Week 4 Scripting Exercise: Analyze HTTP Response Headers

Week 4 Scripting Exercise: Build a Web Reconnaissance Report Generator

Time: 2-4 hours

Type: Free-response scripting project

Skills: HTTP Protocol, Python requests/parsing, Security Headers, Cookie Analysis

🎯 The Challenge

From Grace Nolan’s Security Engineering Interview Notes:

"Web scrapers - Write a script to scrape information from a website."

Your task: Build a Python script that performs passive reconnaissance on a target URL and generates a security-focused report.

This is the discovery phase of security assessments - understanding what you’re looking at before testing anything.

⭐ This exercise is part of my open-source Security Engineering curriculum.

If you find this helpful, **[star the repo on GitHub](https://git…

Week 4 Scripting Exercise: Build a Web Reconnaissance Report Generator

Time: 2-4 hours

Type: Free-response scripting project

Skills: HTTP Protocol, Python requests/parsing, Security Headers, Cookie Analysis

🎯 The Challenge

From Grace Nolan’s Security Engineering Interview Notes:

"Web scrapers - Write a script to scrape information from a website."

Your task: Build a Python script that performs passive reconnaissance on a target URL and generates a security-focused report.

This is the discovery phase of security assessments - understanding what you’re looking at before testing anything.

⭐ This exercise is part of my open-source Security Engineering curriculum.

If you find this helpful, star the repo on GitHub to support the project and get notified when new exercises drop!

Background Reading

Before you start coding, review these concepts:

From Grace Nolan’s Notes (Networking Section)

HTTP Response Headers contain:

Status codes (1xx informational, 2xx success, 3xx redirect, 4xx client error, 5xx server error)
Content type and encoding
Server identification

Cookies:

HttpOnly - cannot be accessed by JavaScript (XSS mitigation)
Secure - only sent over HTTPS
SameSite - CSRF protection (Strict, Lax, None)

From Hacking APIs, Chapter 6: Discovery (pp. 125-147)

The passive reconnaissance process has three phases:

Cast a Wide Net - Gather general information about the target
Adapt and Focus - Refine based on findings
Document the Attack Surface - Record everything useful

Key quote:

"Taking notes is crucial to performing an effective attack. Document and take screen captures of all interesting findings."

From Full Stack Python Security

Chapter 7 (pp. 86-89) - HTTP Cookies:

Cookies are sent via Set-Cookie response header
Session IDs are commonly stored in cookies
The Secure directive prevents transmission over HTTP
The Domain directive controls which domains receive the cookie

Chapter 14 (pp. 222-224) - Security Response Headers:

HttpOnly hides cookies from JavaScript (document.cookie)
X-Content-Type-Options: nosniff prevents MIME sniffing attacks
Missing security headers are common findings in assessments

From API Security in Action, Chapter 5 (pp. 151-153)

CORS Headers:

Access-Control-Allow-Origin - Which origins can access resources
Access-Control-Allow-Credentials - Whether cookies are sent
Wildcard (*) with credentials is a security misconfiguration

Your Assignment

Build a Python script called web_recon.py that:

Takes a URL as input (command line argument or user prompt)
Makes an HTTP request to the target
Extracts and displays the following information:

Part 1: Basic Response Information

Extract and display:

═══ RESPONSE STATUS ═══
Status Code: 200
Status Message: OK
HTTP Version: HTTP/1.1
Response Time: 0.234 seconds

Why this matters: Status codes reveal application behavior. A 403 vs 404 can indicate whether a resource exists.

Part 2: Server Information (Technology Fingerprinting)

Look for headers that reveal server technology and display their values:

═══ SERVER INFORMATION ═══
Server: nginx/1.18.0
X-Powered-By: PHP/7.4.3
X-AspNet-Version: (not present)
X-Generator: WordPress 5.8
X-Drupal-Cache: (not present)

Headers to check:

Server
X-Powered-By
X-AspNet-Version
X-Generator
X-Drupal-Cache
X-Varnish

Why this matters: These headers reveal what software is running. Security analysts can then search for CVEs affecting those versions.

Note: Just report if these headers exist and show their values. Let the human analyst assess the risk - that’s what real recon tools do.

