IoM OPSEC Advisor

Provides operational security methodology guidance. Does not duplicate concrete technical specifications (command usage, OPSEC scores, AV countermeasure matrices) — those are maintained centrally in the iom-pentest references. This skill focuses on mindset and decision frameworks.

Methodology: Five Questions Before Every Operation

Answer these five questions before executing any operation:

1. Do I know what is on the other side? Do not execute any risky operation without first running enum av / ps. Operating blind is the number-one OPSEC killer.

2. What is the detection surface of this operation? Every operation has a detection surface. Understanding it is the prerequisite for assessing risk:

Detection Dimension	Trigger Source	Monitored By
Process creation	New process, anomalous parent-child relationship	EDR, Sysmon Event 1
Memory operations	Process injection, cross-process read/write	EDR kernel callbacks
File on disk	Files written to disk	AV real-time scanning
Registry	Run keys, service registration	Sysmon Event 12/13
Network	Anomalous outbound traffic, lateral movement ports	NDR, firewall
Credential access	LSASS access	Credential Guard, EDR
Logging	ETW providers	SIEM, Defender ATP
API calls	Sensitive ntdll/kernel32 calls	EDR inline hooks

3. Is there an alternative with a smaller detection surface? Almost always yes. If your first instinct is logonpasswords, consider whether hashdump is sufficient.

4. What if it fails? Being blocked is not the same as being discovered, but retrying the same technique is self-exposure. Plan a fallback path.

5. Is this step actually necessary? If you can skip it, skip it. Every operation carries risk.

HITL Decision Framework

Triage user-requested operations by severity level:

Green Light (execute directly, inform the user)

• Read-only information gathering: sysinfo, whoami, ps, enum av
• Status checks: session, listener, pipeline list
• These operations have a minimal detection surface, but it is still worth telling the user what is happening

Yellow Light (present options, wait for confirmation)

• Operations with multiple implementation paths that differ significantly in OPSEC impact
• Privilege escalation, credential harvesting, persistence
• Present at least two options, annotating the detection surface of each

Red Light (strong warning, explicit confirmation required)

• Operations with an OPSEC score < 6
• Techniques known to be blocked by the current AV (per the case library)
• Operations that may destabilize the system (kernel exploits)
• Clearly state the risk, recommend alternatives, and wait for the user to explicitly confirm

Case Library

The case library is the core of experience accumulation. Each case records the outcome of a specific operation in a specific environment, serving as a reference for future decisions.

Cases are stored in the reference/cases/ directory, named as <operation-type>-<security-product>.md. See reference/case-template.md for the case format.

Using Cases

When a user requests an operation:

1. Identify the security products in the target environment
2. Search the case library for <operation-type>-<security-product>.md
3. If a matching case exists, cite the historical conclusion and skip techniques known to fail
4. If no matching case exists, assess per the methodology, execute, and record the result as a new case

Iteration Mechanism

Cases feed back into the iom-pentest references:

• A technique is consistently blocked by a specific AV — update the strategy matrix in opsec-guide.md
• A new safe execution path is discovered — update the corresponding phase reference in iom-pentest
• AV product behavior changes — update the security product identification table in opsec-guide.md

This way the case library drives iterative improvement of the iom-pentest specifications, rather than maintaining duplicates in both places.

References

Content	Location
Case template	reference/case-template.md
Case library	reference/cases/
AV countermeasures and execution methods (detailed specs)	iom-pentest/reference/opsec-guide.md — Strategy Matrix, Execution Method Selection
Technique quick-reference and OPSEC scores	iom-pentest/reference/technique-reference.md — Credential Harvesting, UAC Bypass