RoadMap-180: Cybersecurity & Advanced

Python OOP
16/05/2025 start

� Stage 1 (Startup) - Focus Areas:

� Cybersecurity: Ethical Hacking Basics, Linux Commands, Burp Suite, Web
Attacks (SQLi, XSS) � Python: Python Fundamentals, OOP Basics, Data
Structures, File Handling

� Day 1-10: Cybersecurity + Python Basics

� Day 1
• Cybersecurity: Revise Networking (TCP/IP, OSI Model, Subnetting
Basics)
• Cybersecurity Practice: Set up a small virtual network in Virtual-
Box/VMware and analyze traffic with Wireshark
• Python: Python Setup, Variables, Data Types, Basic Operators
• Python Practice: Create a simple network scanner that pings IP ad-
dresses in a given range

� Day 2
• Cybersecurity: Linux Command Line (Basic Commands, File System,
Users & Permissions)
• Cybersecurity Practice: Complete 5 Linux challenges on TryHackMe
or OverTheWire Bandit
• Python: Control Flow (if-elif-else, loops, list comprehensions)
• Python Practice: Write a script to check file permissions in a directory
and identify insecure settings

� Day 3
• Cybersecurity: Linux Scripting (Bash Basics) + Networking Tools
(Ping, Traceroute, Netstat)
• Cybersecurity Practice: Write a bash script to automate system recon-
naissance
• Python: Functions, Lambda Expressions, Map/Filter/Reduce
• Python Practice: Create a script that analyzes network connections
using Python’s socket module

� Day 4
• Cybersecurity: Web Attack Basics (HTTP Basics, Burp Suite Setup)

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 • Cybersecurity Practice: Set up Burp Suite and intercept/modify sim-
ple HTTP requests
• Python: OOP Basics (Classes, Objects, Attributes, Methods)
• Python Practice: Create a simple “WebRequest” class with methods to
perform GET/POST requests

� Day 5
• Cybersecurity: SQL Injection Basics (Manual SQLi, Login Bypass)
• Cybersecurity Practice: Practice SQLi on a vulnerable lab environ-
ment (DVWA or SQLi-labs)
• Python: Inheritance and Polymorphism
• Python Practice: Extend your WebRequest class with specialized
classes for different API interactions

� Day 6
• Cybersecurity: Cross-Site Scripting (XSS) + Burp Suite Practice
• Cybersecurity Practice: Find and exploit 3 XSS vulnerabilities in a
practice environment
• Python: Encapsulation, Properties, and Access Modifiers
• Python Practice: Create a secure data container class with proper en-
capsulation for sensitive information

� Day 7
• Cybersecurity: File Inclusion Attacks (LFI, RFI)
• Cybersecurity Practice: Set up a vulnerable PHP application and ex-
ploit LFI vulnerabilities
• Python: Error Handling (Try/Except), Context Managers
• Python Practice: Create a file analyzer with proper error handling that
checks for potentially malicious content

� Day 8
• Cybersecurity: Brute Force Attacks (Hydra, John the Ripper Basics)
• Cybersecurity Practice: Crack a password hash using John the Ripper
• Python: Advanced Data Structures (Sets, Dictionaries, Collections)
• Python Practice: Build a password strength checker using dictionaries
and sets

� Day 9
• Cybersecurity: Password Cracking (Hashcat Basics)
• Cybersecurity Practice: Use Hashcat to crack 3 different hash types
• Python: File I/O, Working with CSV and JSON

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 • Python Practice: Create a tool that parses log files for suspicious activ-
ities and generates a report

� Day 10 � Review Day

• Cybersecurity: Practice Linux, SQLi, XSS, Burp Suite
• Cybersecurity Practice: Complete a basic CTF challenge incorporating
multiple concepts
• Python: Solve Python challenges, Build a mini project (Security Scanner)
• Python Practice: Combine all week’s concepts into a tool that performs
basic security checks on a target

� Stage 2 (Intermediate) - Focus Areas:

� Cybersecurity: Vulnerability Assessment, Web Pentesting (Advanced SQLi,
XSS, CSRF, SSRF), Exploit Development Basics � Python: Advanced OOP,
Design Patterns, Decorators, Generators, Metaclasses

