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Build a Vulnerable IIS SharePoint Lab with Fluent Bit: Complete Deployment Guide

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Ecosystem Fit​

This page mirrors the original Medium article into the 1200km.com Docusaurus ecosystem. The original article flow, images, screenshots, infographics, and technical blocks are preserved from the export.

A full step-by-step guide with all scripts to deploy a vulnerable SharePoint-style site on Windows IIS and ship its logs with Fluent Bit — from scratch.​

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Introduction​

Most people learn IIS and “SharePoint” pentesting the hard way: in production, under pressure, with incomplete logs, and with zero room to break things. That’s backwards.

If you want to become effective at web pentesting (or detection engineering) you need arepeatable labthat you can reset, attack, and observe — over and over — until patterns become instinct. Not “a random vulnerable VM,” but a realistic stack that mirrors what you’ll actually meet in enterprise environments:

  • Windows Server + IIS(classic target surface)

  • SharePoint-style app patterns(auth-less pages, legacy ASP.NET, messy inputs)

  • Attack scenarios that generate teachable telemetry(XSS, traversal, SQLi-like payloads)

  • Proper logging coverageso every request leaves evidence: access logs, kernel-level rejects, deep diagnostics, and Windows events

  • Centralized shippingso you train thereal workflow: attack → logs → search/hunt → detection rules

That’s exactly what this guide gives you.

You’ll build afully automated vulnerable IIS lab(Windows Server 2012 R2 in Vagrant) with a purposely insecure “SharePoint-style” ASP.NET site, and you’ll instrument it withFluent Bit as a Windows serviceto forwardIIS W3C,HTTPERR,Failed Request Tracing,ULS-style app logs, andWindows Event Logsto an HTTP backend (like XPLG or any listener).

Why this matters for pentest training:

  • You don’t just “get a payload to work”— you learn what success and failurelook like in logs.

  • You can practicereal reporting: reproduce, capture evidence, explain impact, map telemetry.

  • Blue team? Same lab becomes your detection range: write queries, build alerts, validate them against known traffic.

  • You can reset fast and iterate:infrastructure-as-labbeats “pet VMs” every time.

The goal is simple:turn pentesting practice into an engineering loop— controlled exploits, consistent telemetry, and repeatable experiments — so you build skill that transfers directly to real environments.

What You’ll Build​

  • Windows Server 2012 R2 VM(Vagrant + libvirt/VirtualBox)

  • IISwith W3C logging, Failed Request Tracing

  • Vulnerable SharePoint app— XSS, path traversal, SQLi simulation (all requests logged)

  • Fluent Bit— Windows service collecting IIS + Windows Event logs, shipping to HTTP backend

Table of Contents​

  • Introduction

  • Prerequisites

  • Project Structure

  • 1. Vagrantfile

  • 2. Provisioning Script: enable-rdp.ps1

  • 3. Provisioning Script: install-iis.ps1

  • 4. Provisioning Script: install-sharepoint.ps1

  • 5. Provisioning Script: install-fluent-bit.ps1

  • 6. Vulnerable SharePoint App

  • 7. IIS Log Types: Access vs Error

  • 8. Fluent Bit Config: fluent-bit.conf

  • 9. Fluent Bit Parsers: parsers.conf

  • Deployment Steps

Prerequisites​

  • Vagrant2.2+

  • libvirt+vagrant-libvirt(or VirtualBox)

  • FreeRDP(freerdp2-x11)

sudo apt install vagrant libvirt-daemon-
system
 libvirt-clients qemu-kvm vagrant-libvirt freerdp2-x11
sudo usermod -aG libvirt $USER
# Log out and back in

Project Structure​

Create the following layout:

Windows_IIS/
├── Vagrantfile
├── fluent-bit/
│   ├── fluent-bit.conf
│   └── parsers.conf
├── vulnerable-sharepoint/
│   ├── 
default
.aspx
│   ├── search.aspx
│   ├── documents.aspx
│   ├── api.aspx
│   └── Web.config
└── provisioning/
    ├── enable-rdp.ps1
    ├── install-iis.ps1
    ├── install-sharepoint.ps1
    └── install-fluent-bit.ps1

