Container File Abuse (ISO, IMG, LNK)
ISO, IMG, VHD, and other container formats bypassed Mark-of-the-Web protections; became primary delivery method after Microsoft blocked macros in 2022.
MITRE ATT&CK: T1566.001Timeline: The Cat and Mouse
2018 β Attack emerges β 2022 β Industry responds β 2023 β Attackers adapt β Present
The Evolution
| Phase | Period | What Happened |
|---|---|---|
| ATTACK | 2018 | ISO MOTW gap discovered - files inside mounted containers lack Zone.Identifier |
| Β | 2021 | NOBELIUM (Russia) uses ISO delivery in targeted attacks |
| PEAK | Feb 2022 | Microsoft blocks macros by default - attackers need new delivery method |
| Β | Q2 2022 | Mass pivot: QakBot, Emotet, IcedID shift to ISO/LNK delivery |
| RESPONSE | Nov 2022 | Microsoft patches CVE-2022-41091 - MOTW now propagates to ISO contents |
| Β | 2022 | Email gateways begin blocking ISO/IMG attachments |
| ADAPTATION | Jan 2023 | Attackers pivot to OneNote embedded files |
| Β | Apr 2023 | Microsoft blocks dangerous file types in OneNote |
| CURRENT | 2024+ | Password-protected archives, HTML smuggling, nested containers |
Key Events with Sources
| Date | Event | Significance | Source |
|---|---|---|---|
| 2018 | ISO MOTW gap identified | Files inside mounted ISOs lack Zone.Identifier | Outflank Research |
| Feb 2022 | Microsoft announces macro blocking | VBA macros from internet blocked by default | Microsoft Docs |
| Q2 2022 | Mass pivot to ISO/LNK | QakBot, Emotet, IcedID shift delivery methods | Proofpoint |
| Nov 2022 | CVE-2022-41091 patched | MOTW now propagates to ISO/IMG contents | Microsoft MSRC |
| Jan 2023 | OneNote abuse surge | Attackers pivot after ISO patch | Bleeping Computer |
| Apr 2023 | OneNote embedded files blocked | Microsoft restricts dangerous file types in OneNote | Microsoft |
| 2024 | Continued adaptation | Password-protected archives, HTML smuggling combinations | Cofense |
Overview
Mark-of-the-Web (MOTW) tags files downloaded from the internet, triggering security warnings and Protected View in Office. Container files (ISO, IMG, VHD) historically didnβt propagate MOTW to their contents. When Microsoft blocked macros by default in February 2022, attackers immediately pivoted to container-based delivery, exploiting this gap until Microsoft patched it in November 2022.
The Attack
Mark-of-the-Web Background
When you download a file, Windows adds an alternate data stream:
file.exe:Zone.Identifier
[ZoneTransfer]
ZoneId=3 (Internet)
This MOTW triggers:
- SmartScreen warnings before execution
- Protected View in Office
- Macro blocks in Office
- Security prompts
The Container Bypass (Pre-Patch)
1. Victim downloads: malware.iso (has MOTW)
2. Victim double-clicks ISO (Windows mounts as virtual drive)
3. Files INSIDE ISO β No MOTW!
4. payload.exe runs without any security warning
The MOTW didnβt propagate into the mounted containerβa gap that existed for years but became critical once macros were blocked.
Attack Chain
βββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββ
β EMAIL β
β β
β Subject: Invoice #2024-1234 β
β Attachment: Invoice_Details.iso (or .img) β
βββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββ
β
βΌ
βββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββ
β ISO FILE CONTENTS β
β β
β E:\ β
β βββ Invoice.lnk β Visible, looks like document β
β βββ payload.dll β Hidden file β
β βββ data.txt β Decoy content β
β β
β Invoice.lnk executes: β
β rundll32.exe payload.dll,EntryPoint β
βββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββ
β
βΌ
βββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββ
β EXECUTION β
β β
β - No MOTW on extracted files β
β - No SmartScreen warning β
β - No Protected View β
β - DLL executes immediately β
βββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββ
Container Types Abused
| Format | Extension | Mount Behavior | MOTW Status (Pre-Patch) |
|---|---|---|---|
| ISO 9660 | .iso | Auto-mount as drive | No propagation |
| IMG | .img | Auto-mount as drive | No propagation |
| VHD/VHDX | .vhd, .vhdx | Mount as drive | No propagation |
| ZIP | .zip | Depends on extractor | Inconsistent |
| 7z | .7z | Depends on extractor | Often stripped |
| RAR | .rar | Depends on extractor | Often stripped |
LNK File Abuse
Shortcut (LNK) files were ideal for container payloads:
- Execute arbitrary commands
- Display trusted icons (Word, PDF, etc.)