� Day 11-20: Web Security & Python Advanced OOP

� Day 11
• Cybersecurity: Advanced SQL Injection (Boolean, Time-Based, Union-
Based)
• Cybersecurity Practice: Exploit advanced SQLi vulnerabilities in
PortSwigger Web Security Academy
• Python: Class Methods, Static Methods, Abstract Classes
• Python Practice: Create a vulnerability scanner framework with ab-
stract base classes and concrete implementations

� Day 12
• Cybersecurity: Cross-Site Scripting (Stored, DOM-Based) + Prevention
• Cybersecurity Practice: Find and exploit 3 DOM-based XSS vulnera-
bilities
• Python: Magic Methods and Operator Overloading
• Python Practice: Create a custom data structure class with magic meth-
ods for security analysis

� Day 13
• Cybersecurity: CSRF (Cross-Site Request Forgery) + Exploitation
• Cybersecurity Practice: Create a CSRF exploit for a vulnerable appli-
cation
• Python: Advanced Inheritance (Multiple, Multilevel, Method Resolution
Order)
• Python Practice: Implement a class hierarchy for different types of web
vulnerabilities

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� Day 14
• Cybersecurity: Open Redirection & SSRF (Server-Side Request
Forgery)
• Cybersecurity Practice: Test for and exploit SSRF in a lab environ-
ment
• Python: Design Patterns I (Singleton, Factory, Observer)
• Python Practice: Implement a logging system using the Observer pat-
tern

� Day 15
• Cybersecurity: Directory Traversal & File Upload Vulnerabilities
• Cybersecurity Practice: Exploit file upload vulnerabilities to get re-
mote code execution
• Python: Design Patterns II (Strategy, Decorator, Adapter)
• Python Practice: Create a modular payload generator using design
patterns

� Day 16
• Cybersecurity: Subdomain Enumeration (Sublist3r, Amass)
• Cybersecurity Practice: Find subdomains for a target website (with
permission)
• Python: Decorators and Closures
• Python Practice: Create a decorator for timing function execution and
logging results

� Day 17
• Cybersecurity: Web Pentesting Practice (DVWA, Juice Shop)
• Cybersecurity Practice: Solve 5 different challenge types in OWASP
Juice Shop
• Python: Generators and Iterators
• Python Practice: Create a network packet generator using Python gen-
erators

� Day 18
• Cybersecurity: Burp Suite Advanced Usage (Intruder, Repeater, Col-
laborator)
• Cybersecurity Practice: Use Burp Intruder to automate parameter
testing
• Python: Metaclasses and Class Customization
• Python Practice: Create a secure object factory using metaclasses

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� Day 19
• Cybersecurity: Introduction to Exploit Development (Buffer Overflow
Basics)
• Cybersecurity Practice: Execute a simple buffer overflow on a vulner-
able program
• Python: Context Managers and the with Statement
• Python Practice: Create custom context managers for secure file han-
dling and network connections

� Day 20 � Review Day

• Cybersecurity: Hands-on Labs (Hack The Box, TryHackMe Challenges)
• Cybersecurity Practice: Complete a medium difficulty box on Hack-
TheBox or TryHackMe
• Python: Mini Project (Vulnerability Scanner)
• Python Practice: Enhance your scanner with advanced OOP techniques
and design patterns

� Day 21-30: Exploitation & Python Frameworks

� Day 21
• Cybersecurity: Reverse Shells & Payloads (Netcat, MSFVenom)
• Cybersecurity Practice: Generate and test various payload types with
MSFVenom
• Python: Introduction to Flask Framework
• Python Practice: Create a basic API with Flask for security tool man-
agement

� Day 22
• Cybersecurity: Privilege Escalation (Linux, Windows)
• Cybersecurity Practice: Identify and exploit sudo misconfigurations
on Linux
• Python: Flask Routing and Templates
• Python Practice: Build a web dashboard to display vulnerability scan
results

� Day 23
• Cybersecurity: WebShells & Backdoors (PHP, ASPX Shells)
• Cybersecurity Practice: Create and analyze a custom web shell
• Python: Database Integration with SQLAlchemy
• Python Practice: Create a vulnerability database with SQLAlchemy
ORM

