Infiltr8: The Red-Book
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  • The Red-Book
  • Red-Teaming
    • Reconnaissance
      • DNS Enumeration
      • Subdomains enumeration
      • Email Harvesting
      • Host Discovery
      • TCP/UDP Service Scanning
      • Vulnerability Scanning
      • Google Dorks
      • GitHub Recon
      • Files Metadata
      • 🛠️Maltego
      • 🛠️Specialized Search Engines
    • Execution
      • Code & Process Injection
        • Loading .NET Reflective Assembly
        • Loading .NET Assembly from Windows Script Hosting
        • Process Hollowing
        • WndProc Callback Shellcode Execution
        • Fibers Shellcode Execution
        • Vector Exception Handler Shellcode Execution
        • NtQueueApcThread & NtTestAlert Shellcode Execution
        • Thread Pool Callback Shellcode Execution
        • Module Stomping Shellcode Injection
        • Remote .NET Assembly Loading through WaaSRemediation DCOM Abuse
        • 🛠️DLL Injection
        • 🛠️CreateRemoteThread Injection
        • 🛠️Reflective DLL Injection
        • 🛠️NtMapViewOfSection Injection
        • 🛠️SetWindowHookEx Injection
        • 🛠️PoolParty
        • 🛠️MockingJay
      • Code Execution
        • CMSTP
        • MSBuild
        • MSHTA
        • Microsoft Office Execution
        • Windows Script Host (WSH)
        • Outlook Home Page Abuse (Specula)
        • Powershell Without Powershell.exe
        • RegSrv32
        • Scheduled Tasks
        • Services
        • Windows Library Files
        • HTML Help Files
        • WMI
        • Script Exploits
        • 🛠️Sliver
    • Initial Access
      • Network Services
      • Password Attacks
      • Phishing
        • HTML Smuggling
        • Phishing with Calendars (.ICS Files)
        • Phishing With Microsoft Office
          • MS Office - VBA (Macros)
          • MS Office - RTF Files RCE
          • MS Office - Custom XML parts
          • 🛠️MS Office - Excel 4.0 (XLM) Macros
          • 🛠️MS Office - VBA Stomping
          • 🛠️MS Office - Remote Dotm Template Injection
        • 🛠️Phishing via Proxy
          • Adversary in the Middle (AitM) Phishing
            • EvilGoPhish
            • Evilginx
            • Muraena
            • Modlishka
          • Browser in the Middle (BitM) Phishing
            • cuddlephish
            • EvilnoVNC
    • Persistence
      • Active Directory
      • Windows
        • Accessibility features Backdoor
        • AEDebug Keys Persistence
        • Image File Execution Options (IFEO) Persistence
        • Logon Triggered Persistence
        • LSA Persistence
          • Security Support Provider DLLs
          • Authentication Package
        • Natural Language 6 DLLs Persistence
        • Run Keys Persistence
        • Winlogon Persistence
        • WMI Event Subscription Persistence
      • Linux
        • SSH for Persistence
        • GSocket for Persistence
        • 🛠️Udev rules
    • Defense Evasion
      • Endpoint Detection Respons (EDR) Bypass
        • Bring Your Own Vulnerable Driver (BYOVD)
        • Safe Mode With Networking
        • Windows Defender Application Control (WDAC): Killing EDR
        • 🛠️Load Unsigned Drivers
        • 🛠️Minifilter Altitude
        • 🛠️Hypervisor Code Integrity (HVCI) Disallowed Images
        • 🛠️Windows Filtering Platform (WFP)
        • 🛠️Userland Hooking Bypass
      • UAC Bypass
      • AMSI Bypass
      • ETW evasion
      • Living Off The Land
        • Windows Sysinternals
        • LOLBAS Project
        • File Operations
        • File Executions
      • Signature Evasion
      • Obfuscation
        • PowerShell Obfuscation
        • 🛠️Commandline Obfusaction
        • 🛠️PE Obfuscation
        • 🛠️String Encryption
      • AppLocker Bypass
      • Mark-of-the-Web (MotW) Bypass
      • 🛠️PowerShell Constrained Language Mode (CLM) Bypass
      • 🛠️Kill Windows Defender
      • 🛠️Virtualization-based security (VBS) Bypass
        • 🛠️Credential Guard bypass
        • 🛠️hypervisor-protected code integrity (HVCI) Bypass
        • 🛠️Windows Defender Application Control (WDAC) Bypass
      • 🛠️Sandbox Evasion
    • Discovery
      • Active Directory
      • Windows
        • System Information
        • Processes & Services
        • Scheduled Tasks
        • Installed applications
        • Network Configuration
        • FIle/Folder ACLs
        • Knowing your Shell
        • Security Solutions
      • Linux
        • OS Details
        • 🛠️Process & Services
    • Privilege Escalation
      • Windows
        • Tools ⚙️
        • PowerShell Logging
        • Credentials In Files
        • Abusing Tokens
        • Insecure Services
          • Weak Service Permissions
          • Weak File/Folder Permissions
          • Weak Registry Permissions
          • Unquoted Service Path
        • AlwaysInstallElevated