1. Vagrantfile​

# Windows IIS + SharePoint Foundation VM (vulnerable, for logging training)
# Uses pre-built Windows Server 2012 R2 box. For custom build from ISO, see docs/PACKER_FROM_ISO.md
# ISO reference: /home/andrey/DC_simulator/iso/Windows_Server_2012_R2_Evaluation.iso
Vagrant.configure(
"2"
) 
do
 |config|
  config.vm.box = 
"jborean93/WindowsServer2012R2"
  config.vm.box_version = 
"1.1.0"
  config.vm.guest = :windows
  config.vm.communicator = 
"winrm"
  config.winrm.username = 
"vagrant"
  config.winrm.password = 
"vagrant"
  config.vm.provider 
"virtualbox"
 
do
 |vb|
    vb.name = 
"windows-iis-sharepoint"
    vb.memory = 4096
    vb.cpus = 2
    vb.customize [
"modifyvm"
, :
id
, 
"--vram"
, 
"64"
]
  end
  config.vm.provider 
"libvirt"
 
do
 |lv|
    lv.memory = 4096
    lv.cpus = 2
    lv.management_network_name = 
"default"
  end
  
# Private network: VM gets 192.168.56.10, host is 192.168.56.1 (VirtualBox) or virbr0 (libvirt)
  
# Fluent Bit will send to host (log-listener, XPLG) at this IP
  config.vm.network 
"private_network"
, ip: 
"192.168.56.10"
  
# Upload fluent-bit config (avoids synced folder issues)
  config.vm.provision 
"file"
, 
source
: 
"fluent-bit/fluent-bit.conf"
, destination: 
"C:/tmp/fluent-bit.conf"
  config.vm.provision 
"file"
, 
source
: 
"fluent-bit/parsers.conf"
, destination: 
"C:/tmp/parsers.conf"
  
# Upload vulnerable SharePoint app
  config.vm.provision 
"file"
, 
source
: 
"vulnerable-sharepoint/default.aspx"
, destination: 
"C:/tmp/vulnerable-sharepoint/default.aspx"
  config.vm.provision 
"file"
, 
source
: 
"vulnerable-sharepoint/search.aspx"
, destination: 
"C:/tmp/vulnerable-sharepoint/search.aspx"
  config.vm.provision 
"file"
, 
source
: 
"vulnerable-sharepoint/documents.aspx"
, destination: 
"C:/tmp/vulnerable-sharepoint/documents.aspx"
  config.vm.provision 
"file"
, 
source
: 
"vulnerable-sharepoint/api.aspx"
, destination: 
"C:/tmp/vulnerable-sharepoint/api.aspx"
  config.vm.provision 
"file"
, 
source
: 
"vulnerable-sharepoint/Web.config"
, destination: 
"C:/tmp/vulnerable-sharepoint/Web.config"
  
# Provision: enable RDP first, then IIS, SharePoint (with vulnerable app), Fluent Bit
  config.vm.provision 
"shell"
, path: 
"provisioning/enable-rdp.ps1"
, privileged: 
false
  config.vm.provision 
"shell"
, path: 
"provisioning/install-iis.ps1"
, privileged: 
false
  config.vm.provision 
"shell"
, path: 
"provisioning/install-sharepoint.ps1"
, privileged: 
true
  config.vm.provision 
"shell"
, path: 
"provisioning/install-fluent-bit.ps1"
, privileged: 
false
, args: [
"C:/tmp"
]
end

2. Provisioning Script: enable-rdp.ps1​

enable-rdp.
ps1
# Enable RDP and open firewall for Remote Desktop
$ErrorActionPreference = 
"Stop"
Write-Host 
"Enabling Remote Desktop..."
Set
-ItemProperty -Path 
"HKLM:\System\CurrentControlSet\Control\Terminal Server"
 -Name 
"fDenyTSConnections"
 -Value 
0
 -Force
Set
-ItemProperty -Path 
"HKLM:\System\CurrentControlSet\Control\Terminal Server\WinStations\RDP-Tcp"
 -Name 
"UserAuthentication"
 -Value 
0
 -Force
Write-Host 
"Opening firewall for RDP..."
Enable-NetFirewallRule -DisplayGroup 
"Remote Desktop"
New-NetFirewallRule -DisplayName 
"RDP"
 -Direction Inbound -Protocol TCP -LocalPort 
3389
 -Action Allow -ErrorAction SilentlyContinue
Write-Host 
"RDP enabled. Restart required for some settings - or connect now."
Restart-Service TermService -Force -ErrorAction SilentlyContinue