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� Day 24
• Cybersecurity: Active Directory Enumeration & Attacks (BloodHound,
Kerberoasting)
• Cybersecurity Practice: Set up a small AD environment and enumer-
ate with BloodHound
• Python: Concurrent Programming (Threading, Multiprocessing)
• Python Practice: Create a multi-threaded port scanner

� Day 25
• Cybersecurity: Exploit Writing Basics (Python Scripting for Exploits)
• Cybersecurity Practice: Modify an existing exploit to work for a spe-
cific target
• Python: Asyncio and Asynchronous Programming
• Python Practice: Create an asynchronous web crawler for reconnais-
sance

� Day 26
• Cybersecurity: Exploiting Misconfigurations (S3 Buckets, Docker, Ku-
bernetes)
• Cybersecurity Practice: Identify misconfigurations in cloud services
(using safe/legal methods)
• Python: Working with APIs (REST, GraphQL)
• Python Practice: Create a tool to check for misconfigured cloud services
via APIs

� Day 27
• Cybersecurity: Reverse Engineering Basics (Ghidra, IDA Pro)
• Cybersecurity Practice: Analyze a simple binary in Ghidra and iden-
tify vulnerabilities
• Python: Advanced Memory Management and Optimization
• Python Practice: Create a memory-efficient log analyzer for large files

� Day 28
• Cybersecurity: Fuzzing & Exploiting Web Apps (ffuf, wfuzz)
• Cybersecurity Practice: Use fuzzing tools to find hidden endpoints and
vulnerabilities
• Python: Unit Testing and Test-Driven Development
• Python Practice: Write unit tests for your security tools

� Day 29
• Cybersecurity: Exploiting CTF Challenges (HackTheBox, TryHackMe)

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 • Cybersecurity Practice: Solve a web exploitation challenge on Hack-
TheBox
• Python: Packaging and Distribution
• Python Practice: Package one of your security tools for distribution

� Day 30 � Review Day

• Cybersecurity: CTF Challenge on TryHackMe / HackTheBox
• Cybersecurity Practice: Attempt a medium-hard CTF and document
your approach
• Python: Full-Stack Mini Project (Security Tool Suite)
• Python Practice: Integrate multiple tools into a cohesive security toolkit

� Stage 3 (Advanced) - Focus Areas

� Cybersecurity: Advanced Pentesting (Active Directory, Privilege Escala-
tion, Exploit Development) � Python: Advanced Frameworks, Data Analysis,
Machine Learning for Security

� Day 31-40: Advanced Web Hacking + Python for Security

� Day 31
• Cybersecurity: Advanced Burp Suite (Intruder, Collaborator, Exten-
sions)
• Cybersecurity Practice: Create a custom Burp extension for a specific
testing scenario
• Python: Advanced Data Analysis with Pandas
• Python Practice: Analyze vulnerability scan data with Pandas

� Day 32
• Cybersecurity: Insecure Deserialization & NoSQL Injection
• Cybersecurity Practice: Exploit a deserialisation vulnerability in a lab
environment
• Python: NumPy and Scientific Computing
• Python Practice: Create a network traffic analyzer using NumPy

� Day 33
• Cybersecurity: SSRF & Exploiting Cloud Services
• Cybersecurity Practice: Chain SSRF with other vulnerabilities in a
lab environment
• Python: Data Visualization (Matplotlib, Seaborn)
• Python Practice: Create visualizations for security posture assessment

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� Day 34
• Cybersecurity: Automating Web Attacks (Python + Requests + Beau-
tifulSoup)
• Cybersecurity Practice: Create a script to automate a multi-step web
attack
• Python: Web Scraping and OSINT Tools
• Python Practice: Build an OSINT reconnaissance tool

� Day 35
• Cybersecurity: Reverse Engineering with Ghidra + Malware Analysis
Basics
• Cybersecurity Practice: Reverse engineer a simple malware sample in
a safe environment
• Python: Introduction to Machine Learning with scikit-learn
• Python Practice: Create a basic malware classifier

� Day 36
• Cybersecurity: Windows Exploitation (DLL Hijacking, Registry Persis-
tence)
• Cybersecurity Practice: Set up a lab and perform DLL hijacking
• Python: Natural Language Processing Basics
• Python Practice: Build a log analyzer with NLP capabilities