Part 3: Security Headers Analysis

Check for presence/absence of security headers:

═══ SECURITY HEADERS ═══
X-Frame-Options: DENY ✓
X-Content-Type-Options: nosniff ✓
X-XSS-Protection: (not present) ⚠️
Strict-Transport-Security: max-age=31536000; includeSubDomains ✓
Content-Security-Policy: (not present) ⚠️
Referrer-Policy: strict-origin-when-cross-origin ✓
Permissions-Policy: (not present) ⚠️

Security Header Score: 4/7

Headers to check:

Header	Purpose	Risk if Missing
`X-Frame-Options`	Prevents clickjacking	Clickjacking attacks
`X-Content-Type-Options`	Prevents MIME sniffing	Content type attacks
`X-XSS-Protection`	Browser XSS filter	XSS (legacy browsers)
`Strict-Transport-Security`	Enforces HTTPS	Downgrade attacks
`Content-Security-Policy`	Controls resource loading	XSS, injection
`Referrer-Policy`	Controls referrer info	Information leakage
`Permissions-Policy`	Controls browser features	Privacy issues

Part 4: Cookie Analysis

Parse all Set-Cookie headers and analyze security attributes:

═══ COOKIES ═══
Cookie 1: session
Value: abc123...def (truncated)
HttpOnly: ✓ Yes
Secure: ✓ Yes
SameSite: Strict
Domain: .example.com
Path: /
Max-Age: 86400 (1 day)

Cookie 2: tracking_id
Value: xyz789
HttpOnly: ✗ No ⚠️
Secure: ✗ No ⚠️
SameSite: (not set) ⚠️

⚠️  FINDING: Cookie 'tracking_id' missing HttpOnly - vulnerable to XSS theft
⚠️  FINDING: Cookie 'tracking_id' missing Secure - sent over HTTP
⚠️  FINDING: Cookie 'tracking_id' missing SameSite - CSRF risk

Cookie attributes to extract:

Name and value (truncate long values)
HttpOnly flag (boolean)
Secure flag (boolean)
SameSite value (Strict/Lax/None or not set)
Domain scope
Path scope
Max-Age or Expires

Part 5: CORS Configuration

Check for CORS headers and potential misconfigurations:

═══ CORS CONFIGURATION ═══
Access-Control-Allow-Origin: *
Access-Control-Allow-Credentials: true
Access-Control-Allow-Methods: GET, POST, DELETE
Access-Control-Allow-Headers: Content-Type, Authorization

🚨 CRITICAL: Wildcard origin (*) with Allow-Credentials is a security vulnerability!

CORS security rules:

* origin with credentials: true = CRITICAL vulnerability
Overly permissive methods (DELETE, PUT) = note for testing

Part 6: Additional Reconnaissance

Extract any other useful information:

═══ ADDITIONAL INFORMATION ═══
Content-Type: text/html; charset=utf-8
Content-Length: 45678
Content-Encoding: gzip
Cache-Control: no-cache, no-store
ETag: "abc123"

Interesting Headers Found:
- X-Request-ID: req-12345 (useful for log correlation)
- X-RateLimit-Remaining: 99 (rate limiting detected)
- Via: 1.1 proxy.example.com (proxy detected)

Part 7: Generate Summary Report

End with an executive summary:

═══════════════════════════════════════════════════════════════
RECONNAISSANCE SUMMARY
═══════════════════════════════════════════════════════════════
Target: https://example.com
Scan Time: 2026-01-03 10:30:00 UTC

FINDINGS:
🚨 CRITICAL (1):
- CORS misconfiguration: wildcard with credentials

⚠️  MEDIUM (3):
- Missing Content-Security-Policy header
- Cookie 'tracking_id' missing HttpOnly
- Missing X-Frame-Options header

ℹ️  INFO (4):
- Server: nginx/1.18.0
- X-Powered-By: PHP/7.4.3
- Rate limiting detected
- Proxy detected in request path

SECURITY HEADER SCORE: 4/7 (57%)
COOKIE SECURITY SCORE: 1/2 cookies properly secured (50%)

RECOMMENDED NEXT STEPS:
1. Search for CVEs: nginx 1.18.0, PHP 7.4.3
2. Test for clickjacking (X-Frame-Options present)
3. Test XSS vectors (no CSP)
4. Test CSRF on state-changing operations
═══════════════════════════════════════════════════════════════

Example Output

When run against a target, your script should produce output similar to:

$ python3 web_recon.py https://example.com

[*] Starting reconnaissance on: https://example.com
[*] Time: 2026-01-03T10:30:00Z

═══ RESPONSE STATUS ═══
Status Code: 200
Status Message: OK
Response Time: 0.342s

═══ SERVER INFORMATION ═══
Server: ECS (dcb/7F84)
X-Powered-By: (not present)

═══ SECURITY HEADERS ═══
X-Frame-Options: (not present) ⚠️
X-Content-Type-Options: (not present) ⚠️
Strict-Transport-Security: (not present) ⚠️
Content-Security-Policy: (not present) ⚠️

Security Header Score: 0/7

═══ COOKIES ═══
No cookies set.

