Amy's Cybersecurity Study Plan

About This Plan

Student

Amy, 37

Background

Stay-at-home mum, no prior IT education

Study Time

15 hours/week (3 days x 5 hours)

Goal

Career transition into cybersecurity

The Five Phases

1

Computer & Networking Fundamentals

Weeks 1-4

Understand how computers and networks work

Week 1: How computers work + Command Line basics
Week 2: More CLI, file permissions, text editors
Week 3: Networking fundamentals (IP, DNS, ports)
Week 4: Security mindset + environment setup

Jump to Phase 1

2

Python Foundations

Weeks 5-16

Write basic Python programs confidently

Week 5: Getting started - variables, data types
Week 6: Control flow - if/elif/else
Week 7: Loops - while and for
Week 8: Functions
Week 9: Lists
Week 10: Dictionaries
Week 11: String manipulation
Week 12: File I/O
Week 13: Error handling
Week 14: Modules and packages
Week 15: Regular expressions
Week 16: Capstone project - Password checker

Jump to Phase 2

3

Python for Security

Weeks 17-24

Apply Python to security-relevant tasks

Weeks 17-18: Working with APIs and JSON
Weeks 19-20: Network programming with sockets
Weeks 21-22: Web scraping and automation
Weeks 23-24: Security automation project

View Phase 3 Details

4

Security Fundamentals

Weeks 25-36

Understand core security concepts and tools

Weeks 25-28: Security principles, CIA triad, threat modelling
Weeks 29-32: Linux security, OWASP Top 10
Weeks 33-36: Hands-on practice (TryHackMe, HackTheBox)

View Phase 4 Details

5

Specialisation & Certification

Weeks 37+

Earn Security+ certification, build portfolio

Weeks 37-44: CompTIA Security+ preparation
Weeks 45-48: Portfolio projects
Weeks 49+: Job preparation and applications

View Phase 5 Details

Realistic Milestones

6-9 months: Comfortable with Python, basic security concepts
12-18 months: Ready for entry-level certification (CompTIA Security+)
18-24 months: Portfolio projects complete, ready to apply for junior roles

Week 1: How Computers Work + Command Line

Phase 1

Learning Objectives

Understand basic hardware components (CPU, RAM, storage)
Know what an operating system does
Navigate the file system using command line
Set up a Linux virtual machine for practice

Day 1 (5 hours)

Time	Activity	Resource
1.5 hrs	Watch CS50 Week 0 lecture - Introduction to Computer Science	CS50 YouTube
1.5 hrs	Watch "How Computers Work" playlist by Code.org	Code.org Playlist
2 hrs	Download and install VirtualBox + Ubuntu What is Linux? Linux is a free operating system (like Windows or macOS). Most cybersecurity work happens on Linux because: Most servers on the internet run Linux Most hacking/security tools are built for Linux It gives you more control and teaches you how computers really work Ubuntu is a beginner-friendly version of Linux - perfect for learning. What is a Virtual Machine? A virtual machine (VM) is like a computer inside your computer. It lets you run Linux without replacing Windows/macOS. Think of it as a safe "sandbox" to experiment in If you break something, just delete it and start fresh Your real computer stays untouched VirtualBox is free software that creates these virtual machines. Watch First (before installing) What is Linux? (6 min) What is a Virtual Machine? (5 min)	VirtualBox \| Ubuntu

Day 2 (5 hours)

Time	Activity	Resource
1 hr	Complete Ubuntu installation in VirtualBox	Ubuntu VM Tutorial
2 hrs	Read Ubuntu's "Command Line for Beginners" tutorial	Ubuntu CLI Tutorial
2 hrs	Practice basic commands: ls, cd, pwd, mkdir, cp, mv, rm, cat	Practice in your Ubuntu VM

Day 3 (5 hours)

Time	Activity	Resource
2 hrs	Watch "Linux Commands for Beginners" (first 2 hours)	YouTube Tutorial
3 hrs	Hands-on Practice: Navigate your Ubuntu system entirely via terminal	Create folders, move files, explore the file system

Commands to Master This Week

ls          # list files in current directory
cd          # change directory
pwd         # print working directory (where am I?)
mkdir       # make a new directory
cp          # copy files
mv          # move or rename files
rm          # remove/delete files
cat         # display file contents
clear       # clear the terminal screen

Week 1 Milestone

Can explain what RAM and storage are to someone else
Have a working Ubuntu VM
Can navigate the file system using only terminal commands

Week 2: More Command Line + Text Editors

Phase 1

Learning Objectives

Understand file permissions and why they matter
Learn to use sudo (administrator privileges)
Edit files from the command line
Install software using package managers

Day 1 (5 hours)

Time	Activity	Resource
2 hrs	Continue "Linux Commands for Beginners" video	YouTube Tutorial
1.5 hrs	Read about Linux file permissions	Linux Journey - Permissions
1.5 hrs	Practice: Check and change file permissions with chmod	Practice in your Ubuntu VM

Day 2 (5 hours)

Time	Activity	Resource
1 hr	Learn about nano text editor	Nano Tutorial
2 hrs	Practice creating and editing files with nano	Create text files, edit them, save and exit
2 hrs	Learn about sudo and package management (apt)	Ubuntu Package Management

Day 3 (5 hours)

Time	Activity	Resource
2 hrs	Install software using apt (Python, git, curl)	Run: `sudo apt update && sudo apt install python3 git curl`
1 hr	Learn about environment variables and PATH	Environment Variables Guide
2 hrs	Mini-project: Create a folder structure for your studies using only terminal	Create folders for each phase, create README files