3. Provisioning Script: install-iis.ps1​

install-iis.
ps1
# Install IIS with common features (vulnerable config for training)
$ErrorActionPreference = "Stop"
Write-Host "Installing IIS and Web features..."
Install-WindowsFeature -Name Web-Server -IncludeManagementTools
Install-WindowsFeature -Name Web-ASP-Net45
Install-WindowsFeature -Name Web-Net-Ext45
Install-WindowsFeature -Name Web-ISAPI-Ext
Install-WindowsFeature -Name Web-ISAPI-Filter
Install-WindowsFeature -Name Web-Log-Libraries
Install-WindowsFeature -Name Web-Request-Monitor
Install-WindowsFeature -Name Web-Http-Tracing
Install-WindowsFeature -Name Web-Stat-Compression
Install-WindowsFeature -Name Web-Dyn-Compression
Import-Module WebAdministration
Set-ItemProperty "IIS:\Sites\Default Web Site" -Name logFile.logFormat -Value "W3C"
Set-ItemProperty "IIS:\Sites\Default Web Site" -Name logFile.logExtFileFlags -Value "Date,Time,ClientIP,UserName,ServerIP,Method,UriStem,UriQuery,HttpStatus,Win32Status,TimeTaken,ServerPort,UserAgent,Referer"
Set-ItemProperty "IIS:\Sites\Default Web Site" -Name logFile.directory -Value "C:\inetpub\logs\LogFiles"
$content = @"
<!DOCTYPE 
html
>
<
html
>
<
head
>
<
title
>
SharePoint-style Site
</
title
>
</
head
>
<
body
>
<
h1
>
Simple SharePoint-style Landing
</
h1
>
<
p
>
This is a minimal IIS site for logging training. Vulnerable configuration.
</
p
>
<
p
>
Time: $(Get-Date)
</
p
>
</
body
>
</
html
>
"@
$content | Out-File -FilePath "C:\inetpub\wwwroot\default.aspx" -Encoding UTF8
New-Item -ItemType Directory -Force -Path "C:\inetpub\logs\LogFiles" | Out-Null
New-Item -ItemType Directory -Force -Path "C:\inetpub\logs\FailedReqLogFiles" | Out-Null
Write-Host "IIS installation complete."

4. Provisioning Script: install-sharepoint.ps1​

install-sharepoint.
ps1
# Vulnerable SharePoint-style setup - precompiles to avoid ASP.NET temp folder permission issues
$ErrorActionPreference
 = 
"Stop"
Import-Module WebAdministration
if
 (-
not
 (Test-Path 
"IIS:\AppPools\SharePointAppPool"
)) {
    New-WebAppPool -Name 
"SharePointAppPool"
    Set-ItemProperty 
"IIS:\AppPools\SharePointAppPool"
 -Name 
"managedRuntimeVersion"
 -Value 
"v4.0"
}
$sitePath
 = 
"C:\inetpub\wwwroot\SharePointSite"
$stagingPath
 = 
"C:\inetpub\wwwroot\SharePointStaging"
$vulnSource
 = 
$null
if
 (Test-Path 
"C:\vagrant\vulnerable-sharepoint\default.aspx"
) { 
$vulnSource
 = 
"C:\vagrant\vulnerable-sharepoint"
 }
elseif
 (Test-Path 
"C:\tmp\vulnerable-sharepoint\default.aspx"
) { 
$vulnSource
 = 
"C:\tmp\vulnerable-sharepoint"
 }
if
 (
$vulnSource
) {
    Write-Host 
"Deploying and precompiling vulnerable SharePoint app..."
    
if
 (Test-Path 
$stagingPath
) { Remove-Item -Path 
$stagingPath
 -Recurse -Force }
    New-Item -ItemType 
Directory
 -Force -Path 
$stagingPath
 | Out-Null
    Copy-Item -Path 
"
$vulnSource
\*"
 -Destination 
$stagingPath
 -Recurse -Force
    
if
 (Test-Path 
$sitePath
) { Remove-Item -Path 
"
$sitePath
\*"
 -Recurse -Force }
    New-Item -ItemType 
Directory
 -Force -Path 
$sitePath
 | Out-Null
    & 
"
$env
:SystemRoot\Microsoft.NET\Framework64\v4.0.30319\aspnet_compiler.exe"
 -p 
$stagingPath
 -v / -fixednames 
$sitePath
    Remove-Item -Path 
$stagingPath
 -Recurse -Force -ErrorAction SilentlyContinue
    Write-Host 
"Vulnerable app precompiled and deployed."
} 
else
 {
    Write-Host 
"Vulnerable app not found, creating placeholder..."
    