═══ CORS CONFIGURATION ═══
No CORS headers present.

═══ RECONNAISSANCE SUMMARY ═══
Target: https://example.com
Findings: 4 missing security headers
Recommendation: Review security header configuration

Scoring Rules

Cookie Security Score

Each cookie is scored out of 3 points:

Attribute	Points	Rule
`HttpOnly`	1	Present = 1 point, Missing = 0
`Secure`	1	Present = 1 point, Missing = 0
`SameSite`	1	`Strict` or `Lax` = 1 point, `None` or missing = 0

Cookie Security Score = (Total points earned) / (Total possible points) × 100%

Example:

Cookie 1: session    → HttpOnly ✓, Secure ✓, SameSite=Strict ✓  → 3/3
Cookie 2: tracking   → HttpOnly ✗, Secure ✓, SameSite ✗         → 1/3
Cookie 3: preference → HttpOnly ✗, Secure ✗, SameSite=Lax ✓     → 1/3

Total: 5/9 = 55.6%
Cookie Security Score: 55.6%

Security Header Score

Score out of 7 points (1 point per header present):

Header	Points
`X-Frame-Options`	1
`X-Content-Type-Options`	1
`X-XSS-Protection`	1
`Strict-Transport-Security`	1
`Content-Security-Policy`	1
`Referrer-Policy`	1
`Permissions-Policy`	1

Security Header Score = Headers present / 7 × 100%

Finding Severity Levels

Use these rules to categorize each finding:

🚨 CRITICAL

Finding	Condition
CORS misconfiguration	`Access-Control-Allow-Origin: *` AND `Access-Control-Allow-Credentials: true` both present

⚠️ MEDIUM

Finding	Condition
Missing Content-Security-Policy	`Content-Security-Policy` header not present
Missing HSTS	`Strict-Transport-Security` header not present (HTTPS sites only)
Missing X-Frame-Options	`X-Frame-Options` header not present
Missing X-Content-Type-Options	`X-Content-Type-Options` header not present
Cookie missing HttpOnly	Any cookie where `HttpOnly` is not set
Cookie missing Secure	Any cookie where `Secure` is not set (HTTPS sites only)
Cookie missing SameSite	Any cookie without `SameSite` attribute or with `SameSite=None`

ℹ️ INFO

Finding	Condition
Server header present	`Server` header exists - display its value
X-Powered-By present	`X-Powered-By` header exists - display its value
Technology fingerprint	`X-Generator`, `X-AspNet-Version`, `X-Drupal-Cache`, etc. present
Rate limiting detected	`X-RateLimit-` or `RateLimit-` headers present
Proxy detected	`Via` or `X-Forwarded-*` headers present
CDN detected	`X-Cache`, `CF-Ray`, `X-Served-By`, or similar headers present
Missing X-XSS-Protection	`X-XSS-Protection` header not present (deprecated header)
Missing Permissions-Policy	`Permissions-Policy` header not present
Missing Referrer-Policy	`Referrer-Policy` header not present

Why is server version INFO and not HIGH?

Detecting version numbers like nginx/1.18.0 vs nginx requires regex pattern matching. We’re keeping this exercise focused on HTTP fundamentals and string parsing. Just report what you find - security analysts know to look up CVEs for any versions shown.

Example Severity Classification

Target: https://example.com

🚨 CRITICAL (0):
(none)

⚠️  MEDIUM (5):
- Missing Content-Security-Policy header
- Missing Strict-Transport-Security header
- Cookie 'tracking' missing HttpOnly
- Cookie 'tracking' missing SameSite attribute
- Missing X-Frame-Options header

ℹ️  INFO (4):
- Server: nginx/1.18.0
- X-Powered-By: PHP/7.4.3
- CDN detected: Cloudflare (CF-Ray header)
- Missing Permissions-Policy header

Grading Criteria

Your script will be evaluated on:

Criteria	Points
Successfully fetches URL and handles errors	10
Extracts status code, message, response time	10
Reports server information headers	15
Checks all 7 security headers	15
Parses cookies with all attributes	20
Detects CORS misconfigurations	15
Generates clear, readable summary	10
Code quality and error handling	5
Total	100

Bonus Challenges

Once your basic script works:

Add robots.txt fetching - Check for /robots.txt and list disallowed paths
Check multiple URLs - Accept a file of URLs to scan
Export to JSON - Save findings in structured format
Compare to baseline - Load a "known good" config and diff against it

Submission

When complete, your deliverables should include:

web_recon.py - Your Python script
Sample output from running against 2-3 real websites
Brief notes on any interesting findings

🔍 Reference Solution

Stuck? Want to compare your approach?

