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OOTW / Chapter I - Foundation / 01. Operating Systems / Windows / 01. File System

File System

Unlike Linux, which uses a single root directory:

/

Windows commonly organizes storage using drive letters.

Examples:

C:\
D:\
E:\

Each drive contains its own directory structure.

Most Windows systems store the operating system, applications, and user data on:

C:

Why This Matters

Nearly every activity performed by an Operator involves the file system.

Examples include:

ActivityFile System Interaction
Installing softwareCreates files
Reading configurationReads files
Investigating incidentsExamines files
Hunting persistenceFinds files
Collecting evidenceAcquires files
Deploying toolsCreates files
Executing malwareReads files
Removing malwareDeletes files

Understanding the file system is therefore a prerequisite for:

  • Administration
  • Incident Response
  • Digital Forensics
  • Threat Hunting
  • Malware Analysis
  • Penetration Testing
  • Red Teaming

Hierarchical Structure

Windows organizes data as a hierarchy of directories and files.

Example:

C:\
├── Users
│   ├── Alice
│   └── Peter
│       ├── Desktop
│       └── Downloads
├── Windows
├── Program Files
├── Program Files (x86)
└── Temp

Important characteristics:

  • Every file has a path
  • Every directory can contain files
  • Every directory can contain additional directories
  • Each drive has its own root
  • Additional storage devices appear as separate drives

Paths

A path identifies the location of a file or directory.

Example:

C:\Users\Peter\Documents\report.docx

This path can be read as:

ComponentMeaning
C:Drive
UsersUser profile storage
PeterUser directory
DocumentsSubdirectory
report.docxFile

Absolute Paths

Absolute paths begin from the root of a drive.

Examples:

C:\Windows\System32\cmd.exe
C:\Users\Peter\Downloads\tool.exe
C:\Program Files\App\application.exe

Characteristics:

  • Begin with a drive letter
  • Fully identify a location
  • Valid regardless of the current directory
  • Commonly used in documentation

Relative Paths

Relative paths begin from the current directory.

Examples:

Documents\report.docx
..\Downloads\tool.exe
.\script.ps1

Special symbols:

SymbolMeaning
.Current directory
..Parent directory

Example:

Assuming your current directory is:

C:\Users\Peter\Documents

then:

..\Downloads

resolves to:

C:\Users\Peter\Downloads

Directories and Files

Windows stores information using files and directories.

Examples:

ObjectExample
Filereport.docx
DirectoryDocuments
Logapplication.log
Scriptbackup.ps1
Configurationweb.config

Naming Conventions

Windows file names are generally:

  • Not case-sensitive
  • Descriptive
  • Associated with file extensions

Examples:

report.docx
Report.docx
REPORT.docx

These typically refer to the same file.


Hidden Files

Windows supports hidden files and directories.

Examples:

AppData
ProgramData
desktop.ini

Operators frequently inspect hidden locations because they often contain:

  • User configuration
  • Application data
  • Credentials
  • Logs
  • Persistence mechanisms

Hidden files can be viewed through:

dir /a

or

Get-ChildItem -Force

File Extensions

Windows commonly identifies file types through extensions.

Examples:

ExtensionPurpose
.exeExecutable
.dllDynamic Link Library
.ps1PowerShell Script
.batBatch Script
.txtText File
.logLog File
.zipArchive

Examples:

notepad.exe
kernel32.dll
backup.ps1

Extensions often provide clues about a file's purpose.


NTFS

The most common Windows file system is:

NTFS

NTFS provides features such as:

  • Permissions
  • Ownership
  • Compression
  • Encryption
  • Journaling

Most modern Windows systems use NTFS.


Ownership

Every file and directory has an owner.

Examples:

Administrator
SYSTEM
Alice

Ownership determines who controls the object and who may modify its permissions.


Permissions

Windows controls access through permissions.

Common examples:

  • Read
  • Write
  • Modify
  • Full Control

Permissions determine who can access files and what actions they may perform.