� Day 37
• Cybersecurity: Advanced Privilege Escalation (Windows & Linux)
• Cybersecurity Practice: Create a privilege escalation cheatsheet and
test techniques
• Python: Custom Network Protocol Analysis
• Python Practice: Create a custom protocol analyzer using Scapy

� Day 38
• Cybersecurity: Active Directory Attacks (NTLM Relay, Pass-the-Hash)
• Cybersecurity Practice: Set up and execute an NTLM relay attack in
a lab environment
• Python: Building Custom Security Tools
• Python Practice: Create a tool to detect and simulate credential-based
attacks

� Day 39
• Cybersecurity: Hands-on Lab (TryHackMe / HackTheBox Active Di-
rectory Challenges)

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 • Cybersecurity Practice: Complete an Active Directory focused chal-
lenge
• Python: Advanced GUI Development (PyQt, Tkinter)
• Python Practice: Create a GUI for one of your security tools

� Day 40 � Review Day

• Cybersecurity: AD & Web Exploits Revision
• Cybersecurity Practice: Chain multiple attack techniques in a compre-
hensive lab
• Python: Full-Stack Project Review
• Python Practice: Integrate data analysis capabilities into your security
toolkit

� Day 41-50: Exploit Development + Advanced Python Applications

� Day 41
• Cybersecurity: Buffer Overflow (Windows) + Exploit Development
• Cybersecurity Practice: Develop a full exploit for a buffer overflow
vulnerability
• Python: Advanced Network Programming
• Python Practice: Create a custom network protocol fuzzer

� Day 42
• Cybersecurity: Format String Vulnerabilities & Exploitation
• Cybersecurity Practice: Exploit format string vulnerabilities in a con-
trolled environment
• Python: Memory Forensics with Volatility
• Python Practice: Write a Volatility plugin for malware detection

� Day 43
• Cybersecurity: Shellcode Injection & Writing Custom Exploits
• Cybersecurity Practice: Create and test shellcode for a specific vulner-
ability
• Python: Building a Custom Command & Control Framework
• Python Practice: Create a basic command and control server and client

� Day 44
• Cybersecurity: Malware Development (Packing, Obfuscation)
• Cybersecurity Practice: Analyze and deobfuscate a packed sample
• Python: Code Obfuscation and Deobfuscation
• Python Practice: Create tools to obfuscate and deobfuscate Python
code

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� Day 45
• Cybersecurity: Reverse Shell Payload Development
• Cybersecurity Practice: Create custom reverse shells that evade com-
mon detection
• Python: Advanced Cryptography
• Python Practice: Implement custom encryption/decryption tools

� Day 46
• Cybersecurity: Hands-on Buffer Overflow Exploits (WinDbg, Immunity
Debugger)
• Cybersecurity Practice: Debug and exploit a buffer overflow step-by-
step
• Python: Binary Analysis with Python
• Python Practice: Create a binary analysis tool for vulnerability detec-
tion

� Day 47
• Cybersecurity: Advanced Active Directory Exploits (Golden Ticket, Sil-
ver Ticket)
• Cybersecurity Practice: Create and use Kerberos tickets in a lab envi-
ronment
• Python: Machine Learning for Anomaly Detection
• Python Practice: Build a behavior-based anomaly detection system

� Day 48
• Cybersecurity: Web Application Firewalls (WAF) Bypass Techniques
• Cybersecurity Practice: Test and document 5 different WAF bypass
techniques
• Python: Advanced Web Application Testing
• Python Practice: Create an automated web vulnerability scanner

� Day 49
• Cybersecurity: Final Web Hacking Challenges (Bug Bounty Platforms)
• Cybersecurity Practice: Practice on a public bug bounty program
(legally)
• Python: Advanced Automation and Orchestration
• Python Practice: Create a security automation workflow

� Day 50 � Review Day

• Cybersecurity: Hands-on Exploits & Privilege Escalation Labs
• Cybersecurity Practice: Complete an advanced penetration testing
scenario

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 • Python: Final Review of Advanced Python Applications
• Python Practice: Refine and integrate your security tools into a com-
prehensive framework

� Stage 4 (Mastery) - Focus Areas

� Cybersecurity: OSCP-like Hands-on Pentesting, Red Teaming, Exploit Writ-
ing, Bug Bounty � Python: Advanced Security Frameworks, AI/ML for Secu-
rity, Automation at Scale