View the reference solution on GitHub →

⚠️ Try it yourself first! The learning happens in the struggle. Only check the solution after you’ve attempted the exercise or if you’re completely stuck.

The reference solution scores 91/100 and demonstrates:

File-based URL input with comment skipping
Complete security header analysis (7/7 headers)
Cookie parsing with HttpOnly, Secure, and SameSite extraction
CORS misconfiguration detection
Severity-categorized findings (CRITICAL/MEDIUM/INFO)
Security Header Score and Cookie Security Score calculations

Usage

# Scan multiple URLs from a file
python3 web_recon.py practice_urls.txt

# Scan a single URL directly
python3 web_recon.py https://example.com

File format (practice_urls.txt):

# Lines starting with # are comments
https://github.com
https://example.com
https://stripe.com

Note: The reference solution accepts a file of URLs. You can implement yours to accept either a file or a single URL directly.

Resources

Primary Sources

Grace Nolan’s Notes: https://github.com/gracenolan/Notes
Hacking APIs (Corey Ball) - Chapter 6: Discovery
Full Stack Python Security - Chapters 7 and 14
API Security in Action - Chapter 5

Reference Documentation

Tools to Compare Against

SecurityHeaders.com - Online header scanner
Mozilla Observatory - Comprehensive scanner

Why This Matters

This exercise builds skills directly applicable to:

Bug Bounty Hunting: Reconnaissance is the first step in finding vulnerabilities
Penetration Testing: Discovery phase of every engagement
Security Auditing: Automated header/cookie policy checking
Security Engineering Interviews: Grace Nolan specifically lists this as a coding challenge

As noted in Hacking APIs:

"Taking notes is crucial to performing an effective attack. Document and take screen captures of all interesting findings."

Your script automates this documentation process.

🌟 Found This Helpful?

This exercise is part of my 48-Week Security Engineering Curriculum - a complete roadmap from networking fundamentals to landing a Security Engineering role.

⭐ Star the repo on GitHub to:

Support the project
Get notified when new exercises drop
Help others discover these resources

The curriculum includes:

📚 Weekly study guides with page-by-page reading assignments
🛠️ Hands-on scripting exercises (like this one!)
🎯 PortSwigger lab progressions
📝 Interview prep from Grace Nolan’s notes

Check it out →

Share Your Results!

Built your recon tool? I’d love to see it!

Compare with the reference solution - See how your approach differs
Tweet your output with #SecurityEngineering and tag me
Open a PR to add your solution to the community solutions folder
Post interesting findings (from authorized testing only!) in the discussions

Week 4 of the 48-Week Security Engineering Curriculum: Linux Security + Python Files

Week 4 Scripting Exercise: Build a Web Reconnaissance Report Generator

🎯 The Challenge

Week 4 Scripting Exercise: Build a Web Reconnaissance Report Generator

🎯 The Challenge

Background Reading

From Grace Nolan’s Notes (Networking Section)

From Hacking APIs, Chapter 6: Discovery (pp. 125-147)

From Full Stack Python Security

From API Security in Action, Chapter 5 (pp. 151-153)

Your Assignment

Part 1: Basic Response Information

Part 2: Server Information (Technology Fingerprinting)

Part 3: Security Headers Analysis

Part 4: Cookie Analysis

Part 5: CORS Configuration

Part 6: Additional Reconnaissance

Part 7: Generate Summary Report

Example Output

Scoring Rules

Cookie Security Score

Security Header Score

Finding Severity Levels

🚨 CRITICAL

⚠️ MEDIUM

ℹ️ INFO

Example Severity Classification

Grading Criteria

Bonus Challenges

Submission

🔍 Reference Solution

Usage

Resources

Primary Sources

Reference Documentation

Tools to Compare Against

Why This Matters

🌟 Found This Helpful?

Share Your Results!

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