Commands to Master This Week

sudo        # run command as administrator
chmod       # change file permissions
nano        # simple text editor
apt update  # update available software list
apt install # install new software
echo        # print text to screen
which       # find where a program is located
man         # read manual pages for commands

Week 2 Milestone

Can install software on Linux using apt
Can create and edit text files without a graphical interface
Understand why "permission denied" errors occur

Week 3: Networking Fundamentals

Phase 1

Learning Objectives

Understand how the internet works
Know what IP addresses, DNS, and ports are
Use basic networking commands
Trace what happens when you visit a website

Day 1 (5 hours)

Time	Activity	Resource
3 hrs	Watch NetworkChuck's FREE CCNA playlist (first 5 videos)	NetworkChuck CCNA
2 hrs	Take notes on: networks, switches, routers, IP addresses	Use nano to create a notes file

Day 2 (5 hours)

Time	Activity	Resource
2 hrs	Continue NetworkChuck videos (TCP/IP and OSI model)	Same playlist
1 hr	Read: "How DNS Works" (interactive comic)	How DNS Works
2 hrs	Hands-on: Use ping, ifconfig, nslookup in terminal	Practice finding IP addresses, checking connectivity

Day 3 (5 hours)

Time	Activity	Resource
2 hrs	Learn about HTTP and ports	MDN HTTP Overview
1 hr	Use browser developer tools (F12) to watch network requests	Visit websites and observe the Network tab
2 hrs	Mini-project: Write out what happens when you type "google.com"	Document DNS lookup, TCP connection, HTTP request/response

Commands to Master This Week

ping        # test if a host is reachable
ifconfig    # show network interface info (or use 'ip a')
nslookup    # look up DNS records
traceroute  # show the path packets take to reach a host
netstat     # show network connections
curl        # make HTTP requests from command line

Week 3 Milestone

Can explain what happens when you visit a website
Know the difference between IP address and MAC address
Understand what ports are and why they matter for security

Week 4: Security Mindset + Environment Setup

Phase 1

Learning Objectives

Understand why cybersecurity matters
Learn about different security career paths
Set up your complete study environment
Get motivated by real security stories

Day 1 (5 hours)

Time	Activity	Resource
2 hrs	Listen to Darknet Diaries episodes (pick 2 interesting ones)	Darknet Diaries (Recommended: Ep 29 "Stuxnet", Ep 33 "RockYou")
1.5 hrs	Read about major security breaches	Search: "Equifax breach explained", "Colonial Pipeline hack"
1.5 hrs	Learn about cybersecurity career paths	CyberSeek Career Pathway

Day 2 (5 hours)

Time	Activity	Resource
2 hrs	Install VS Code on your Ubuntu VM	VS Code Linux Setup
1 hr	Configure VS Code with Python extension	Install "Python" extension from marketplace
2 hrs	Create organised folder structure for your studies	Set up folders for each phase, each week

Day 3 (5 hours)

Time	Activity	Resource
1 hr	Create a TryHackMe account	TryHackMe (free tier)
2 hrs	Complete "Starting Out in Cyber Sec" room	Starting Out Room
1 hr	Create a GitHub account	GitHub
1 hr	Review Phase 1, create summary notes	Consolidate what you've learned

Week 4 Milestone

Have a fully configured study environment (Ubuntu VM + VS Code + Python)
Completed your first TryHackMe room
Can explain different cybersecurity roles to someone
Feel motivated and excited to continue

Phase 1 Complete!

You now understand the basics of computers, command line, and networking. Time to learn Python!

Week 5: Python Basics - Getting Started

Phase 2

Learning Objectives

Run Python programs
Use variables and basic data types
Get user input and display output

Day 1 (5 hours)

Time	Activity	Resource
2 hrs	Read ATBS Chapter 0: Introduction	Chapter 0
1 hr	Watch: Python Installation and Setup	Corey Schafer
2 hrs	Set up Python in VS Code, run your first program	Print "Hello, World!"

Day 2 (5 hours)

Time	Activity	Resource
2 hrs	Read ATBS Chapter 1: Python Basics	Chapter 1
3 hrs	Code Along: Type out ALL examples (don't copy-paste!)	Practice in VS Code

Day 3 (5 hours)

Time	Activity	Resource
2 hrs	Watch Corey Schafer: Strings, Integers, Floats	Data Types Video
3 hrs	Practice: Write at least 5 small programs	See practice exercises below

Practice Programs to Write

# 1. Greeting program
name = input("What is your name? ")
print("Hello, " + name + "!")

# 2. Basic calculator
num1 = int(input("First number: "))
num2 = int(input("Second number: "))
print("Sum:", num1 + num2)

# 3. Age in days calculator
age = int(input("Your age in years: "))
days = age * 365
print("You have lived approximately", days, "days")

# 4. Mad libs game
adjective = input("Enter an adjective: ")
noun = input("Enter a noun: ")
print(f"The {adjective} {noun} jumped over the fence.")