$pageContent
 = @
"
<!DOCTYPE html>
<html><head><title>SharePoint</title></head>
<body><h1>SharePoint-style Site</h1><p>Placeholder.</p></body>
</html>
"
@
    
$pageContent
 | Out-File -FilePath 
"
$sitePath
\default.aspx"
 -Encoding UTF8
}
$acl
 = Get-Acl 
$sitePath
$rule
 = New-Object System.Security.AccessControl.
FileSystemAccessRule
(
"IIS AppPool\SharePointAppPool"
, 
"Read"
, 
"ContainerInherit,ObjectInherit"
, 
"None"
, 
"Allow"
)
$acl
.
SetAccessRule
(
$rule
)
Set-Acl 
$sitePath
 
$acl
$siteName
 = 
"SharePointSite"
if
 (-
not
 (Test-Path 
"IIS:\Sites\$siteName"
)) {
    New-Website -Name 
$siteName
 -PhysicalPath 
$sitePath
 -ApplicationPool 
"SharePointAppPool"
 -Port 
8080
    Write-Host 
"SharePoint site created on port 8080."
} 
else
 {
    Set-ItemProperty 
"IIS:\Sites\$siteName"
 -Name physicalPath -Value 
$sitePath
}
$ulsPath
 = 
"C:\Program Files\Common Files\Microsoft Shared\Web Server Extensions\15\LOGS"
New-Item -ItemType 
Directory
 -Force -Path 
$ulsPath
 | Out-Null
"# SharePoint ULS-style log - $(Get-Date)"
 | Out-File 
"
$ulsPath
\uls.log"
 -Encoding UTF8
Write-Host 
"SharePoint-style setup complete."

5. Provisioning Script: install-fluent-bit.ps1​

# Install Fluent Bit on Windows - downloads from packages.fluentbit.io, installs as service
$ErrorActionPreference
 = 
"Stop"
[Net.ServicePointManager]::
SecurityProtocol
 = [Net.SecurityProtocolType]::
Tls12
$fluentBitVersion
 = 
"4.2.2"
$fluentBitUrl
 = 
"https://packages.fluentbit.io/windows/fluent-bit-
$fluentBitVersion
-win64.zip"
$installDir
 = 
"C:\fluent-bit"
$configDir
 = 
"
$installDir
\conf"
Write-Host 
"Installing Fluent Bit 
$fluentBitVersion
..."
New-Item -ItemType 
Directory
 -Force -Path 
$installDir
 | Out-Null
New-Item -ItemType 
Directory
 -Force -Path 
"
$installDir
\data"
 | Out-Null
New-Item -ItemType 
Directory
 -Force -Path 
"
$installDir
\data\chunks"
 | Out-Null
New-Item -ItemType 
Directory
 -Force -Path 
$configDir
 | Out-Null
$zipPath
 = 
"
$env
:TEMP\fluent-bit-
$fluentBitVersion
-win64.zip"
if
 (-
not
 (Test-Path 
$zipPath
)) {
    Write-Host 
"Downloading Fluent Bit..."
    Invoke-WebRequest -Uri 
$fluentBitUrl
 -OutFile 
$zipPath
 -UseBasicParsing
}
$svc
 = Get-Service -Name 
"fluent-bit"
 -ErrorAction SilentlyContinue
if
 (
$svc
 -
and
 
$svc
.Status -eq 
"Running"
) {
    Stop-Service fluent-bit -Force
    Start-Sleep -Seconds 
2
}
Write-Host 
"Extracting Fluent Bit..."
$extractDir
 = 
"
$env
:TEMP\fluent-bit-extract"
if
 (Test-Path 
$extractDir
) { Remove-Item -Path 
$extractDir
 -Recurse -Force }
Add-Type -AssemblyName System.IO.Compression.FileSystem
[System.IO.Compression.ZipFile]::
ExtractToDirectory
(
$zipPath
, 
$extractDir
)
$extractedDir
 = Get-ChildItem -Path 
$extractDir
 -
Directory
 | Where-Object { 
$_
.Name -like 
"fluent-bit*"
 } | Select-Object -First 
1
if
 (
$extractedDir
) {
    Get-ChildItem -Path 
$extractedDir
.FullName | ForEach-Object {
        
$dest
 = Join-Path 
$installDir
 
$_
.Name
        
if
 (Test-Path 
$dest
) { Remove-Item -Path 
$dest
 -Recurse -Force }
        Move-Item -Path 
$_
.FullName -Destination 
$installDir
 -Force
    }
    Remove-Item -Path 
$extractDir
 -Recurse -Force -ErrorAction SilentlyContinue
}
$configSource
 = 
$args
[
0
]
if
 (-not 
$configSource
) { 
$configSource
 = 
"C:\tmp"
 }
if
 (Test-
Path
 (Join-Path 
$configSource
 
"fluent-bit.conf"
)) {
    Copy-
Item
 (Join-Path 
$configSource
 
"fluent-bit.conf"
) -Destination 
$configDir
 -Force
    Copy-
Item
 (Join-Path 
$configSource
 
