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entra-conditional-access-bypass

Entra Conditional Access bypass — discover policy gaps, exploit legacy-auth protocols (IMAP/POP/SMTP-AUTH/EWS), spoof device/platform/UA/location conditions, abuse service-principals + app-based auth excluded from CA, and break-glass account misuse.

Quality

82%

Does it follow best practices?

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SecuritybySnyk

Critical

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SKILL.md
Quality
Evals
Security

Quality

Content

82%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 dense, operational skill body that consistently provides concrete executable commands with genuine domain tradecraft and no filler. It features a coherent phase-based workflow with decision-gate feedback loops, and its only shortcomings are minor: unresolved token/credential placeholders, a non-executable IMAP hint, and a few implicit validation checkpoints.

DimensionReasoningScore

Conciseness

The body is lean and command-first: every prose fragment conveys tenant-specific tradecraft Claude cannot be assumed to know (ROPC vs 'Other clients' CA scoping, PKeyAuth advertisement-vs-compliance caveat, audit-only policy state). Deprecation status is explicitly flagged ('deprecated but still works in some tenants'), and there is no padded explanation of concepts Claude already knows — matching the 'every token earns its place' anchor.

5 / 5

Actionability

Nearly every technique ships a concrete command (Graph API curl with jq filters, ROPC spray loop, swaks SMTP probe, openssl IMAP, MailSniper one-liner, named-location listing). It falls short of the copy-paste-ready 5 anchor due to unresolved placeholders (TOKEN=<GLOBAL_READER_OR_SECREADER> acquisition is never shown) and the IMAP section being a hint comment ('A1 LOGIN ...') rather than an executable command.

4 / 5

Workflow Clarity

A clear phase sequence (enumerate policy surface → exploit per gap class → chains → detection signatures → decision gate) with real feedback loops: AADSTS error codes route pivots ('53003 everywhere → pivot to phishing'), the SMTP probe validates with '235 Authentication succeeded', and break-glass abuse includes an explicit sacrificial-login validation. Not a 5 because some checkpoints are implicit — e.g., no verification that a minted service-principal token actually grants the claimed permissions before escalating to entra-privesc.

4 / 5

Progressive Disclosure

Single-file skill (~140 lines) with well-organized phase sections and clearly signaled one-level cross-skill references ('See entra-privesc § service-principal credential addition'). No bundle files exist, so there is no nesting risk, but the file exceeds the under-50-line simple-skill threshold and sections like the Tools catalog and detection signatures could arguably live in separate reference files — good structure with minor organization gaps, matching the 4 anchor.

4 / 5

Total

17

/

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 strong, highly specific description that concretely enumerates the full range of CA bypass techniques with excellent domain keyword coverage and clear distinctiveness. Its one structural weakness is the complete absence of a 'Use when...' trigger clause, which both caps completeness and leaves natural trigger phrases like 'MFA bypass' or 'Azure AD' unsurfaced.

Suggestions

Append an explicit trigger clause, e.g. 'Use when assessing or bypassing Entra Conditional Access / Azure AD MFA policies, testing legacy-auth exposure, or attacking break-glass accounts.'

Include the natural synonyms users would actually say — 'MFA bypass', 'Azure AD', 'password spray' — alongside the current protocol jargon to improve trigger-term coverage.

Consider referencing the metadata when_to_use terms (mfa bypass, basic auth, trusted location) inside the description itself so the trigger guidance lives where users will read it.

DimensionReasoningScore

Specificity

The description enumerates multiple specific concrete actions across the full bypass surface: 'discover policy gaps', 'exploit legacy-auth protocols (IMAP/POP/SMTP-AUTH/EWS)', 'spoof device/platform/UA/location conditions', 'abuse service-principals + app-based auth excluded from CA', and 'break-glass account misuse'. This matches the comprehensive-coverage anchor rather than the 4 anchor, which allows minor gaps in coverage.

5 / 5

Completeness

The 'what' is clearly stated (the enumerated bypass techniques), but there is no 'Use when...' clause or equivalent explicit trigger guidance anywhere in the description — the rubric guideline caps completeness at 3 for this. It is not a 4 because the 'when' is entirely absent rather than merely imprecise.

3 / 5

Trigger Term Quality

Good keyword coverage including 'Conditional Access bypass', 'legacy-auth', 'IMAP/POP/SMTP-AUTH/EWS', 'service-principals', 'break-glass'. However, common natural phrases users would say such as 'MFA bypass', 'Azure AD', or 'password spray' are absent, so it falls short of the comprehensive-synonyms anchor.

4 / 5

Distinctiveness Conflict Risk

The description occupies a clear niche — Entra Conditional Access specifically, with named protocols (IMAP/POP/SMTP-AUTH/EWS), device/platform/location spoofing, and break-glass abuse — making it clearly distinguishable from adjacent skills like entra-enum, entra-privesc, or device-code phishing. Minimal conflict risk.

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

metadata_version

'metadata.version' is missing

Warning

Total

15

/

16

Passed

Repository

PurpleAILAB/Decepticon

Path

packages/decepticon/decepticon/skills/standard/cloud/entra-conditional-access-bypass/SKILL.md

Reviewed

Table of Contents

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