# 5. Temperature converter
celsius = float(input("Temperature in Celsius: "))
fahrenheit = (celsius * 9/5) + 32
print(f"{celsius}C = {fahrenheit}F")

Week 5 Milestone

Can run Python programs in VS Code
Understand variables, strings, and numbers
Completed at least 5 practice programs

Week 6: Control Flow - Making Decisions (if/else)

Phase 2

Learning Objectives

Use comparison operators
Write if/elif/else statements
Combine conditions with and/or/not

Day 1 (5 hours)

Time	Activity	Resource
2 hrs	Read ATBS Chapter 2 (first half - Flow Control)	Chapter 2
3 hrs	Code Along: Type out all if/else examples	Practice in VS Code

Day 2 (5 hours)

Time	Activity	Resource
1.5 hrs	Watch Corey Schafer: Conditionals and Booleans	Conditionals Video
3.5 hrs	Practice Programs: Write programs using if/else	See exercises below

Day 3 (5 hours)

Time	Activity	Resource
5 hrs	Practice: More conditional programs + review	Complete all exercises below

Practice Programs to Write

# 1. Password checker
password = input("Enter password: ")
if password == "secret123":
    print("Access granted!")
else:
    print("Access denied!")

# 2. Grade calculator
score = int(input("Enter your score (0-100): "))
if score >= 90:
    print("Grade: A")
elif score >= 80:
    print("Grade: B")
elif score >= 70:
    print("Grade: C")
elif score >= 60:
    print("Grade: D")
else:
    print("Grade: F")

# 3. Age validator
age = int(input("Enter your age: "))
if age < 0 or age > 120:
    print("Invalid age!")
elif age < 13:
    print("You are a child")
elif age < 20:
    print("You are a teenager")
elif age < 65:
    print("You are an adult")
else:
    print("You are a senior")

# 4. Login system (multiple conditions)
username = input("Username: ")
password = input("Password: ")
if username == "admin" and password == "admin123":
    print("Welcome, administrator!")
elif username == "guest":
    print("Welcome, guest! Limited access.")
else:
    print("Invalid credentials")

Week 6 Milestone

Can write programs that make decisions
Understand ==, !=, <, >, <=, >=
Can combine conditions with and, or, not

Week 7: Control Flow - Loops

Phase 2

Learning Objectives

Write while loops
Write for loops
Use range() function
Know when to use break and continue

Day 1 (5 hours)

Time	Activity	Resource
2 hrs	Read ATBS Chapter 2 (second half - Loops)	Chapter 2
3 hrs	Code Along: Type out all loop examples	Practice in VS Code

Day 2 (5 hours)

Time	Activity	Resource
1.5 hrs	Watch Corey Schafer: Loops and Iterations	Loops Video
3.5 hrs	Practice Programs: Write programs using loops	See exercises below

Day 3 (5 hours)

Time	Activity	Resource
5 hrs	Practice: More loop programs + chapter exercises	Complete all exercises

Practice Programs to Write

# 1. Countdown
for i in range(10, 0, -1):
    print(i)
print("Blastoff!")

# 2. Password with limited attempts
attempts = 3
while attempts > 0:
    password = input("Enter password: ")
    if password == "secret":
        print("Access granted!")
        break
    attempts -= 1
    print(f"Wrong! {attempts} attempts remaining.")
else:
    print("Account locked!")

# 3. Sum calculator
total = 0
while True:
    num = input("Enter a number (or 'done' to finish): ")
    if num == "done":
        break
    total += int(num)
print(f"Total: {total}")

# 4. Multiplication table
number = int(input("Enter a number: "))
for i in range(1, 11):
    print(f"{number} x {i} = {number * i}")

# 5. Guessing game
import random
secret = random.randint(1, 100)
guesses = 0
while True:
    guess = int(input("Guess the number (1-100): "))
    guesses += 1
    if guess < secret:
        print("Too low!")
    elif guess > secret:
        print("Too high!")
    else:
        print(f"Correct! You got it in {guesses} guesses!")
        break

Week 7 Milestone

Can write while loops and for loops
Know when to use break and continue
Understand the range() function

Week 8: Functions

Phase 2

Learning Objectives

Define and call functions
Use parameters and return values
Understand variable scope

Day 1-2 (10 hours)

Time	Activity	Resource
2 hrs	Read ATBS Chapter 3: Functions	Chapter 3
3 hrs	Code Along: Type out all function examples	Practice in VS Code
1.5 hrs	Watch Corey Schafer: Functions	Functions Video
3.5 hrs	Practice: Rewrite previous programs using functions	Refactor your existing code

Practice Programs to Write

# 1. Greeting function
def greet(name):
    return f"Hello, {name}!"

print(greet("Amy"))
print(greet("World"))

# 2. Password validator
def is_valid_password(password):
    if len(password) < 8:
        return False
    if password.isalpha():  # only letters, no numbers
        return False
    return True

pwd = input("Create a password: ")
if is_valid_password(pwd):
    print("Password accepted!")
else:
    print("Password must be at least 8 characters with numbers")

# 3. Calculator with functions
def add(a, b):
    return a + b

def subtract(a, b):
    return a - b

def multiply(a, b):
    return a * b

def divide(a, b):
    if b == 0:
        return "Cannot divide by zero"
    return a / b

print(add(5, 3))        # 8
print(multiply(4, 7))   # 28
print(divide(10, 2))    # 5.0

Week 8 Milestone

Can define and use functions
Understand parameters and return values
Can refactor code to use functions

Week 9: Lists

Phase 2

Learning Objectives

Create and modify lists
Access list items with indexing and slicing
Use common list methods
Loop through lists

Day 1-2 (10 hours)

Time	Activity	Resource
2.5 hrs	Read ATBS Chapter 4: Lists	Chapter 4
2.5 hrs	Code Along: Type out all list examples	Practice in VS Code
1.5 hrs	Watch Corey Schafer: Lists, Tuples, Sets	Lists Video
3.5 hrs	Practice Programs	See exercises below