        • AutoLogon Registry
        • Insecure Scheduled Tasks
          • Weak File/Folder Permissions
        • 🛠️DLL Hijacking
      • Linux
        • Kernel Exploits
          • OverlayFs Exploits
            • GameOverlayFs
            • CVE-2023-0386
            • CVE-2021-3493
          • CVE-2023-32233 (CAP_NET_ADMIN)
          • Dirty Pipe
          • 🛠️DirtyCow
          • 🛠️RDS
          • 🛠️Full Nelson
          • 🛠️Mempodipper
        • GLIBC Exploits
          • Looney Tunables
        • Polkit Exploits
          • PwnKit
          • D-Bus Authentication Bypass
        • Sudo Exploits
          • Sudo Binaries
          • Sudo Misconfigurations
          • Reuse Sudo Tokens
          • User Restriction Bypass
          • Pwfeedback BOF
          • Baron Samedit
          • Sudoedit Bypass
        • SUID Binaries
        • Script Exploits
          • Python
            • Pip Download Code Execution
            • PyInstaller Code Execution
            • Pytorch Models/PTH Files Code Execution
          • Ruby
          • Bash
          • Perl
        • Scheduled tasks
          • Cron Jobs
          • Systemd timers
        • Interesting Groups
          • Lxd
        • Capabilities
        • NFS no_root_squash/no_all_squash
        • Linux Active Directory
    • Credential Access
      • Password Stores
        • Windows Credential Manager
        • KeePass
        • Web Browsers
      • Unsecured Credentials
        • Credentials In Files
        • VNC Config
        • SSH Private Keys
        • Git Repositories
        • Veeam Backup
        • Network shares
        • Network protocols
      • OS Credentials
        • Windows & Active Directory
          • SAM & LSA secrets
          • DPAPI secrets
          • NTDS secrets
          • LSASS secrets
          • DCSync
          • Kerberos key list
          • Group Policy Preferences
          • AutoLogon Registry
          • In-memory secrets
          • Cached Kerberos tickets
        • Linux
          • Shadow File
          • In-memory secrets
          • Linux Cached Kerberos tickets
      • MITM and coerced auths
      • Password Attacks
        • Default, weak & Leaked Passwords
        • Generate Wordlists
        • Brute-Force
          • Online - Attacking Services
          • Offline - Password Cracking
      • Impersonation
    • Lateral Movement
      • Port Forwarding
      • TLS Tunneling (Ligolo-ng)
      • HTTP(s) Tunneling
      • SSH Tunneling
      • DNS Tunneling
      • SMB-based
      • WinRM
      • Remote WMI
      • DCOM
      • Scheduled Tasks (ATSVC)
      • Services (SVCCTL)
    • Exfiltration
      • Exfiltration over ICMP
      • Exfiltration Over DNS
      • Exfiltration Over HTTP(s)
      • Exfiltration Over SMB
  • Web Pentesting
    • Reconnaissance
      • Subdomains enumeration
      • WAF Enumeration
    • Infrastructures
      • DBMS
        • Enum Databases
        • Read/Write/Execute
      • DNS
        • Subdomain Takeover
      • Web Servers
        • Nginx
        • Apache
          • Apache Commons Text
          • Apache Tomcat
      • CMS
        • Wordpress
        • 🛠️Joomla
        • 🛠️Drupal
        • 🛠️Bolt CMS
      • Frameworks
        • Spring Framework
          • Spring Routing Abuse
          • Spring Boot Actuators
          • Spring View Manipulation
        • Werkzeug
        • 🛠️Django
        • 🛠️Flask
        • 🛠️Laravel
      • CGI
    • Web Vulnerabilities
      • Server-Side
        • NoSQL Injection
        • SQL Injection
          • UNION Attacks
          • Blind Attacks
            • Boolean Based
            • Time Based
            • Error Based
        • Insecure Deserialization
          • .NET Deserialization
          • Python Deserialization
          • PHP Deserialization
          • 🛠️Java Deserialization
          • 🛠️Ruby Deserialization
        • File Inclusion & Path Traversal
          • LFI to RCE
            • PHP Wrappers
            • Logs Poisoning
            • /proc
            • PHPInfo
            • PHP Sessions
            • Segmentation Fault
          • RFI to RCE
        • Command Injection
        • Brute-Force
        • SSTI (Server-Side Template Injection)
        • Exposed Git Repositories
        • 🛠️File Upload
      • Client-Side
        • XSS (Cross-Site Scripting)
        • CORS (Cross-origin resource sharing)
  • Network Pentesting
    • Network services
      • DNS
      • FastCGI
      • HTTP & HTTPS
      • LDAP
      • NFS
      • MS-RPC
      • MSSQL
      • NBT-NS (NetBIOS)
      • Oracle TNS
      • RDP
      • Rsync
      • SMB
      • SMTP
      • SNMP
      • SSH
      • WebDAV
      • WinRM
      • XMPP/Jabber
      • 🛠️RPC Port Mapper
      • 🛠️FTP
      • 🛠️Telnet
      • 🛠️MySQL
    • WiFi
      • 🛠️WEP
      • 🛠️WPA2
      • 🛠️WPS
    • Bluetooth
  • Active Directory Pentesting