Example:

PS C:\Users\PC> icacls.exe C:\Windows
C:\Windows NT SERVICE\TrustedInstaller:(F)
           NT SERVICE\TrustedInstaller:(CI)(IO)(F)
           NT AUTHORITY\SYSTEM:(M)
           NT AUTHORITY\SYSTEM:(OI)(CI)(IO)(F)
           BUILTIN\Administrators:(M)
           BUILTIN\Administrators:(OI)(CI)(IO)(F)
           BUILTIN\Users:(RX)
           BUILTIN\Users:(OI)(CI)(IO)(GR,GE)
           CREATOR OWNER:(OI)(CI)(IO)(F)
           APPLICATION PACKAGE AUTHORITY\ALL APPLICATION PACKAGES:(RX)
           APPLICATION PACKAGE AUTHORITY\ALL APPLICATION PACKAGES:(OI)(CI)(IO)(GR,GE)
           APPLICATION PACKAGE AUTHORITY\ALL RESTRICTED APPLICATION PACKAGES:(RX)
           APPLICATION PACKAGE AUTHORITY\ALL RESTRICTED APPLICATION PACKAGES:(OI)(CI)(IO)(GR,GE)

Permission concepts will be explored in greater depth later within the Privileges & Integrity Levels section.


Alternate Data Streams

NTFS supports additional hidden streams attached to files.

Example:

echo secret > report.txt:hidden

The file:

report.txt

appears normal.

However, an additional stream named:

hidden

also exists.

Alternate Data Streams can be used legitimately but have historically appeared in malware and persistence techniques.

Example:

PS C:\Users\PC\Desktop\Demo> Set-Content -Path .\report.txt -Stream hidden -Value "secret"
PS C:\Users\PC\Desktop\Demo> ls

    Directory: C:\Users\PC\Desktop\Demo

Mode                 LastWriteTime         Length Name
----                 -------------         ------ ----
-a---           6/18/2026  4:49 PM              0 report.txt

PS C:\Users\PC\Desktop\Demo> Get-Item .\report.txt -Stream *

PSPath        : Microsoft.PowerShell.Core\FileSystem::C:\Users\PC\Desktop\Demo\report.txt::$DATA
PSParentPath  : Microsoft.PowerShell.Core\FileSystem::C:\Users\PC\Desktop\Demo
PSChildName   : report.txt::$DATA
PSDrive       : C
PSProvider    : Microsoft.PowerShell.Core\FileSystem
PSIsContainer : False
FileName      : C:\Users\PC\Desktop\Demo\report.txt
Stream        : :$DATA
Length        : 0

PSPath        : Microsoft.PowerShell.Core\FileSystem::C:\Users\PC\Desktop\Demo\report.txt:hidden
PSParentPath  : Microsoft.PowerShell.Core\FileSystem::C:\Users\PC\Desktop\Demo
PSChildName   : report.txt:hidden
PSDrive       : C
PSProvider    : Microsoft.PowerShell.Core\FileSystem
PSIsContainer : False
FileName      : C:\Users\PC\Desktop\Demo\report.txt
Stream        : hidden
Length        : 8

Drive Letters

Windows commonly exposes storage through drive letters.

Examples:

C:
D:
E:

These may represent:

  • Internal drives
  • External drives
  • USB devices
  • Optical media
  • Network mappings

Operators frequently enumerate available drives during investigations.


Operator Perspective

When approaching an unfamiliar Windows system, Operators typically ask:

Structure

  • What drives exist?
  • What directories exist?
  • What storage is attached?

Files

  • What files are present?
  • What files were recently modified?
  • What files appear unusual?

Ownership

  • Who owns important files?
  • Are permissions overly permissive?

Persistence

  • What files execute automatically?
  • What hidden files exist?

Evidence

  • What exists within Downloads?
  • What exists within Temp?
  • Where are logs stored?
  • Where are application files stored?

Understanding the file system provides the foundation for answering all of these questions.


Key Takeaways

  • Windows organizes data using drives, directories, and files.
  • Files are identified using paths.
  • Paths may be absolute or relative.
  • Most systems use the C: drive for the operating system.
  • Files and directories have owners.
  • Files and directories have permissions.
  • Windows supports hidden files and directories.
  • NTFS provides permissions, ownership, encryption, and journaling.
  • Alternate Data Streams can store hidden data.
  • Understanding the file system is foundational for both offensive and defensive operations.

The next lesson explores Users & Groups and how Windows manages identities and access control.