Practice Programs to Write

# 1. Shopping list manager
shopping_list = []

while True:
    print("\n1. Add item")
    print("2. Remove item")
    print("3. Show list")
    print("4. Quit")

    choice = input("Choose: ")

    if choice == "1":
        item = input("Item to add: ")
        shopping_list.append(item)
        print(f"Added {item}")
    elif choice == "2":
        item = input("Item to remove: ")
        if item in shopping_list:
            shopping_list.remove(item)
            print(f"Removed {item}")
        else:
            print("Item not found")
    elif choice == "3":
        print("\nYour shopping list:")
        for i, item in enumerate(shopping_list, 1):
            print(f"{i}. {item}")
    elif choice == "4":
        break

# 2. Find common items
list1 = [1, 2, 3, 4, 5]
list2 = [4, 5, 6, 7, 8]
common = []
for item in list1:
    if item in list2:
        common.append(item)
print(f"Common items: {common}")

Week 9 Milestone

Can create and modify lists
Understand indexing (including negative indices)
Can loop through lists with for loops

Week 10: Dictionaries

Phase 2

Learning Objectives

Create and use dictionaries
Access and modify dictionary values
Loop through dictionaries
Know when to use lists vs dictionaries

Day 1-2 (10 hours)

Time	Activity	Resource
2.5 hrs	Read ATBS Chapter 5: Dictionaries	Chapter 5
2.5 hrs	Code Along: Type out all dictionary examples	Practice in VS Code
1.5 hrs	Watch Corey Schafer: Dictionaries	Dictionaries Video
3.5 hrs	Practice Programs	See exercises below

Practice Programs to Write

# 1. Contact book
contacts = {}

while True:
    print("\n1. Add contact")
    print("2. Look up contact")
    print("3. List all contacts")
    print("4. Quit")

    choice = input("Choose: ")

    if choice == "1":
        name = input("Name: ")
        phone = input("Phone: ")
        email = input("Email: ")
        contacts[name] = {"phone": phone, "email": email}
        print(f"Added {name}")
    elif choice == "2":
        name = input("Name to look up: ")
        if name in contacts:
            print(f"Phone: {contacts[name]['phone']}")
            print(f"Email: {contacts[name]['email']}")
        else:
            print("Contact not found")
    elif choice == "3":
        for name, info in contacts.items():
            print(f"{name}: {info['phone']}")
    elif choice == "4":
        break

# 2. Word frequency counter
text = "the cat sat on the mat the cat was happy"
words = text.split()
frequency = {}

for word in words:
    frequency[word] = frequency.get(word, 0) + 1

print("Word frequencies:")
for word, count in frequency.items():
    print(f"  {word}: {count}")

Week 10 Milestone

Can create and use dictionaries
Understand when to use lists vs dictionaries
Can work with nested dictionaries

Week 11: Strings

Phase 2

Learning Objectives

Use string methods effectively
Format strings (f-strings)
Search and manipulate text
Parse and extract information from strings

Day 1-2 (10 hours)

Time	Activity	Resource
2.5 hrs	Read ATBS Chapter 6: Strings	Chapter 6
2.5 hrs	Code Along: Type out all string examples	Practice in VS Code
1.5 hrs	Watch Corey Schafer: Strings	Strings Video
3.5 hrs	Practice: Security-relevant string parsing	See exercises below

Practice Programs to Write

# 1. Password strength checker
def check_password_strength(password):
    has_upper = any(c.isupper() for c in password)
    has_lower = any(c.islower() for c in password)
    has_digit = any(c.isdigit() for c in password)
    has_special = any(c in "!@#$%^&*" for c in password)
    long_enough = len(password) >= 8

    score = sum([has_upper, has_lower, has_digit, has_special, long_enough])

    if score == 5:
        return "Very Strong"
    elif score >= 4:
        return "Strong"
    elif score >= 3:
        return "Medium"
    else:
        return "Weak"

password = input("Enter password to check: ")
print(f"Strength: {check_password_strength(password)}")

# 2. Simple log parser (security relevant!)
log = "2024-01-15 14:23:01 ERROR Connection failed from 192.168.1.100"

parts = log.split()
date = parts[0]
time = parts[1]
level = parts[2]
message = " ".join(parts[3:])

print(f"Date: {date}")
print(f"Time: {time}")
print(f"Level: {level}")
print(f"Message: {message}")

Week 11 Milestone

Know common string methods (split, join, strip, etc.)
Can format strings with f-strings
Can parse and extract information from text

Week 12: File Input/Output

Phase 2

Learning Objectives

Read from files
Write to files
Use the 'with' statement
Work with file paths

Day 1-2 (10 hours)

Time	Activity	Resource
2.5 hrs	Read ATBS Chapter 9: Reading and Writing Files	Chapter 9
2.5 hrs	Code Along: Type out all file examples	Create test files to work with
1.5 hrs	Watch Corey Schafer: File Objects	File I/O Video
3.5 hrs	Practice: Create a log file analyzer	This is security-relevant!