"parsers.conf"
) -Destination 
$configDir
 -Force
    Write-Host 
"Config copied from 
$configSource
"
} 
else
 {
    Write-Host 
"ERROR: fluent-bit config not found"
    
exit
 
1
}
$fluentBitExe
 = Join-Path 
$installDir
 
"bin\fluent-bit.exe"
$configPath
 = Join-Path 
$configDir
 
"fluent-bit.conf"
if
 (Test-Path 
$fluentBitExe
) {
    
$binPath
 = 
"
$fluentBitExe
 -c 
$configPath
"
    
$existing
 = Get-Service -Name 
"fluent-bit"
 -ErrorAction SilentlyContinue
    
if
 (
$existing
) {
        sc.exe delete fluent-bit
        Start-Sleep -Seconds 
2
    }
    sc.exe create fluent-bit binpath= 
$binPath
 start= auto
    Write-Host 
"Fluent Bit installed as Windows service."
    Start-Service fluent-bit -ErrorAction SilentlyContinue
} 
else
 {
    Write-Host 
"WARNING: fluent-bit.exe not found."
}
Write-Host 
"Fluent Bit installation complete."

6. Vulnerable SharePoint App​

default.aspx​

default
.aspx
<%@ Page Language="C#" %>
<!DOCTYPE 
html
>
<
html
>
<
head
>
<
title
>
Vulnerable SharePoint - Logging Training
</
title
>
</
head
>
<
body
>
<
h1
>
Vulnerable SharePoint Site
</
h1
>
<
p
>
Intentionally vulnerable for security and logging training. All activity is logged.
</
p
>
<
ul
>
<
li
>
<
a
 
href
=
"default.aspx"
>
Home
</
a
>
</
li
>
<
li
>
<
a
 
href
=
"search.aspx"
>
Search (XSS)
</
a
>
</
li
>
<
li
>
<
a
 
href
=
"documents.aspx"
>
Documents (Path Traversal)
</
a
>
</
li
>
<
li
>
<
a
 
href
=
"api.aspx"
>
API (SQLi simulation)
</
a
>
</
li
>
</
ul
>
<
p
>
Request at: <%= DateTime.Now %>
</
p
>
</
body
>
</
html
>

search.aspx (Reflected XSS)​

search.
aspx
<%@ Page Language="C#" %>
<!DOCTYPE 
html
>
<
html
>
<
head
>
<
title
>
Search - Vulnerable SharePoint
</
title
>
</
head
>
<
body
>
<
h1
>
Document Search
</
h1
>
<
form
 
method
=
"GET"
 
action
=
"search.aspx"
>
  
<
input
 
type
=
"text"
 
name
=
"q"
 
value
=
"<%= Request.QueryString["
q
"] ?? "" %>
" />
  
<
input
 
type
=
"submit"
 
value
=
"Search"
 />
</
form
>
<% if (!string.IsNullOrEmpty(Request.QueryString["q"])) { %>
  
<
p
>
Results for: <%= Request.QueryString["q"] %>
</
p
>
  
<
p
>
<
em
>
Vulnerable: reflected XSS in search - payload appears in response
</
em
>
</
p
>
<% } %>
<
p
>
<
a
 
href
=
"default.aspx"
>
Back
</
a
>
</
p
>
</
body
>
</
html
>

documents.aspx (Path Traversal)​

documents.
aspx
<%@ Page Language="C#" %>
<!DOCTYPE 
html
>
<
html
>
<
head
>
<
title
>
Documents - Vulnerable SharePoint
</
title
>
</
head
>
<
body
>
<
h1
>
Document Library
</
h1
>
<
form
 
method
=
"GET"
 
action
=
"documents.aspx"
>
  
<
label
>
File: 
<
input
 
type
=
"text"
 
name
=
"file"
 
value
=
"<%= Request.QueryString["
file
"] ?? "
report.pdf
" %>
" />
</
label
>
  
<
input
 
type
=
"submit"
 
value
=
"Open"
 />
</
form
>
<% 
string file = Request.QueryString["file"];
if (!string.IsNullOrEmpty(file)) {
  bool looksSuspicious = file.Contains("..") || file.Contains(":");
  Response.Write("
<
p
>
Requested file: " + Server.HtmlEncode(file) + "
</
p
>
");
  if (looksSuspicious) {
    Response.Write("
<
p
>
<
strong
>
Path traversal attempt detected - logged!
</
strong
>
</
p
>
");
  }
  Response.Write("
<
p
>
<
em
>
Vulnerable: path traversal attempts are logged for analysis
</
em
>
</
p
>
");
}
%>
<
p
>
<
a
 
