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Introduction:
Cloud security isn’t just about checking IAM boxes—it’s understanding how attackers abuse misconfigured S3 buckets, escalate privileges via metadata services, and pivot through containers. In this article, we reverse-engineer a 6‑month roadmap from lead penetration tester Michael Eru, adding hands‑on Linux/Windows commands, attack simulations, and defensive automation to turn theory into muscle memory.
Learning Objectives:
- Master IAM policies, role abuse, and privilege escalation in AWS/Azure/GCP
- Simulate real‑world cloud attacks (metadata service, public exposure, container breakout)
- Build and break Infrastructure as Code (Terraform) with CI/CD security gates
- Harden Kubernetes clusters using RBAC, pod security, and image scanning
- Document and communicate cloud security findings like a professional
You Should Know:
- Month 1 – Core Fundamentals & First Cloud CLI
Start with Linux, networking, and one cloud provider. Run these commands to verify your environment before touching cloud consoles.
Linux (Ubuntu/Debian) – Network & API basics
DNS resolution & HTTP headers dig google.com +short curl -v https://api.github.com -H "Accept: application/json" Check open ports & processes sudo netstat -tulpn | grep LISTEN ps aux | grep sshd
Windows (PowerShell)
Resolve-DnsName google.com Invoke-WebRequest -Uri https://api.github.com | Select-Object -ExpandProperty Headers Get-1etTCPConnection -State Listen Get-Process -1ame sshd
Step‑by‑step: Install AWS CLI (pip install awscli), configure with aws configure, and list S3 buckets (aws s3 ls). Verify API access with aws sts get-caller-identity. This grounds you in cloud identity before touching permissions.
- Month 2 – IAM Deep Dive: Policies, Roles & Misconfigurations
Most cloud breaches start with over‑privileged roles. Learn to enumerate and fix them.
AWS CLI – Enumerate IAM risks
List all users and their attached policies
aws iam list-users --query 'Users[].UserName' --output text | xargs -I {} aws iam list-attached-user-policies --user-1ame {}
Find unused roles (attackers love these)
aws iam list-roles --query 'Roles[?RoleLastUsed==null].RoleName'
Simulate permissions for a given user
aws iam simulate-principal-policy --policy-source-arn arn:aws:iam::123456789012:user/bob --action-1ames s3:DeleteBucket
Step‑by‑step: Create a custom IAM policy that allows `s3:GetObject` only on a specific prefix. Then attempt to access a different prefix—watch the AccessDenied. Next, create an EC2 instance with an instance profile that has overly broad S3 permissions. From the instance, run `curl http://169.254.169.254/latest/meta-data/iam/security-credentials/` to steal temporary credentials. This is the infamous metadata service attack.
3. Month 3 – Attack Simulation: IAM Escalation & Public Exposure
Use intentionally vulnerable labs to think like a red teamer.
Deploy AWSGoat (on Linux)
git clone https://github.com/ine-labs/AWSGoat.git cd AWSGoat terraform init && terraform apply -auto-approve After deployment, find the public S3 bucket via aws s3 ls | grep "awsgoat" Attempt to list contents without credentials aws s3 ls s3://<bucket-1ame> --1o-sign-request
Step‑by‑step: Inside AWSGoat, exploit a misconfigured Cognito identity pool to assume an admin role. Use `aws sts assume-role-with-web-identity. Then leverage that role to modify a Lambda function and exfiltrate environment variables. Defensively, enable S3 Block Public Access and set bucket policies withaws s3api put-bucket-policy –bucket
- Month 4 – DevSecOps: Terraform & GitHub Actions Security
Secure pipelines before they reach production. Detect secrets and misconfigurations in code.
Terraform validation & tflint
Install tflint, check for hardcoded secrets tflint --init tflint --enable-rule=aws_iam_no_hardcoded_secrets Scan for public S3 buckets terraform plan | grep "acl = \"public-read\""
GitHub Actions – Secrets scanning (add to `.github/workflows/security.yml`)
name: Secret Scanner
on: [bash]
jobs:
trufflehog:
runs-on: ubuntu-latest
steps:
- uses: actions/checkout@v3
- name: TruffleHog OSS
run: docker run -v ${{ github.workspace }}:/dir trufflesecurity/trufflehog:latest github --repo https://github.com/${{ github.repository }}
Step‑by‑step: Write a Terraform module that creates an RDS instance without encryption. Run `tfsec` (or checkov) to detect the violation. Then add a pre-commit hook with `terrascan` to block the commit. On Windows, use `terraform validate` and `checkov -d .` inside PowerShell.
- Month 5 – Kubernetes Security: RBAC, Pod Security & Image Scanning
Containers introduce new attack surfaces—kubectl is your weapon and shield.
Linux – K8s attack & defense
Get pods with overly permissive service accounts kubectl get pods --all-1amespaces -o json | jq '.items[] | select(.spec.serviceAccountName != "default") | .metadata.namespace + "/" + .metadata.name' Attempt to exec into a privileged container kubectl exec --stdin --tty <pod-1ame> -- /bin/bash Inside the container, try to mount host filesystem cat /proc/1/mountinfo | grep docker
Image scanning with Trivy
trivy image nginx:latest --severity CRITICAL trivy k8s --report summary cluster/ --severity HIGH
Step‑by‑step: Deploy a vulnerable Kubernetes Goat cluster (kubectl apply -f https://raw.githubusercontent.com/madhuakula/kubernetes-goat/main/kubernetes-goat.yaml`). Exploit a pod with hostPath mount to read/etc/kubernetes/admin.conf. Defensively, enforce Pod Security Standards withkubectl label namespace default pod-security.kubernetes.io/enforce=restricted`. Then run `kube-bench` to check CIS benchmarks.
- Month 6 – Build, Document & Simulate Incidents
Stop consuming tutorials—create a detection lab and write a post‑mortem.
Build a cloud detection lab (AWS – CloudTrail + GuardDuty)
Enable CloudTrail in all regions
aws cloudtrail create-trail --1ame my-detection-trail --s3-bucket-1ame my-logs-bucket --is-multi-region-trail
aws cloudtrail start-logging --1ame my-detection-trail
Simulate a brute force attempt (run from EC2)
for i in {1..20}; do aws sts assume-role --role-arn "arn:aws:iam::123456789012:role/attacker-target" --role-session-1ame "Brute$i" --duration-seconds 900; done
Step‑by‑step: Write a Python script that queries CloudTrail for `AssumeRole` failures and sends a Slack alert. Then create a GitHub repo with a `README.md` documenting the entire 6‑month journey—include diagrams, IAM policies you broke, and how you fixed them. Communication skills get you hired.
What Undercode Say:
- Practical beats paper – Certifications (CASA, CAP) help, but rebuilding AWSGoat and exploiting your own Kubernetes cluster proves real competence.
- IAM is the new perimeter – Master
sts:AssumeRole, wildcard policies, and condition keys. Most breaches start here, not with zero‑days. - Attack to defend – Simulating metadata service abuse or container breakout rewires your brain. If you can’t break it, you can’t lock it.
Prediction:
- +1 Cloud security roles will demand less “years of experience” and more demonstrable GitHub portfolios with offensive labs – this roadmap shortens the gap from months to weeks.
- -1 As Infrastructure as Code adoption skyrockets, misconfigured Terraform modules will become the 1 cloud breach vector, outpacing even S3 leaks.
- +1 AI‑powered IAM policy analyzers (like Amazon IAM Access Analyzer) will automate 70% of privilege escalation discovery, forcing attackers to shift to identity‑federated supply chain attacks.
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