Practice Programs to Write

# 1. Basic file reading and writing
with open("notes.txt", "w") as f:
    f.write("My Python Learning Notes\n")
    f.write("========================\n")
    f.write("Week 12: File I/O\n")

with open("notes.txt", "r") as f:
    content = f.read()
    print(content)

# 2. Log file analyzer (VERY security relevant!)
def analyze_log(filename):
    stats = {
        "total_lines": 0,
        "errors": 0,
        "warnings": 0,
        "info": 0,
        "ips": set()
    }

    try:
        with open(filename, "r") as f:
            for line in f:
                stats["total_lines"] += 1

                if "ERROR" in line:
                    stats["errors"] += 1
                elif "WARNING" in line:
                    stats["warnings"] += 1
                elif "INFO" in line:
                    stats["info"] += 1

        return stats
    except FileNotFoundError:
        return None

# 3. Save and load data with JSON
import json

contacts = {"Alice": "555-1234", "Bob": "555-5678"}
with open("contacts.json", "w") as f:
    json.dump(contacts, f, indent=2)

with open("contacts.json", "r") as f:
    loaded = json.load(f)
    print(loaded)

Week 12 Milestone

Can read from and write to files
Understand the 'with' statement
Created a working log analyzer

Week 13: Error Handling

Phase 2

Learning Objectives

Understand different types of errors
Use try/except blocks
Handle errors gracefully
Make robust programs

Day 1-2 (10 hours)

Time	Activity	Resource
2.5 hrs	Read ATBS Chapter 11: Debugging (error handling section)	Chapter 11
2.5 hrs	Code Along: Practice try/except examples	Intentionally cause errors and catch them
2 hrs	Watch: Python Try/Except for Error Handling	Corey Schafer
3 hrs	Revisit old programs: Add error handling	Make them crash-proof

Practice Programs to Write

# 1. Safe number input
def get_number(prompt):
    while True:
        try:
            return int(input(prompt))
        except ValueError:
            print("Please enter a valid number!")

age = get_number("Enter your age: ")
print(f"You are {age} years old")

# 2. Safe file reader
def read_file_safely(filename):
    try:
        with open(filename, "r") as f:
            return f.read()
    except FileNotFoundError:
        print(f"Error: File '{filename}' not found")
        return None
    except PermissionError:
        print(f"Error: No permission to read '{filename}'")
        return None

content = read_file_safely("test.txt")
if content:
    print(content)

Week 13 Milestone

Understand try/except/finally
Can catch specific exceptions
Old programs are now crash-proof

Week 14: Modules and Packages

Phase 2

Learning Objectives

Import and use modules
Explore the standard library
Install packages with pip
Use virtual environments

Day 1-2 (10 hours)

Time	Activity	Resource
2 hrs	Read ATBS Chapter 7 (import/module part)	Chapter 7
1.5 hrs	Explore Python Standard Library documentation	Python Docs
2 hrs	Learn pip and virtual environments	Real Python Guide
2.5 hrs	Create a virtual environment, install requests library	`python -m venv myenv` then `pip install requests`
2 hrs	Practice: Security-relevant modules	See exercises below

Key Modules for Security

import os          # Operating system interface
import sys         # System-specific parameters
import datetime    # Date and time
import hashlib     # Hashing (important for security!)
import json        # JSON parsing
import re          # Regular expressions (next week)
import requests    # HTTP requests (installed via pip)

# Example: Cryptographic hashing (SECURITY!)
import hashlib

password = "mysecretpassword"
hashed = hashlib.sha256(password.encode()).hexdigest()
print(f"SHA256: {hashed}")

# Example: Secure random tokens
import secrets

secure_token = secrets.token_hex(16)
print(f"Secure token: {secure_token}")

Week 14 Milestone

Can import and use standard library modules
Know how to use pip to install packages
Understand virtual environments
Used hashlib for hashing (security skill!)

Week 15: Regular Expressions

Phase 2

Learning Objectives

Understand regex patterns
Use the re module
Extract data from text using patterns
This is CRITICAL for security log analysis

Day 1-2 (10 hours)

Time	Activity	Resource
2.5 hrs	Read ATBS Chapter 7: Pattern Matching with Regular Expressions	Chapter 7
2.5 hrs	Practice on regex101.com (select Python flavor)	regex101
2 hrs	Read Python's Regular Expression HOWTO	Python Regex HOWTO
3 hrs	Practice: Write regex for security data	IPs, emails, timestamps

Practice Programs to Write

import re

# 1. Find all IP addresses in text
text = """
Failed login attempt from 192.168.1.100
Successful connection from 10.0.0.55
Warning: Multiple attempts from 172.16.0.1
"""

ip_pattern = r'\d{1,3}\.\d{1,3}\.\d{1,3}\.\d{1,3}'
ips = re.findall(ip_pattern, text)
print(f"Found IPs: {ips}")

# 2. Validate email addresses
def is_valid_email(email):
    pattern = r'^[\w\.-]+@[\w\.-]+\.\w+$'
    return bool(re.match(pattern, email))

# 3. Parse log entries with regex
log_line = "2024-01-15 14:23:01 ERROR [auth] Failed login for user admin from 192.168.1.100"

pattern = r'(\d{4}-\d{2}-\d{2}) (\d{2}:\d{2}:\d{2}) (\w+) \[(\w+)\] (.+)'
match = re.match(pattern, log_line)

if match:
    date, time, level, component, message = match.groups()
    print(f"Date: {date}")
    print(f"Time: {time}")
    print(f"Level: {level}")
    print(f"Component: {component}")
    print(f"Message: {message}")

Week 15 Milestone

Can write basic regex patterns
Know how to use regex101.com to test patterns
Can extract IPs, emails, timestamps from text

Week 16: Consolidation Project - Security Log Analyzer

Phase 2 Final

This week, you'll build a complete security tool!