href
=
"default.aspx"
>
Back
</
a
>
</
p
>
</
body
>
</
html
>

api.aspx (SQLi Simulation)​

api.
aspx
<%@ Page Language="C#" %>
<%@ Import Namespace="System.Data" %>
<!DOCTYPE 
html
>
<
html
>
<
head
>
<
title
>
API - Vulnerable SharePoint
</
title
>
</
head
>
<
body
>
<
h1
>
REST API (SQLi simulation)
</
h1
>
<
form
 
method
=
"GET"
 
action
=
"api.aspx"
>
  
<
label
>
User ID: 
<
input
 
type
=
"text"
 
name
=
"id"
 
value
=
"<%= Request.QueryString["
id
"] ?? "
1
" %>
" />
</
label
>
  
<
input
 
type
=
"submit"
 
value
=
"Query"
 />
</
form
>
<% 
string id = Request.QueryString["id"];
if (!string.IsNullOrEmpty(id)) {
  string fakeQuery = "SELECT * FROM users WHERE id='" + id + "'";
  Response.Write("
<
p
>
Simulated query (logged): " + Server.HtmlEncode(fakeQuery) + "
</
p
>
");
  Response.Write("
<
p
>
<
em
>
Vulnerable: SQL injection - try id=1' OR '1'='1
</
em
>
</
p
>
");
}
%>
<
p
>
<
a
 
href
=
"default.aspx"
>
Back
</
a
>
</
p
>
</
body
>
</
html
>

Web.config​

Web.
config
<?xml version=
"1.0"
 encoding=
"utf-8"
?>
<
configuration
>
  
<
system.web
>
    
<
compilation
 
debug
=
"true"
 
targetFramework
=
"4.5"
 
tempDirectory
=
"C:\inetpub\temp\ASP.NET"
 />
    
<
httpRuntime
 
targetFramework
=
"4.5"
 />
  
</
system.web
>
</
configuration
>

7. IIS Log Types: Access vs Error​

This topic explains each log type collected by Fluent Bit and whether it is anaccess log(successful requests) or anerror log(failures, rejections, diagnostics).

Access Logs​

IIS W3C Extended Log (iis.w3c)

**Type:**Access log Path:C:\inetpub\logs\LogFiles\W3SVC*/*.log **Format:**W3C Extended Log Format (space-separated)

Recordsevery HTTP requestthat reaches IIS, whether it succeeds or fails from the application’s perspective. Each line typically includes:

**Use case:**Traffic analysis, security auditing, performance, debugging. You see all requests, including 4xx/5xx responses.

**Note:**W3C logs include both successful (2xx) and failed (4xx, 5xx) requests. “Access” here means “request log,” not “success-only.”

Error Logs​

HTTPERR (iis.httperr)

**Type:**Error log Path:C:\Windows\System32\LogFiles\HTTPERR\*.log **Format:**Space-separated

Records events whereHTTP.sys(kernel-mode HTTP driver) rejects or fails requestsbeforethey reach IIS. Typical cases:

  • Connection timeouts

  • Rejected connections (e.g. too many)

  • Invalid requests

  • SSL/TLS handshake failures

  • Request header/body issues

Example events:

  • Timer_ConnectionIdle— client idle timeout

  • Timer_MinBytesPerSecond— slow client

  • Rejected— connection rejected

  • SSL handshake— TLS errors

**Use case:**Diagnosing connection and low-level HTTP issues that never reach the application.

Failed Request Tracing (iis.freb)​

**Type:**Error / diagnostic log Path:C:\inetpub\logs\FailedReqLogFiles\*\*.xml **Format:**XML

Generated whenFailed Request Tracingis enabled for a site. Contains detailed diagnostics for requests that meet failure rules (e.g. status 500, slow requests).

Contents:

  • Request details

  • Module trace (which module failed)

  • Stack traces

  • Timing

**Use case:**Deep troubleshooting of specific failing requests. Must be enabled per-site in IIS.

Application Logs​

SharePoint ULS (sharepoint.uls)

**Type:**Application log Path:C:\Program Files\Common Files\Microsoft Shared\Web Server Extensions\15\LOGS\*.log **Format:**Tab-separated

SharePoint Unified Logging Service logs. Contains application-level events, errors, and traces from SharePoint.

**Use case:**SharePoint-specific debugging and monitoring. Only present if SharePoint (or a similar structure) is installed.

Windows Event Log — Application (windows.application)​

**Type:**System / application log **Source:**Windows Event Log API **Channel:**Application

System and application events from the Application channel, including IIS and ASP.NET.

