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CloudSecure Implementation Progress

Project: CloudSecure Assessment Platform Author: CloudSecure Contributors Started: 2025-01-23 Current Sprint: Deployed & Operational Last Deployment: 2026-03-05 (Region: eu-west-1)

Progress Overview

Sprint Status Progress
Sprint 1: Foundation ✅ Complete 100%
Sprint 2: Core Assessment ✅ Complete 100%
Sprint 3: Analysis Modules ✅ Complete 100%
Sprint 4: Prowler Integration ✅ Complete 100%
Sprint 5: AI & Reports ✅ Complete 100%
Sprint 6: Polish ✅ Complete 100%
Post-Sprint: CLI & Distribution ✅ Complete 100%

Post-Sprint: CLI & Distribution (2026-03)

  • Python CLI tool (pip install cloudsecure) with SigV4-signed API calls
  • PyPI packaging with pyproject.toml, GitHub Actions publish workflow
  • install.sh — curl-downloadable CLI installer
  • deploy.sh — interactive deployment with --upgrade and --setup-role flags
  • destroy.sh — interactive teardown with multi-layer confirmation
  • Makefile with build, deploy, test, lint targets
  • .env.example configuration template
  • Prowler made optional (SKIP_PROWLER=true, skipProwler CDK context)
  • Runtime --scope filtering for targeted assessments
  • CLI v0.2.0: scope filtering, improved error messages
  • Bug fixes: DynamoDB Decimal serialization, presigned URL SigV4, reportS3Key persistence, format validation

Sprint 1: Foundation

Infrastructure Setup

  • Initialize git repository with branch strategy (main/test/dev)
  • Create CDK TypeScript project structure
  • Create Python project structure for lambdas
  • Set up pyproject.toml with dependencies

Storage Stack

  • Create KMS key construct
  • Create S3 bucket with encryption and lifecycle
  • Create DynamoDB assessments table
  • Create DynamoDB findings table
  • Create DynamoDB context table (CRF entities)
  • Add GSI for accountId-index, severity-index, entityType-index

API Stack

  • Create API Gateway REST API
  • Configure IAM authorization
  • Add POST /assessments endpoint (stub)
  • Add GET /assessments/{id} endpoint (stub)
  • Add GET /assessments/{id}/report endpoint (stub)
  • Add CRF context endpoints (/customers/{id}/context)

Python Models

  • Implement models.py (Assessment, Finding, Pydantic schemas)
  • Implement crf_models.py (CRF context entities)
  • Implement aws_client.py (STS AssumeRole helper)

CI/CD Pipeline

  • Create CI/CD workflow
  • Add CDK synth validation
  • Add Python linting (Ruff, Black)
  • Create deploy workflow for dev/test/main

Sprint 2: Core Assessment

Lambda Functions

  • Create shared Python module structure
  • Implement models.py (Pydantic schemas)
  • Implement aws_client.py (STS helper)
  • Implement validate_role Lambda
  • Implement discovery_module Lambda

Orchestration

  • Create Step Functions state machine
  • Implement ValidateRole state
  • Implement Discovery state
  • Add error handling states
  • Connect API Gateway to Step Functions

API Lambda Handlers

  • Implement start_assessment Lambda (POST /assessments)
  • Implement get_assessment Lambda (GET /assessments/{id})
  • Implement list_assessments Lambda (GET /assessments)
  • Implement get_report Lambda (GET /assessments/{id}/report)

Testing

  • Set up pytest with moto
  • Write unit tests for shared modules (38 tests, 93% coverage)
  • Write unit tests for Lambda handlers
  • Configure LocalStack for integration tests

Sprint 3: Analysis Modules

IAM Analyzer

  • Detect unused credentials (>90 days)
  • Detect users without MFA
  • Detect overprivileged roles/users
  • Detect wildcard trust policies
  • Check root account (MFA, access keys)
  • Check password policy

Network Analyzer

  • Detect permissive security groups (0.0.0.0/0)
  • Detect public-facing EC2 instances
  • Check VPC Flow Logs enablement
  • Check default VPC usage

S3 Analyzer

  • Detect public buckets (ACL/policy)
  • Check encryption status
  • Check access logging
  • Check versioning
  • Check account-level public access block

Encryption Analyzer

  • Detect unencrypted EBS volumes
  • Check EBS default encryption
  • Detect unencrypted RDS instances
  • Detect publicly accessible RDS
  • Detect unencrypted EFS file systems

CloudTrail Analyzer

  • Check trail configuration (multi-region, logging)
  • Check log file validation
  • Check KMS encryption
  • Detect root account usage (90 days)
  • Check CloudWatch metric filters

Integration

  • Add parallel branches to Step Functions
  • Implement findings normalization (base analyzer class)
  • Implement aggregate findings Lambda
  • Write unit tests for analyzers

Sprint 4: Prowler Integration

Container Setup

  • Create Dockerfile for Prowler Lambda
  • Configure ECR repository
  • Build and push container image (manual pre-build to ECR)
  • Test container locally

Lambda Function

  • Implement prowler_scanner Lambda
  • Configure CIS AWS 1.4 checks (subset of critical checks)
  • Parse Prowler JSON output (JSON lines format)
  • Normalize findings to standard schema
  • Created placeholder Lambda (returns empty findings when container build disabled)

Integration

  • Add Prowler state to Step Functions (parallel with other analyzers)
  • Handle 15-minute timeout (14 min Prowler + 1 min buffer)
  • Write integration tests

Note: Prowler 5.17.0 now active. Container pre-built and pushed to ECR, deployed as DockerImageFunction. All 7 analyzers (IAM, Network, S3, Encryption, CloudTrail, Native Services, Prowler) are fully operational.