� Day 51-60: Advanced Pentesting + Python Security Frameworks

� Day 51
• Cybersecurity: OSCP-Style Active Directory Attacks (BloodHound,
PowerView)
• Cybersecurity Practice: Complete a comprehensive AD attack lab
from enumeration to domain admin
• Python: Creating Advanced Security Frameworks
• Python Practice: Start building a modular security testing framework

� Day 52
• Cybersecurity: Privilege Escalation & Lateral Movement (Win-
dows/Linux)
• Cybersecurity Practice: Create a documented methodology for privi-
lege escalation
• Python: Advanced Web Application Security
• Python Practice: Extend your framework with web application testing
modules

� Day 53
• Cybersecurity: Bypassing Antivirus & EDR (Obfuscation, Packing)
• Cybersecurity Practice: Test various evasion techniques against mod-
ern AV
• Python: Custom Malware Analysis Platform
• Python Practice: Create a sandbox for analyzing suspicious files

� Day 54
• Cybersecurity: Red Teaming Simulation (MITRE ATT&CK, C2 Frame-
works)
• Cybersecurity Practice: Plan and document a red team engagement
using the MITRE framework
• Python: Integration with Security Tools and APIs
• Python Practice: Create connectors for various security tools and APIs

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� Day 55
• Cybersecurity: Kerberoasting, Pass-the-Hash, and NTLM Relay
• Cybersecurity Practice: Chain multiple credential attacks in a lab
environment
• Python: Real-Time Security Monitoring
• Python Practice: Create a real-time security event monitoring dash-
board

� Day 56
• Cybersecurity: Exploit Writing: Custom Buffer Overflow Attacks
• Cybersecurity Practice: Write an exploit from scratch for a specific
vulnerability
• Python: CI/CD Security Integration
• Python Practice: Create tools for DevSecOps pipeline integration

� Day 57
• Cybersecurity: Advanced CTF Challenges (HackTheBox, TryHackMe)
• Cybersecurity Practice: Complete an advanced difficulty box on Hack-
TheBox
• Python: Testing and Fuzzing Applications
• Python Practice: Create an advanced fuzzing framework

� Day 58
• Cybersecurity: Bug Bounty Hunting (Recon, Reporting, Responsible
Disclosure)
• Cybersecurity Practice: Create a bug bounty hunting methodology
and checklist
• Python: Performance Optimization for Security Tools
• Python Practice: Optimize your tools for speed and efficiency

� Day 59
• Cybersecurity: Final Red Teaming Simulation + Report Writing
• Cybersecurity Practice: Conduct a mock red team exercise and write
a professional report
• Python: Large-Scale Security Automation
• Python Practice: Create orchestration scripts for multiple security tools

� Day 60 � Review & Hands-on Day

• Cybersecurity: OSCP-like Challenge on HackTheBox
• Cybersecurity Practice: Complete a mock OSCP-style lab and docu-
ment methodology
• Python: Final Security Framework Review

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 • Python Practice: Finalize your custom security framework with docu-
mentation

� Day 61-75: Advanced Red Teaming + Python AI for Security

� Day 61
• Cybersecurity: Social Engineering & Physical Penetration Testing
• Cybersecurity Practice: Create a phishing campaign simulation
• Python: Machine Learning for Phishing Detection
• Python Practice: Build an ML model to identify phishing emails

� Day 62
• Cybersecurity: Advanced Wireless Attacks (WPA3, RADIUS)
• Cybersecurity Practice: Set up and test wireless security in a lab en-
vironment
• Python: Signal Processing for Wireless Security
• Python Practice: Create tools for wireless packet analysis

� Day 63
• Cybersecurity: Container Security (Docker, Kubernetes)
• Cybersecurity Practice: Identify and exploit container escape vulner-
abilities
• Python: Container Security Automation
• Python Practice: Build container security scanning tools

� Day 64
• Cybersecurity: Cloud Security (AWS, Azure, GCP)
• Cybersecurity Practice: Use cloud security tools to identify misconfig-
urations
• Python: Cloud Security Posture Management
• Python Practice: Create a cloud security assessment tool