**Use case:**Service starts/stops, application crashes, and other system-level events.

Summary: Access vs Error​

Access logs= what was requested (W3C). Error logs= what failed and why (HTTPERR, FREB, ULS, Event Log).

8. Fluent Bit Config: fluent-bit.conf​

fluent-bit.
conf
# Fluent Bit for Windows IIS - raw collection, NO log modifications
# Outputs logs as-is from each source. Adjust Host/Port in [OUTPUT] for your backend.
[
SERVICE
]
    
Flush
         
2
    
Grace
         
30
    
Log_Level
     
info
    
Parsers_File
  
parsers.conf
    
storage.path
  
C:/fluent-bit/data/chunks
    
storage.sync
  
normal
# --- ACCESS LOGS ---
# IIS W3C Extended Log (access log)
# Path: C:\inetpub\logs\LogFiles\W3SVC*/*.log
# Tag: iis.w3c
[
INPUT
]
    
Name
              
tail
    
Tag
               
iis.w3c
    
Path
              
C:/inetpub/logs/LogFiles/W3SVC*/*.log
    
Parser
            
iis_w3c
    
Path_Key
          
source_path
    
DB
                
C:/fluent-bit/data/flb_iis.db
    
Mem_Buf_Limit
     
5MB
    
Refresh_Interval
  
10
    
Ignore_Older
      
1h
    
Read_from_Head
    
On
# --- ERROR LOGS ---
# HTTPERR (HTTP.sys error log)
# Path: C:\Windows\System32\LogFiles\HTTPERR\*.log
# Tag: iis.httperr
[
INPUT
]
    
Name
              
tail
    
Tag
               
iis.httperr
    
Path
              
C:/Windows/System32/LogFiles/HTTPERR/*.log
    
Parser
            
iis_httperr
    
DB
                
C:/fluent-bit/data/flb_httperr.db
    
Mem_Buf_Limit
     
2MB
    
Refresh_Interval
  
10
    
Ignore_Older
      
1h
    
Read_from_Head
    
On
# Failed Request Tracing (diagnostic XML)
# Path: C:\inetpub\logs\FailedReqLogFiles\*\*.xml
# Tag: iis.freb
[
INPUT
]
    
Name
              
tail
    
Tag
               
iis.freb
    
Path
              
C:/inetpub/logs/FailedReqLogFiles/*/*.xml
    
Parser
            
iis_freb
    
DB
                
C:/fluent-bit/data/flb_freb.db
    
Mem_Buf_Limit
     
2MB
    
Refresh_Interval
  
10
    
Ignore_Older
      
1h
    
Read_from_Head
    
On
# --- SHAREPOINT / APPLICATION ---
# SharePoint ULS (Unified Logging Service)
# Path: ...\Web Server Extensions\15\LOGS\*.log
# Tag: sharepoint.uls
[
INPUT
]
    
Name
              
tail
    
Tag
               
sharepoint.uls
    
Path
              
C:/Program
 
Files/Common
 
Files/Microsoft
 
Shared/Web
 
Server
 
Extensions/15/LOGS/*.log
    
Parser
            
sharepoint_uls
    
DB
                
C:/fluent-bit/data/flb_uls.db
    
Mem_Buf_Limit
     
5MB
    
Refresh_Interval
  
10
    
Ignore_Older
      
1h
    
Read_from_Head
    
On
    
Path_Key
          
source_path
# Windows Event Log - Application channel
# Tag: windows.application
[
INPUT
]
    
Name
              
winlog
    
Tag
               
windows.application
    
Channels
         
Application
    
Interval_Sec
      
5
# --- FILTERS: separate logs by type for XPLG (cluster_name->source->host) ---
[
FILTER
]
    
Name
    
modify
    
Match
   
iis.w3c
    
Add
     
cluster_name
 
windows-iis-vm
    
Add
     
source
       
iis_w3c
    
Add
     
log_type
     
access
[
FILTER
]
    
Name
    
modify
    
Match
   
iis.httperr
    
Add
     
cluster_name
 
windows-iis-vm
    
Add
     
source
       
iis_httperr
    
Add
     
log_type
     
error
[
FILTER
]
    
Name
    
modify
    
Match
   
iis.freb
    
Add
     
cluster_name
 
windows-iis-vm
    
Add
     
source
       
iis_freb
    
Add
     
log_type
     
error
[
FILTER
]
    
Name
    
modify
    
Match
   
sharepoint.uls
    
Add
     
cluster_name
 
windows-iis-vm
    
Add
     
source
       
sharepoint_uls
    
Add
     
log_type
     
application
[
FILTER
]
    
