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conducting-cloud-penetration-testing

This skill outlines methodologies for performing authorized penetration testing against AWS, Azure, and GCP cloud environments. It covers understanding the shared responsibility model for testing scope, leveraging cloud-specific attack tools like Pacu and ScoutSuite, exploiting IAM misconfigurations, testing for SSRF to cloud metadata services, and reporting findings aligned to MITRE ATT&CK Cloud matrix.

Quality

77%

Does it follow best practices?

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SecuritybySnyk

Passed

No findings from the security scan

Fix and improve this skill with Tessl

tessl review fix ./skills/conducting-cloud-penetration-testing/SKILL.md
SKILL.md
Quality
Evals
Security

Quality

Content

71%Weight 40%Scale 1-5

Reviews the quality of instructions and guidance provided to agents. Good implementation is clear, handles edge cases, and produces reliable results.

A highly actionable, well-sequenced cloud pentesting workflow with copy-paste-ready commands, explicit verification for destructive operations, and useful scenario/report templates. It loses points for explaining concepts Claude already knows, duplicating tool descriptions, and failing to reference the bundled references/ and scripts/ files at all.

Suggestions

Reference the bundle files where relevant, e.g. 'For scripted enumeration, see scripts/agent.py' in Step 2 and 'Full function reference: references/api-reference.md', so the provided bundle is discoverable.

Delete or drastically trim the Key Concepts entries that define widely known terms (Privilege Escalation, Lateral Movement, Shared Responsibility Model) and merge the Tools & Systems section with the remaining tool notes to remove duplication.

Add an end-of-engagement cleanup and validation checklist covering artifacts from all steps (backdoor users, assumed-role sessions, downloaded evidence) with a verify-after-cleanup loop.

DimensionReasoningScore

Conciseness

The body is mostly efficient and command-dense, but includes unnecessary explanation: the Key Concepts table defines concepts Claude already knows ('Privilege Escalation', 'Lateral Movement', IMDS, the Shared Responsibility Model) and the Tools & Systems section largely repeats the Pacu/ScoutSuite descriptions already given in Key Concepts. Not 4: the duplicated tool descriptions and textbook definitions of well-known concepts are more than minor over-explanation.

3 / 5

Actionability

Nearly every step provides copy-paste-ready, executable commands — ScoutSuite/Prowler/CloudFox invocations, AWS CLI enumeration and escalation commands, curl snippets for AWS/Azure/GCP metadata services, Pacu module runs, and IAM cleanup commands — and the examples cover the common cases from recon through reporting. Not 4: there are no significant gaps; placeholders (e.g. AKIAEXAMPLE, account IDs) are appropriate for a template.

5 / 5

Workflow Clarity

The 7-step workflow is clearly sequenced, and the destructive Step 6 operations include explicit verification ('Verify: Did GuardDuty generate Stealth:IAMUser/CloudTrailLoggingDisabled?') and cleanup commands, so the destructive-operation cap does not apply. Not 5: checkpoints are partial — there is no end-of-engagement validation/cleanup checklist ensuring artifacts from all steps (not just Step 6) are removed and no re-validation loop after remediation testing.

4 / 5

Progressive Disclosure

The body has good section structure (When to Use, Prerequisites, 7-step Workflow, Key Concepts, Tools, Scenarios, Output Format), but the bundle files that exist — references/api-reference.md and scripts/agent.py — are never referenced or signaled anywhere in the body, leaving them orphaned, and some inlined content (full report template, concept definitions) could live in those files. Not 4: the complete absence of navigation to provided bundle files is a bigger gap than 'minor organization gaps'; not 2 because section structure itself is solid, not minimal.

3 / 5

Total

15

/

20

Passed

Description

75%Weight 40%Scale 1-5

Based on the skill's description, can an agent find and select it at the right time? Clear, specific descriptions lead to better discovery.

A specific, well-scoped description with concrete named actions and strong distinctiveness. Its main weakness is the absence of any explicit 'Use when...' trigger clause, which caps completeness, and a few missing natural synonyms for trigger coverage.

Suggestions

Add an explicit trigger clause, e.g. 'Use when performing authorized penetration tests, cloud security assessments, or red team engagements against AWS, Azure, or GCP environments.'

Include common user synonyms such as 'pentest', 'cloud security assessment', and 'red team engagement' to broaden natural trigger coverage.

Trim the trailing whitespace and tighten the multi-sentence structure so the trigger clause fits naturally within the description.

DimensionReasoningScore

Specificity

The description lists multiple concrete, specific actions — 'performing authorized penetration testing against AWS, Azure, and GCP', 'leveraging cloud-specific attack tools like Pacu and ScoutSuite', 'exploiting IAM misconfigurations', 'testing for SSRF to cloud metadata services', and 'reporting findings aligned to MITRE ATT&CK Cloud matrix' — matching the comprehensive-coverage anchor. Not 4: the enumerated actions span tools, escalation, SSRF, and reporting with no notable coverage gaps.

5 / 5

Completeness

The 'what' is clear (authorized cloud pentesting covering shared responsibility scoping, tooling, IAM exploitation, SSRF, and MITRE ATT&CK reporting), but there is no 'Use when...' clause or equivalent trigger guidance, which caps completeness at 3 per the judging guidelines. Not 4: the 'when' is entirely missing rather than merely implicit or under-specified.

3 / 5

Trigger Term Quality

Good natural keyword coverage including 'penetration testing', 'AWS', 'Azure', 'GCP', 'IAM', 'SSRF', and named tools (Pacu, ScoutSuite) that users would plausibly say. Not 5: common variations such as 'pentest', 'cloud security assessment', or 'red team' are absent, leaving a few natural terms missing.

4 / 5

Distinctiveness Conflict Risk

The description carves out a clear niche — authorized cloud penetration testing with named offensive tools and cloud-provider-specific techniques — making it unlikely to trigger for the wrong skill. Not 4: no meaningful overlap risk with related skills; the tool names and cloud-specific attack techniques are distinct triggers.

5 / 5

Total

17

/

20

Passed

Validation

93%

Checks the skill against the spec for correct structure and formatting. All validation checks must pass before discovery and implementation can be scored.

Validation — 15 / 16 Passed

Validation for skill structure

CriteriaDescriptionResult

frontmatter_unknown_keys

Unknown frontmatter key(s) found; consider removing or moving to metadata

Warning

Total

15

/

16

Passed

Repository

mukul975/Anthropic-Cybersecurity-Skills

Path

skills/conducting-cloud-penetration-testing/SKILL.md

Reviewed

Table of Contents

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