� Day 65
• Cybersecurity: Advanced Malware Analysis
• Cybersecurity Practice: Analyze a complex malware sample and doc-
ument behavior
• Python: Dynamic Analysis Automation
• Python Practice: Create automated malware behavior analysis tools

� Day 66
• Cybersecurity: IoT Security & Hardware Hacking Basics

13
 • Cybersecurity Practice: Analyze and test an IoT device for vulnera-
bilities
• Python: IoT Device Analysis
• Python Practice: Create tools for IoT firmware analysis

� Day 67
• Cybersecurity: Mobile Application Security (Android, iOS)
• Cybersecurity Practice: Perform static and dynamic analysis of a mo-
bile app
• Python: Mobile App Security Testing Automation
• Python Practice: Create tools for automating mobile app security test-
ing

� Day 68
• Cybersecurity: Advanced Persistence Techniques
• Cybersecurity Practice: Implement and detect various persistence
mechanisms
• Python: Threat Hunting Automation
• Python Practice: Create a threat hunting platform with Python

� Day 69
• Cybersecurity: Supply Chain Attacks
• Cybersecurity Practice: Analyze a supply chain attack scenario
• Python: Software Composition Analysis
• Python Practice: Create a tool to identify vulnerable dependencies

� Day 70
• Cybersecurity: Custom C2 Framework Development
• Cybersecurity Practice: Design and implement a basic C2 communi-
cation channel
• Python: Steganography and Covert Channels
• Python Practice: Create tools for data exfiltration via covert channels

� Day 71
• Cybersecurity: Zero-Day Vulnerability Research
• Cybersecurity Practice: Follow a methodology to search for new vul-
nerabilities
• Python: Fuzzing and Automated Vulnerability Discovery
• Python Practice: Create custom fuzzing tools for specific targets

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� Day 72
• Cybersecurity: Advanced Exploit Development (ROP Chains)
• Cybersecurity Practice: Build a ROP chain exploit for ASLR bypass
• Python: Binary Exploitation Frameworks
• Python Practice: Create tools to assist in exploit development

� Day 73
• Cybersecurity: Red Team Infrastructure Setup
• Cybersecurity Practice: Set up a complete red team infrastructure
• Python: Red Team Automation
• Python Practice: Create tools for red team operation automation

� Day 74
• Cybersecurity: Advanced Evasion Techniques
• Cybersecurity Practice: Test various evasion techniques against secu-
rity tools
• Python: AI-based Evasion Detection
• Python Practice: Create an AI model to detect evasion attempts

� Day 75 � Review Day

• Cybersecurity: Comprehensive Red Team Assessment
• Cybersecurity Practice: Plan and document a complete red team op-
eration
• Python: AI/ML Security Framework
• Python Practice: Finalize your AI-enhanced security testing framework

� Day 76-90: Mock OSCP Exam + Advanced Security Automation

� Day 76-77
• Cybersecurity: Mock OSCP Exam Preparation
• Cybersecurity Practice: Review all techniques and methodologies
• Python: Comprehensive Testing Framework
• Python Practice: Integrate all your tools into a unified framework

� Day 78-79
• Cybersecurity: Mock OSCP Exam (24-hour hands-on pentesting)
• Cybersecurity Practice: Complete a full OSCP-style exam environ-
ment
• Python: Automated Reporting Tools
• Python Practice: Create automated report generation tools

15
� Day 80-81
• Cybersecurity: Professional Report Writing
• Cybersecurity Practice: Write a professional penetration testing report
• Python: Report Generation Automation
• Python Practice: Create templates and tools for automated report gen-
eration

� Day 82-83
• Cybersecurity: Top OSCP-Like Machines Review
• Cybersecurity Practice: Solve challenging machines and document
methodology
• Python: Attack Methodology Automation
• Python Practice: Create workflow automation for common attack pat-
terns

� Day 84-85
• Cybersecurity: Defensive Security Fundamentals
• Cybersecurity Practice: Set up monitoring and detection systems
• Python: Security Monitoring Automation
• Python Practice: Create a security operations dashboard

� Day 86-87
• Cybersecurity: Incident Response
• Cybersecurity Practice: Complete an incident response simulation
• Python: IR Automation and Forensics
• Python Practice: Create incident response automation tools