Name
    
modify
    
Match
   
windows.application
    
Add
     
cluster_name
 
windows-iis-vm
    
Add
     
source
       
windows_event
    
Add
     
log_type
     
system
# Normalize message field (XPLG expects message for display)
[
FILTER
]
    
Name
    
modify
    
Match
   
iis.*
    
Rename
  
log
 
message
[
FILTER
]
    
Name
    
modify
    
Match
   
sharepoint.*
    
Rename
  
log
 
message
[
FILTER
]
    
Name
    
modify
    
Match
   
windows.*
    
Rename
  
Message
 
message
# Ensure "log" field for XPLG (many collectors use "log" as primary display)
[
FILTER
]
    
Name
    
modify
    
Match
   
*
    
Copy
    
message
 
log
# --- OUTPUT ---
[
OUTPUT
]
    
Name
            
http
    
Match
           
*
    
Host
            
192.168
.56
.1
    
Port
            
8081
    
URI
             
/ingest
    
Format
          
json_stream
    
Json_date_key
   
timestamp
    
Json_date_format
 
iso8601
[
OUTPUT
]
    
Name
                
http
    
Match
               
*
    
Host
                
192.168
.56
.1
    
Port
                
30303
    
URI
                 
/logeye/api/logger.jsp?token=b757c1af-2664-4c90-adf5-1a58fa1bf2ab
    
Format
              
json
    
Json_date_key
       
time
    
Json_date_format
    
iso8601
    
Retry_Limit
         
5
    
Header
              
X-Xpolog-Sender
 
fluent-bit-windows-iis
Note:
 Change 
Host
 and 
Port
 in 
[OUTPUT]
 to your log backend. 
192.168.56.1
 is the host on the Vagrant private network.

9. Fluent Bit Parsers: parsers.conf​

parsers.
conf
[PARSER]
    Name        iis_w3c
    Format      regex
    Regex       ^(?<date>\d
{4}
-\d
{2}
-\d
{2}
) (?<
time
>\d
{2}
:\d
{2}
:\d
{2}
) (?<
log
>.*)$
    Time_Key    
time
    Time_Format %H:%M:%S
    Time_Keep   On
[PARSER]
    Name        iis_w3c_header
    Format      regex
    Regex       ^
#(?<log>.*)$
    Time_Keep   Off
[PARSER]
    Name        iis_httperr
    Format      regex
    Regex       ^(?<date>\d
{4}
-\d
{2}
-\d
{2}
) (?<
time
>\d
{2}
:\d
{2}
:\d
{2}\.\d
+) (?<c_ip>[^ ]+) (?<cs_method>[^ ]+) (?<cs_uri_stem>[^ ]+) (?<sc_status>[^ ]+) (?<s_port>[^ ]+) (?<cs_referer>[^ ]+) (?<cs_user_agent>[^ ]+)
    Time_Key    
time
    Time_Format %H:%M:%S
    Time_Keep   On
[PARSER]
    Name        iis_freb
    Format      regex
    Regex       ^(?<
log
>.*)$
    Time_Keep   Off
[PARSER]
    Name        sharepoint_uls
    Format      regex
    Regex       ^(?<timestamp>\d
{2}
/\d
{2}
/\d
{4}
 \d
{2}
:\d
{2}
:\d
{2}\.\d
+)\s+(?<
log
>.*)$
    Time_Key    timestamp
    Time_Format %m/%d/%Y %H:%M:%S
    Time_Keep   On

Deployment Steps​

1. Create the directory structure and files​

mkdir
 -p Windows_IIS/{fluent-bit,vulnerable-sharepoint,provisioning}
cd
 Windows_IIS

Create each file above (Vagrantfile, provisioning scripts, ASPX pages, configs).

2. Start the VM​

# With libvirt:
sg libvirt -c 
"vagrant up"
# With VirtualBox:
vagrant up

First run: 15–30 minutes (downloads Windows box ~4–5 GB, provisions).

3. Connect and test​

vagrant rdp
# Credentials: vagrant / vagrant

In the VM browser:http://localhost:8080/

Vulnerable URLs:

  • http://192.168.56.10:8080/search.aspx?q=&lt;script&gt;alert(1)&lt;/script&gt;

  • [http://192.168.56.10:8080/documents.aspx?file=../../../etc/passwd](http://192.168.56.10:8080/documents.aspx?file=../../../etc/passwd)

  • http://192.168.56.10:8080/api.aspx?id=1' OR '1'='1

4. Ensure log backend is reachable​

Run a log collector on the host (e.g. port 8081) so Fluent Bit can send logs. The VM reaches the host at192.168.56.1.