- Named with misleading extensions
- Not blocked like EXE attachments
LNK Obfuscation Techniques:
Icon Spoofing:
Visible Properties:
Target: Invoice.pdf
Icon: PDF document icon
Actual Command:
C:\Windows\System32\cmd.exe /c powershell -ep bypass -w hidden -e [BASE64]
Environment Variable Abuse:
Target: %ComSpec% /c calc.exe
β Expands to C:\Windows\System32\cmd.exe /c calc.exe
Path Padding (UI Truncation):
Target: C:\Windows\System32\cmd.exe [256 spaces] /c malware.exe
β
Truncated in properties UI
Real-World Campaigns
QakBot (2022):
HTML attachment β Downloads ISO β Contains LNK + DLL
LNK runs: regsvr32.exe payload.dll
Source: Proofpoint - QakBot Evolves
IcedID:
ISO file β Contains LNK disguised as document
LNK runs: rundll32.exe data.dll,update
Source: Elastic Security - IcedID Analysis
Bumblebee:
ISO file β Contains LNK + hidden folder with loader
LNK runs: PowerShell downloads next stage
Source: Google TAG - Bumblebee Loader
Emotet Return (2022):
Pivoted from macros to ISO after 10-month hiatus
LNK files invoking regsvr32 β Later moved to OneNote
Source: CISA - Emotet
Raw Email Headers (Container Delivery)
Typical phishing email delivering ISO container:
Return-Path: <invoice@supplier-invoices.com>
Received: from mail.supplier-invoices.com (mail.supplier-invoices.com [198.51.100.55])
by mx.target.com (Postfix) with ESMTPS id ISO001
for <accounts@target.com>; Thu, 30 Jan 2025 10:15:22 -0500 (EST)
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
d=supplier-invoices.com; s=mail;
h=from:to:subject:date;
bh=container123...;
b=isosig456...
Authentication-Results: mx.target.com;
dkim=pass header.d=supplier-invoices.com;
spf=pass smtp.mailfrom=invoice@supplier-invoices.com;
dmarc=pass (p=REJECT) header.from=supplier-invoices.com
From: "Accounts Payable" <invoice@supplier-invoices.com>
To: accounts@target.com
Subject: Invoice #INV-2025-0130 - Payment Required
Date: Thu, 30 Jan 2025 10:15:18 -0500
Message-ID: <iso-delivery-001@supplier-invoices.com>
MIME-Version: 1.0
Content-Type: multipart/mixed; boundary="container-boundary"
--container-boundary
Content-Type: text/plain; charset=UTF-8
Please find attached the invoice for January services.
Best regards,
Accounts Payable
--container-boundary
Content-Type: application/x-iso9660-image; name="Invoice-INV-2025-0130.iso"
Content-Disposition: attachment; filename="Invoice-INV-2025-0130.iso"
Content-Transfer-Encoding: base64
[Base64-encoded ISO containing LNK and malware]
--container-boundary--
Key observations:
- Authentication passes for attackerβs cousin domain
- ISO attachment with invoice-themed filename
- User mounts ISO, sees βInvoice.lnkβ with document icon
- Clicking LNK executes hidden payload
- No MOTW warnings (pre-patch)
The Response
Microsoft MOTW Propagation Fix (November 2022)
CVE-2022-41091: Windows Security Feature Bypass
Microsoft patched Windows to propagate MOTW to mounted container contents:
- MOTW now propagates into mounted ISOs/IMGs
- Contents inherit Zone.Identifier
- SmartScreen warnings restored
Source: Microsoft Security Update Guide
CVE-2022-44698: Additional MOTW bypass patched in December 2022.