    • Reconnaissance
      • Tools ⚙️
        • PowerView ⚙️
        • Responder ⚙️
        • BloodHound ⚙️
        • enum4linux ⚙️
      • Network
        • DHCP
        • DNS
        • NBT-NS
        • Port scanning
        • SMB
        • LDAP
        • MS-RPC
      • Objects & Settings
        • DACLs
        • Group policies
        • Password policy
        • LAPS
    • Movement
      • Credentials
        • Dumping
        • Cracking
        • Bruteforcing
          • Guessing
          • Spraying
          • Stuffing
        • Shuffling
      • MITM and coerced auths
        • ARP poisoning
        • DNS spoofing
        • DHCP poisoning
        • DHCPv6 spoofing
        • WSUS spoofing
        • LLMNR, NBT-NS, mDNS spoofing
        • ADIDNS poisoning
        • WPAD spoofing
        • MS-EFSR abuse (PetitPotam)
        • MS-RPRN abuse (PrinterBug)
        • MS-FSRVP abuse (ShadowCoerce)
        • MS-DFSNM abuse (DFSCoerce)
        • MS-EVEN abuse (CheeseOunce)
        • PushSubscription abuse
        • WebClient abuse (WebDAV)
        • Living off the land
        • 🛠️NBT Name Overwrite
        • 🛠️ICMP Redirect
      • NTLM
        • Capture
        • Relay
        • Pass the hash
      • Kerberos
        • Pre-auth bruteforce
        • Pass the key
        • Overpass the hash
        • Pass the ticket
        • Pass the cache
        • Forged tickets
          • Silver tickets
          • Golden tickets
          • Diamond tickets
          • Sapphire tickets
          • RODC Golden tickets
          • MS14-068
        • ASREQroast
        • ASREProast
        • Kerberoast
        • Delegations
          • (KUD) Unconstrained
          • (KCD) Constrained
          • (RBCD) Resource-based constrained
          • S4U2self abuse
          • Bronze Bit
        • Shadow Credentials
        • UnPAC the hash
        • Pass the Certificate - PKINIT
        • sAMAccountName spoofing
        • SPN-jacking
      • Netlogon
        • ZeroLogon
      • DACL abuse
        • AddMember
        • ForceChangePassword
        • Targeted Kerberoasting
        • WriteOwner
        • ReadLAPSPassword
        • ReadGMSAPassword
        • Grant ownership
        • Grant rights
        • Logon script
        • Rights on RODC object
      • Group policies
      • Trusts
      • Certificate Services (AD-CS)
        • Certificate templates
        • Certificate authority
        • Access controls
        • Unsigned endpoints
        • Certifried
      • Schannel
        • Pass the Certificate - Schannel
      • SCCM / MECM
        • Privilege Escalation
        • Post Exploitation
      • Exchange services
        • PrivExchange
        • ProxyLogon
        • ProxyShell
        • ProxyNotShell
      • Print Spooler Service
        • PrinterBug
        • PrintNightmare
      • Built-ins & settings
        • Builtin Groups
          • DNSAdmins
          • AD Recycle Bin
        • MachineAccountQuota
        • Pre-Windows 2000 computers
        • RODC
    • Persistence
      • Skeleton key
      • SID History
      • AdminSDHolder
      • GoldenGMSA
      • Kerberos
        • Forged tickets
        • Delegation to KRBTGT
      • Certificate Services (AD-CS)
        • Certificate authority
        • Access controls
        • Golden certificate
      • LAPS
      • 🛠️DC Shadow
      • 🛠️Access controls
  • 🛠️Cloud & CI/CD Pentesting
    • CI/CD
      • Ansible Pentesting
      • Artifactory Pentesting
      • Docker Registry
        • 🛠️HTTP API V2
      • 🛠️Kubernetes
      • 🛠️GitLab
      • 🛠️Github
      • 🛠️Gitea
      • 🛠️Jenkins
      • 🛠️Terraform
    • Azure Pentesting
      • Reconnaissance
        • Tools ⚙️
        • Unauthenticated Reconnaissance
        • Internal Reconnaissance
      • Movement
        • Credentials
          • Password Spraying
          • Token Manipulation
            • Pass-The-Cookie (PTC)
            • Pass the Certificate (Azure)
            • Pass the PRT
        • Aazure Resources
          • Key Vault
          • Storage Accounts
          • Virtual Machines
          • Automation
          • Databases
        • Role-Based Access
        • Conditional Access
        • Service Principals & Applications
        • Hybrid Identity
          • Password Hash Sync (PHS)
          • Pass-through Authentication (PTA)
          • Active Directory Federation Services (ADFS)
          • Seamless SSO
          • Cloud Kerberos Trust
        • Cross-Tenant Access
      • Persistence
    • GCP Pentesting
    • AWS Pentesting
  • 🛠️Smart Contracts Pentesting
    • Solidity
      • Vulnerabilities
        • Delegatecall Attack
        • Denial of Service Attack
        • Overflow & Underflow
        • Reentrancy Attack
        • Self Destruct Attack
        • Tx Origin Attack
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  1. Red-Teaming
  2. Defense Evasion