Project Requirements

Read a log file
Parse each line using regex
Count events by severity (ERROR, WARNING, INFO)
Extract and list unique IP addresses
Identify potential brute force attempts
Save a security report to a file

Day 1 (5 hours)

Time	Activity
1 hr	Plan the project structure (write pseudocode first)
4 hrs	Build the core log parsing functionality

Day 2 (5 hours)

Time	Activity
5 hrs	Add analysis features: IP extraction, event counting, brute force detection

Day 3 (5 hours)

Time	Activity
3 hrs	Add report generation and error handling
2 hrs	Test thoroughly, fix bugs, clean up code

Project Template

#!/usr/bin/env python3
"""
Security Log Analyzer
A tool to analyze security logs and identify potential threats.
"""

import re
from datetime import datetime
from collections import Counter

def parse_log_line(line):
    """Parse a single log line and return structured data."""
    pattern = r'(\d{4}-\d{2}-\d{2}) (\d{2}:\d{2}:\d{2}) (\w+) (.+)'
    match = re.match(pattern, line)

    if match:
        return {
            'date': match.group(1),
            'time': match.group(2),
            'level': match.group(3),
            'message': match.group(4)
        }
    return None

def extract_ips(text):
    """Extract all IP addresses from text."""
    pattern = r'\d{1,3}\.\d{1,3}\.\d{1,3}\.\d{1,3}'
    return re.findall(pattern, text)

def analyze_log_file(filename):
    """Analyze entire log file and return statistics."""
    stats = {
        'total_lines': 0,
        'levels': Counter(),
        'ips': Counter(),
        'failed_logins': Counter(),
        'events': []
    }

    try:
        with open(filename, 'r') as f:
            for line in f:
                line = line.strip()
                if not line:
                    continue

                stats['total_lines'] += 1
                parsed = parse_log_line(line)

                if parsed:
                    stats['levels'][parsed['level']] += 1
                    stats['events'].append(parsed)

                    ips = extract_ips(line)
                    for ip in ips:
                        stats['ips'][ip] += 1

                    if 'failed' in parsed['message'].lower() and 'login' in parsed['message'].lower():
                        for ip in ips:
                            stats['failed_logins'][ip] += 1

        return stats

    except FileNotFoundError:
        print(f"Error: File '{filename}' not found")
        return None

def detect_brute_force(stats, threshold=5):
    """Find IPs with multiple failed login attempts."""
    suspicious = []
    for ip, count in stats['failed_logins'].items():
        if count >= threshold:
            suspicious.append((ip, count))
    return sorted(suspicious, key=lambda x: x[1], reverse=True)

def generate_report(stats, output_file):
    """Write analysis results to file."""
    with open(output_file, 'w') as f:
        f.write("=" * 50 + "\n")
        f.write("SECURITY LOG ANALYSIS REPORT\n")
        f.write(f"Generated: {datetime.now().strftime('%Y-%m-%d %H:%M:%S')}\n")
        f.write("=" * 50 + "\n\n")

        f.write(f"Total log entries analyzed: {stats['total_lines']}\n\n")

        f.write("EVENT SUMMARY:\n")
        for level, count in stats['levels'].most_common():
            f.write(f"  {level}: {count}\n")
        f.write("\n")

        f.write("TOP IP ADDRESSES:\n")
        for ip, count in stats['ips'].most_common(10):
            f.write(f"  {ip}: {count} occurrences\n")
        f.write("\n")

        suspicious = detect_brute_force(stats)
        if suspicious:
            f.write("[!] POTENTIAL BRUTE FORCE ATTEMPTS:\n")
            for ip, count in suspicious:
                f.write(f"  {ip}: {count} failed login attempts\n")
        else:
            f.write("No brute force attempts detected.\n")

    print(f"Report saved to {output_file}")

def main():
    """Main function to run the analyzer."""
    print("Security Log Analyzer")
    print("-" * 30)

    log_file = input("Enter log file path: ")

    print(f"\nAnalyzing {log_file}...")
    stats = analyze_log_file(log_file)

    if stats:
        print(f"Processed {stats['total_lines']} log entries")
        print(f"\nErrors: {stats['levels'].get('ERROR', 0)}")
        print(f"Warnings: {stats['levels'].get('WARNING', 0)}")
        print(f"Unique IPs: {len(stats['ips'])}")

        suspicious = detect_brute_force(stats)
        if suspicious:
            print(f"\n[!] {len(suspicious)} IPs with suspicious activity!")

        report_file = log_file.rsplit('.', 1)[0] + '_report.txt'
        generate_report(stats, report_file)

if __name__ == "__main__":
    main()

Week 16 Milestone

Completed a working security log analyzer
Program handles errors gracefully
Can analyze real log files and detect suspicious activity

Phase 2 Complete!

Congratulations! You now have solid Python foundations and have built your first security tool!

Future Phases Overview

Phase 3: Python for Security (Weeks 17-24)

Goal: Apply your Python skills to security-relevant tasks and automation

Weeks 17-18: Working with APIs and JSON

Topics:

Understanding REST APIs
HTTP methods (GET, POST, PUT, DELETE)
JSON format and parsing
Using the requests library
API authentication (API keys, tokens)

Mini-Projects:

Query a public API (e.g., weather, IP geolocation)
Build a VirusTotal file checker script
Create an IP reputation checker using AbuseIPDB

Resources: Real Python - Requests | VirusTotal API

Weeks 19-20: Network Programming with Sockets

Topics:

TCP vs UDP protocols
Python socket module basics
Creating client-server applications
Port scanning concepts
Banner grabbing techniques

Mini-Projects:

Build a simple port scanner
Create a basic chat client/server
Write a banner grabbing tool

Resources: Real Python - Sockets | Python Socket Docs

Weeks 21-22: Web Scraping and Automation

Topics:

HTML structure and parsing
Using BeautifulSoup library
Handling pagination
Ethical scraping practices
Automating repetitive tasks