� Day 88-89
• Cybersecurity: Threat Intelligence
• Cybersecurity Practice: Analyze and apply threat intelligence data
• Python: Threat Intelligence Platforms
• Python Practice: Create a threat intelligence aggregation system

� Day 90 � Review Day

• Cybersecurity: Mock OSCP Exam Review
• Cybersecurity Practice: Identify strengths and weaknesses in your ap-
proach
• Python: Full Framework Testing
• Python Practice: Conduct comprehensive testing of your security frame-
work

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� Day 91-120: Full Practical Labs & Red Teaming
� Day 91-95
• Cybersecurity: Full OSCP-Style Labs (HackTheBox Pro, Virtual Hack-
ing Labs)
• Cybersecurity Practice: Complete 5-10 machines using a consistent
methodology
• Python: Specialized Security Tools Development
• Python Practice: Create tools for specific security testing scenarios

� Day 96-100
• Cybersecurity: Red Teaming Simulation: MITRE ATT&CK Frame-
work
• Cybersecurity Practice: Plan and simulate a full-scope red team en-
gagement
• Python: Red Team Automation Framework
• Python Practice: Create tools for each phase of the red team engage-
ment

� Day 101-105
• Cybersecurity: Custom Exploit Writing (Python, Shellcode Develop-
ment)
• Cybersecurity Practice: Develop exploits for specific vulnerabilities
• Python: Exploit Development Framework
• Python Practice: Create a framework for exploit development and test-
ing

� Day 106-110
• Cybersecurity: Bug Bounty Hunting: Practical Hunting & Report Writ-
ing
• Cybersecurity Practice: Participate in public bug bounty programs
• Python: Bug Bounty Automation Tools
• Python Practice: Create tools to streamline bug bounty hunting

� Day 111-115
• Cybersecurity: Advanced Active Directory and Azure AD Attacks
• Cybersecurity Practice: Set up and attack a complex AD environment
• Python: Enterprise Security Assessment Tools
• Python Practice: Create tools for enterprise security assessment

� Day 116-120 � Review Period

• Cybersecurity: Project Work: Comprehensive Pentesting Report

17
 • Cybersecurity Practice: Create a professional security assessment re-
port
• Python: Enterprise-Grade Security Suite
• Python Practice: Finalize your comprehensive security testing suite

� Day 121-150: OSCP Exam Prep + Advanced Security Automation

� Day 121-125
• Cybersecurity: 24-Hour OSCP Mock Exams (TryHackMe / HackThe-
Box Labs)
• Cybersecurity Practice: Complete multiple mock exam scenarios
• Python: Advanced Exploitation Frameworks
• Python Practice: Create specialized tools for common exploitation sce-
narios

� Day 126-130
• Cybersecurity: Privilege Escalation Mastery (Windows & Linux)
• Cybersecurity Practice: Document and practice all privilege escalation
techniques
• Python: Privilege Escalation Automation
• Python Practice: Create tools to streamline privilege escalation

� Day 131-135
• Cybersecurity: Red Team Infrastructure Setup (C2 Frameworks)
• Cybersecurity Practice: Set up and manage a complete red team in-
frastructure
• Python: Custom C2 Channel Development
• Python Practice: Create custom command and control channels

� Day 136-140
• Cybersecurity: Bug Bounty & Vulnerability Research
• Cybersecurity Practice: Actively participate in bug bounty programs
• Python: Vulnerability Research Automation
• Python Practice: Create tools for vulnerability discovery and validation

� Day 141-145
• Cybersecurity: Advanced Evasion & Defense Bypass
• Cybersecurity Practice: Test various evasion techniques against secu-
rity solutions
• Python: AI for Evasion and Detection
• Python Practice: Create AI models for both evasion and detection

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� Day 146-150 � Review Period
• Cybersecurity: Final OSCP Preparation and Review
• Cybersecurity Practice: Final review of all techniques and methodolo-
gies
• Python: Complete Security Suite Integration
• Python Practice: Final review and integration of all developed tools

� Day 151-180: Real-World Cybersecurity & Python Mastery

� Day 151-155
• Cybersecurity: Final OSCP Exam Attempt / Professional Certification
• Cybersecurity Practice: Focus on exam preparation and methodology
• Python: Professional Security Tool Development
• Python Practice: Finalize and document your

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