XXE)

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7. Unnecessary Features / Attack Surface (Medium)

Check for services, routes, or middleware that shouldn't exist in production:

• Werkzeug profiler — remove ProfilerMiddleware in production
• Flask shell — disable or restrict access to /console routes
• Admin interfaces — flask-admin, sqladmin must be behind auth + IP restriction
• Debug endpoints — flag any route returning sys.environ, stack traces, or internal state
• Unused middleware — audit app.wsgi_app chain in Flask; app.middleware_stack in FastAPI

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8. Cloud / Infrastructure Misconfiguration (Medium)

While code-level scanning can't catch all infra misconfig, flag these patterns:

• S3 bucket names in code — check for public ACL patterns or missing bucket policies
• Database connection strings — flag if connection uses sslmode=disable
• CORS too permissive:

# BAD — FastAPI
from fastapi.middleware.cors import CORSMiddleware
app.add_middleware(CORSMiddleware, allow_origins=["*"], allow_credentials=True)
# allow_origins=["*"] + allow_credentials=True is rejected by browsers but signals intent error

# GOOD
app.add_middleware(CORSMiddleware,
    allow_origins=["https://app.example.com"],
    allow_credentials=True,
    allow_methods=["GET", "POST"],
    allow_headers=["Authorization", "Content-Type"],
)

# BAD — Flask
from flask_cors import CORS
CORS(app, origins="*")

# GOOD
CORS(app, origins=["https://app.example.com"], supports_credentials=True)

Key CWE: CWE-16 (Configuration)

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Tooling

Bandit (SAST) — Primary Tool

pip install bandit
bandit -r ./app -f json -o bandit-report.json

# Focus on misconfiguration-relevant rules:
bandit -r ./app -t B105,B106,B107,B201,B405,B408,B410

Key Bandit rules for A02: | Rule | Description | |------|-------------| | B105 | Hardcoded password string | | B106 | Hardcoded password funcarg | | B107 | Hardcoded password default | | B201 | flask_debug_true | | B405 | import xml.etree — recommend defusedxml | | B408 | import xml.minidom — recommend defusedxml | | B410 | import lxml — flag for XXE review |

OWASP ZAP (DAST) — Header & Config Validation

# Docker quick scan — checks headers, misconfigured endpoints, debug info leaks
docker run -t owasp/zap2docker-stable zap-baseline.py \
  -t https://your-app.example.com \
  -r zap-report.html

ZAP automatically tests for: missing security headers, exposed stack traces, directory listing, debug endpoints, insecure cookies.

python-dotenv + pydantic-settings (Prevention)

pip install python-dotenv pydantic-settings

from pydantic_settings import BaseSettings

class Settings(BaseSettings):
    secret_key: str              # required — fails fast if missing
    database_url: str
    debug: bool = False          # safe default
    env: str = "production"

    class Config:
        env_file = ".env"        # loaded only in dev; never committed

settings = Settings()

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Key CWEs Summary

| CWE | Description | Severity | |-----|-------------|----------| | CWE-16 | Configuration (catch-all) | High | | CWE-489 | Active Debug Code | Critical | | CWE-526 | Sensitive Info in Environment Variables | High | | CWE-321 | Hard-coded Cryptographic Key | Critical | | CWE-611 | XML External Entity (XXE) | High | | CWE-614 | Sensitive Cookie Without Secure Attribute | High | | CWE-1004 | Sensitive Cookie Without HttpOnly Attribute | High |

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Quick Audit Command

Run this one-liner for a fast A02 surface scan on any Python project:

bandit -r . -t B105,B106,B107,B201,B405,B408,B410 --severity-level medium \
  && grep -rn "debug=True\|FLASK_DEBUG=1\|allow_origins=\[.\"\*\"\]\|verify=False" . \
  && echo "Manual checks needed: /docs exposure, cookie flags, security headers"

Source & license

This open-source skill is cataloged on AgentStack and links to its original source — we do not rehost the code.

• Author: scholarly360
• Source: scholarly360/owasp-top10-web-skills
• License: MIT

Install and usage instructions live in the source repository linked above.