Email Gateway Blocking
Organizations began blocking container file types at the email gateway:
Block attachments:
- *.iso, *.img, *.vhd, *.vhdx
- *.lnk (shortcuts in email = always suspicious)
- Nested: *.zip containing *.iso
- Password-protected containers
Group Policy Controls
Disable auto-mounting for organizations:
Computer Configuration β Administrative Templates β
Windows Components β File Explorer β
"Do not allow mounting of virtual disks" = Enabled
Attacker Adaptation
OneNote Pivot (January 2023)
When ISO was patched, attackers immediately moved to OneNote:
.one file with embedded VBS/HTA/BAT
User double-clicks "attachment" icon
Script executes without MOTW warning
Timeline:
- January 2023: OneNote abuse begins
- April 2023: Microsoft blocks dangerous file types in OneNote
Source: Microsoft - Blocked file extensions in OneNote
HTML Smuggling + Containers
Combining techniques to evade gateway blocking:
HTML attachment β JavaScript constructs ISO blob
β ISO downloaded locally (may bypass MOTW depending on browser)
β User manually opens downloaded ISO
Double-Packaging / Nested Containers
outer.zip (MOTW on ZIP)
βββ inner.iso (might lose MOTW on extraction)
βββ payload.lnk β malware (no MOTW)
Password-Protected Containers
Email body: "Password: invoice2024"
Attachment: protected.zip
βββ malware.iso
βββ payload
Gateway canβt scan contents; user extracts manually.
New Container Formats
After ISO/IMG heavily signatured:
- 7z archives
- RAR with extensions
- CAB files
- UDF images
- WIM (Windows Imaging Format)
Current State
Status: Active (Adapting)
Container abuse continues with adaptations:
| Vector | Current Status | Bypass Method |
|---|---|---|
| ISO/IMG | Patched (MOTW) | Password protection, HTML smuggling |
| VHD/VHDX | Patched | Less commonly blocked than ISO |
| LNK | Active | Sent via links, other containers |
| OneNote | Patched (2023) | Brief window of effectiveness |
| ZIP+ISO nested | Blocked by many | Some gateways miss nested containers |
| Password-protected | Active | Cannot be scanned by gateways |
The Pattern
This attack demonstrates a common cat-and-mouse pattern:
- Defense kills primary vector (macro blocking)
- Attackers find gap in defense (MOTW doesnβt propagate)
- Mass pivot to new vector (ISO/LNK becomes dominant)
- Industry responds (MOTW patch, gateway blocking)
- Attackers adapt again (OneNote, nested containers, password protection)
Detection Guidance
Email Analysis
Flag emails with:
- ISO, IMG, VHD, VHDX attachments
- Nested containers (ZIP with ISO inside)
- Password-protected archives with passwords in body
- Container files from external senders
Endpoint Monitoring
Watch for:
- ISO/IMG mount events from email downloads
- LNK execution from mounted drives or unusual paths
- rundll32/regsvr32 loading DLLs from mounted volumes
- PowerShell spawned from LNK parent process
SIEM Queries
Container mount from email:
event.type = "file_mount"
AND file.extension IN ("iso", "img", "vhd")
AND source.path CONTAINS "Downloads" OR source.path CONTAINS "Outlook"
Suspicious execution from mounted drive:
process.parent.name = "explorer.exe"
AND process.name IN ("powershell.exe", "cmd.exe", "rundll32.exe", "regsvr32.exe")
AND process.command_line CONTAINS drive_letter
AND drive_letter.type = "mounted_iso"
LNK spawning suspicious process:
process.parent.command_line CONTAINS ".lnk"
AND process.name IN ("powershell.exe", "cmd.exe", "mshta.exe", "wscript.exe")
Policy Recommendations
- Block ISO/IMG/VHD/VHDX at email gateway
- Block LNK files in email attachments (never legitimate)
- Disable auto-mount via GPO if business doesnβt require it
- Ensure all Windows systems have MOTW patches applied
- Train users on container file risks
- Monitor for password-protected archive + password in body pattern
Further Reading
For those wanting to go deeper down the rabbit hole:
Attack Research:
Defense Research:
Threat Intelligence:
- Proofpoint Annual Report - Tracks delivery mechanism trends
- Cofense Annual Report - Phishing trends and evasion techniques
What Killed It (or Weakened It)
| Defense | Introduced | Impact |
|---|---|---|
| Mark-of-the-Web Propagation | 2022 | Windows propagates MOTW to ISO/IMG contents (CVE-2022-41091) |
| ISO/IMG Attachment Blocking | 2022 | Email gateways block disk image attachments by default |
| VHD/VHDX Restrictions | 2023 | Additional container formats blocked at gateway |
| LNK File Restrictions | 2023 | Enhanced scrutiny on shortcut file execution from containers |