Mini-Projects:

Scrape security news headlines
Extract CVE information from NIST
Automate log file parsing

Resources: ATBS - Web Scraping | BeautifulSoup Docs

Weeks 23-24: Security Automation Project

Topics:

Combining all learned skills
Project planning and design
Error handling in security tools
Logging and reporting
Code documentation

Capstone Project Ideas:

Network reconnaissance tool
Automated vulnerability report generator
Security log analyzer
Threat intelligence aggregator

Phase 4: Security Fundamentals (Weeks 25-36)

Goal: Build a strong foundation in cybersecurity principles and hands-on skills

Weeks 25-28: Security Principles & Threat Modelling

Topics:

CIA Triad (Confidentiality, Integrity, Availability)
Authentication vs Authorization
Defence in Depth strategy
Threat modelling frameworks (STRIDE)
Risk assessment basics
Security policies and procedures

Activities:

Create a threat model for a web application
Analyse a real security breach case study
Write a basic security policy document

Resources: TryHackMe - Intro to Security | OWASP Threat Modelling

Weeks 29-32: Linux Security & Common Attacks

Topics:

Linux hardening basics
Firewall configuration (iptables/ufw)
OWASP Top 10 vulnerabilities
SQL Injection attacks
Cross-Site Scripting (XSS)
Authentication bypasses
Password attacks and cracking

Activities:

Harden a Linux server (checklist-based)
Practice OWASP vulnerabilities on DVWA
Complete TryHackMe OWASP rooms

Resources: OWASP Top 10 | DVWA Room | PortSwigger Web Security Academy

Weeks 33-36: Hands-On Practice

Topics:

Reconnaissance and enumeration
Vulnerability scanning (Nmap, Nikto)
Exploitation basics (Metasploit intro)
Post-exploitation concepts
Report writing for findings

Platforms & Activities:

Complete TryHackMe learning paths
Start Hack The Box (easy machines)
OverTheWire Bandit wargames
PicoCTF beginner challenges

Resources: TryHackMe | Hack The Box | OverTheWire Bandit | PicoCTF

Phase 5: Specialisation & Certification (Weeks 37+)

Goal: Earn your CompTIA Security+ certification and build a professional portfolio

Weeks 37-44: CompTIA Security+ Preparation

Exam Domains (SY0-701):

Domain 1: General Security Concepts (12%)
Domain 2: Threats, Vulnerabilities & Mitigations (22%)
Domain 3: Security Architecture (18%)
Domain 4: Security Operations (28%)
Domain 5: Security Program Management (20%)

Study Strategy:

Watch Professor Messer videos (free)
Take notes using active recall method
Complete practice exams weekly
Review incorrect answers thoroughly
Use flashcards for key terms

Resources: Professor Messer (Free) | CompTIA Security+

Weeks 45-48: Portfolio Projects

Portfolio Must-Haves:

GitHub profile with clean code
3-5 security-related projects
Documentation and READMEs
Write-ups of CTF challenges solved
Home lab documentation

Project Ideas:

Security monitoring home lab (ELK Stack)
Vulnerability scanner with Python
Packet analyser tool
Security audit automation script
Incident response playbook

Weeks 49+: Job Preparation

Job Search Activities:

Update LinkedIn with certifications
Create cybersecurity-focused CV
Practice interview questions
Network on security forums/Discord
Apply to entry-level positions

Entry-Level Roles to Target:

Security Operations Centre (SOC) Analyst
Junior Security Analyst
IT Security Specialist
Cybersecurity Technician
Security Support Analyst

Job Boards: SEEK | LinkedIn Jobs | CyberSecurity Jobsite

About CompTIA Security+ (SY0-701)

Format: 90 questions, 90 minutes
Question Types: Multiple choice + Performance-based
Passing Score: 750 out of 900
Cost: ~$400 AUD (vouchers often available for less)
Validity: 3 years (then requires renewal)

Using AI Effectively

The Core Principle

AI is most powerful when you can evaluate its output. You cannot do that without foundational knowledge.

Someone who learned with heavy AI assistance often cannot debug problems when AI fails them.

Your Goal

Solve problems without AI
Use AI to work faster
Recognize when AI is wrong

AI Usage by Phase

Period	AI Policy	Rationale
Weeks 1-8	Minimal	Building mental models; struggling builds understanding
Weeks 9-12	Limited	Can ask for concept explanations after attempting
Weeks 13-16	Moderate	Can ask for code review after writing yourself
Weeks 17+	Strategic	Use AI to accelerate, not replace, learning

Good Ways to Use AI

"I'm getting this error when I run my code: [paste error]. I've tried [what you tried]. What might be causing this?"
"Can you explain how Python dictionaries work differently from lists?"
"I wrote this function to check password strength. Can you review it and suggest improvements?"
"Give me 5 practice exercises for Python lists."

Bad Ways to Use AI

"Write me a program that does X" (without attempting first)
"Solve this exercise for me"
"Write the code" for any assignment
Copying AI code without understanding it

The Test

Before using any AI-generated code, ask yourself:

Can I explain what every line does?
Could I have written this myself (even if slower)?
Could I modify this if requirements changed?

If the answer to any is "no," you're not ready to use that code.

Weekly Study Rhythm

Recommended daily schedule for your 5-hour study sessions:

Time	Activity
0:00 - 0:30	Review previous session's notes
0:30 - 1:30	Read/watch new material
1:30 - 2:00	Break (important for retention!)
2:00 - 4:00	Hands-on coding practice
4:00 - 4:30	Break
4:30 - 5:00	Write summary notes, plan next session

Support From Your Partner

How your IT-experienced partner can help:

1. Weekly Code Review

Sit together once a week to review your code. This helps catch bad habits early and reinforces good practices.