Mark-of-the-Web (MotW) Bypass

MITRE ATT&CK™ Subvert Trust Controls: Mark-of-the-Web Bypass - Technique T1553.005

Last updated 1 month ago

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Theory

Windows uses the to indicate that a file originated from the Internet, which gives an opportunity to perform additional inspection of the content. MotW also supplies the basis for prompting a user with an additional prompt when are opened.

MotW is applied to a file by appending a Alternate Data Stream (ADS) to the downloaded file that indicates the URL, and, optionally, the referrer URL from which the file originated. Antivirus (AV) and endpoint detection and response (EDR) products can use this information to supplement their reputation lookups.

However, Alternate Data Stream (ADS) requires an NTFS file system. We may bypass MotW by unsing container file formats that support other file systems outside of NTFS like .iso, .img, .vhd, and .vhdx. Windows can automatically mount these file systems, so all that we need it's the victim to double-click the container file and then double-click the embedded malicious file that won’t have MotW applied.

Practice

# Example packing Putty into an ISO file
.py putty-64bit-0.83-installer.msi putty-64bit.iso

After getting the putty-64bit.isoon our Windows target, we see that the .msi inside the ISO, is not MOTW-marked.

We can however notice that the ISO file itself will be MOTW-Marked.

Resources

(Python) can be use to packages payloads into output containers to evade Mark-of-the-Web flag. It supports: ZIP, 7zip, PDF, ISO, IMG, CAB, VHD, VHDX.

PackMyPayload
Mark-of-the-Web (MotW)
Microsoft Defender SmartScreen
high-risk extensions
Zone.Identifier
LogoMark of the Web Bypass - Red Canary Threat Detection ReportRed Canary
LogoSubvert Trust Controls: Mark-of-the-Web Bypass, Sub-technique T1553.005 - Enterprise | MITRE ATT&CK®
PackMyPayload Testings