2. Rubber Duck Debugging

Be available for you to explain problems aloud. Often, just explaining the problem helps you find the solution.

3. Quick Context Questions

Answer "why" questions that would take ages to Google. Real-world context from experience is invaluable.

4. Don't Solve Problems For You

Guide with hints, don't give answers. The struggle is where learning happens.

5. Environment Troubleshooting

Help with VM issues, network configs, and tool setup. These technical hurdles shouldn't block your learning.

Final Notes

Remember:

Progress isn't always linear. Some weeks will feel harder than others.
It's okay to repeat a week if concepts aren't sticking.
Hands-on practice is more valuable than passive watching/reading.
Building real projects (even small ones) builds real confidence.
The cybersecurity community is generally welcoming to newcomers.

You've got this!

All Resources

Phase 1 Resources

Resource	URL	Cost
CS50 (Harvard)	cs50.harvard.edu/x/	Free
CS50 YouTube	youtube.com/cs50	Free
Code.org - How Computers Work	YouTube Playlist	Free
Ubuntu Download	ubuntu.com/download	Free
VirtualBox	virtualbox.org	Free
Ubuntu CLI Tutorial	ubuntu.com/tutorials	Free
Linux Journey	linuxjourney.com	Free
NetworkChuck YouTube	youtube.com/NetworkChuck	Free
NetworkChuck CCNA Playlist	YouTube Playlist	Free
How DNS Works	howdns.works	Free
Darknet Diaries Podcast	darknetdiaries.com	Free
TryHackMe	tryhackme.com	Free tier
VS Code	code.visualstudio.com	Free

Phase 2 Resources

Resource	URL	Cost
Automate the Boring Stuff (Book)	automatetheboringstuff.com	Free online
Automate the Boring Stuff (Udemy)	Udemy Course	Paid (often free codes)
Corey Schafer Python Playlist	YouTube Playlist	Free
Python Official Documentation	docs.python.org	Free
W3Schools Python	w3schools.com/python	Free
Real Python	realpython.com	Free articles
regex101	regex101.com	Free
Python Regex HOWTO	Python Docs	Free
Google Python Crash Course	Coursera	Free to audit

Future Phase Resources

Resource	URL	Cost
TryHackMe Free Rooms List	GitHub Roadmap	Free
Professor Messer Security+	professormesser.com	Free videos
CyberSeek Career Pathway	cyberseek.org	Free

Weekly Study Rhythm

Recommended daily schedule (5-hour sessions):

Time	Activity
0:00 - 0:30	Review previous session's notes
0:30 - 1:30	Read/watch new material
1:30 - 2:00	Break (important for retention!)
2:00 - 4:00	Hands-on coding practice
4:00 - 4:30	Break
4:30 - 5:00	Write summary notes, plan next session

Support From Your Partner

How your IT-experienced partner can help:

Weekly code review - Sit together once a week to review your code
Rubber duck debugging - Be available for you to explain problems aloud
Quick context questions - Answer "why" questions that would take you ages to Google
Don't solve problems for you - Guide with hints, don't give answers
Environment troubleshooting - Help with VM issues, network configs, tool setup

Amy's Study Plan

About This Plan

Student

Background

Study Time

Goal

The Five Phases

Computer & Networking Fundamentals

Python Foundations

Python for Security

Security Fundamentals

Specialisation & Certification

Realistic Milestones

Phase 1: Computer & Networking Fundamentals

Week 1: How Computers Work + Command Line

Learning Objectives

Day 1 (5 hours)

What is Linux?

What is a Virtual Machine?

Watch First (before installing)

Day 2 (5 hours)

Day 3 (5 hours)

Commands to Master This Week

Practice Tasks

Navigation (pwd, ls, cd)

Creating Folders (mkdir)

Creating & Viewing Files (cat, echo)

Copying & Moving (cp, mv)

Deleting (rm) - Be Careful!

Final Challenge

Week 1 Milestone

Week 2: More Command Line + Text Editors

Learning Objectives

Day 1 (5 hours)

Day 2 (5 hours)

Day 3 (5 hours)

Commands to Master This Week

Week 2 Milestone

Week 3: Networking Fundamentals

Learning Objectives

Day 1 (5 hours)

Day 2 (5 hours)

Day 3 (5 hours)

Commands to Master This Week

Week 3 Milestone

Week 4: Security Mindset + Environment Setup

Learning Objectives

Day 1 (5 hours)

Day 2 (5 hours)

Day 3 (5 hours)

Week 4 Milestone

Phase 1 Complete!

Phase 2: Python Foundations

Primary Resources

Automate the Boring Stuff

Corey Schafer Python Tutorials

Week 5: Python Basics - Getting Started

Learning Objectives

Day 1 (5 hours)

Day 2 (5 hours)

Day 3 (5 hours)

Practice Programs to Write

Week 5 Milestone

Week 6: Control Flow - Making Decisions (if/else)

Learning Objectives

Day 1 (5 hours)

Day 2 (5 hours)

Day 3 (5 hours)

Practice Programs to Write

Week 6 Milestone

Week 7: Control Flow - Loops

Learning Objectives

Day 1 (5 hours)

Day 2 (5 hours)

Day 3 (5 hours)

Practice Programs to Write

Week 7 Milestone

Week 8: Functions

Learning Objectives

Day 1-2 (10 hours)