Sprint 5: AI & Reports

Aggregate Findings

  • Implement aggregate_findings Lambda (Sprint 3)
  • Deduplicate findings
  • Calculate severity distribution
  • Prepare findings summary for AI

AI Synthesis

  • Configure Bedrock access (IAM policy)
  • Implement finding correlation prompt
  • Implement executive summary prompt
  • Implement remediation guidance prompt
  • Calculate risk scores (weighted by severity)

Report Generator

  • Create WeasyPrint Lambda layer (PDF - future)
  • Design HTML report template (Jinja2)
  • Implement PDF generation (future)
  • Implement JSON export
  • Implement CSV export
  • Generate pre-signed URLs

Sprint 6: Polish

Native Service Puller

  • Pull SecurityHub findings (if enabled)
  • Pull GuardDuty findings (if enabled)
  • Pull Config compliance (if enabled)
  • Handle disabled services gracefully

Customer Onboarding

  • Finalize CloudFormation template
  • Finalize Terraform module
  • Write onboarding documentation (Terraform README)

Documentation

  • API documentation
  • User guide
  • Operations runbook

Security Hardening

  • Security review
  • Penetration testing
  • Fix identified issues

Changelog

2026-01-23 (Prowler Re-enablement)

  • Re-enabled Prowler Scanner after fixing Prowler 5.x compatibility issues
  • Upgraded from Prowler 4.x to 5.17.0
  • Fixed handler.py for Prowler 5.x CLI changes:
    • Removed --compliance option (mutually exclusive with --checks in v5.x)
    • Changed --filter-region to space-separated arguments (not comma-separated)
    • Updated output format from json to json-ocsf
  • Updated JSON parsing to handle OCSF array format (Prowler 5.x outputs JSON arrays, not JSON lines)
  • Changed lambda-stack.ts from placeholder Lambda to DockerImageFunction using pre-built ECR image
  • Added chmod 644 to Dockerfile for Lambda runtime permissions
  • Test assessment detected 47 Prowler security findings

2026-01-23 (Production Deployment)

  • Successfully deployed to AWS (eu-west-1)
  • Fixed Prowler container build issues by creating placeholder Lambda
  • Fixed validate_role Lambda: removed unsupported MaxResults from describe_regions
  • Added analyzers module to Lambda shared layer
  • Fixed Native Service Puller: store findings in DynamoDB to avoid Step Functions 256KB limit
  • Added jinja2 package to Lambda layer for HTML report generation
  • Created API Gateway CloudWatch Logs IAM role
  • First successful assessment completed with 64 findings (Risk Score: 22/LOW)
  • Reports generated: HTML, JSON (4MB), CSV with pre-signed S3 URLs

2025-01-23 (Sprint 6)

  • Implemented Native Service Puller Lambda for AWS security services
  • Pulls from SecurityHub, GuardDuty, AWS Config (with graceful handling if not enabled)
  • Created CloudFormation onboarding template with ExternalId security
  • Created Terraform module with variables, outputs, and README documentation
  • Onboarding templates include ReadOnlyAccess, SecurityAudit, and custom security policies
  • Added Native Service Puller to parallel analyzer branch in Step Functions
  • All 6 sprints complete - full assessment pipeline implemented

2025-01-23 (Sprint 5)

  • Implemented AI Synthesis Lambda with Amazon Bedrock (Claude 3 Haiku)
  • Created intelligent prompts for executive summary, key findings, patterns, remediation
  • Implemented risk score calculation (weighted by severity)
  • Created Report Generator Lambda with HTML, JSON, CSV exports
  • Designed professional HTML report template with Jinja2
  • Added pre-signed S3 URLs for secure report download
  • Extended Step Functions workflow with AI synthesis and report generation
  • Full assessment pipeline now: Validate -> Discover -> Analyze (parallel) -> Aggregate -> AI Synthesis -> Generate Reports

2025-01-23 (Sprint 4)

  • Implemented Prowler Scanner Lambda as container image
  • Created Dockerfile with AWS CLI v2 and Prowler 4.x
  • Created ECR repository with lifecycle rules (keep 5 images)
  • Implemented handler with cross-account role assumption
  • Configured subset of CIS AWS 1.4 critical checks for faster execution
  • Added JSON lines output parsing and CloudSecure finding normalization
  • Integrated Prowler into Step Functions parallel analyzer branch
  • Set 15-minute timeout with 3GB memory and 1GB ephemeral storage

2025-01-23 (Sprint 3)

  • Implemented 5 security analyzers (IAM, Network, S3, Encryption, CloudTrail)
  • Created base analyzer class with common functionality
  • Implemented aggregate findings Lambda for collecting results
  • Updated Step Functions with parallel analyzer execution
  • All analyzers run concurrently for faster assessment
  • CIS AWS 1.4 compliance mappings added to findings

2025-01-23 (Sprint 2 - Continued)

  • Implemented API Lambda handlers (start, get, list, report)
  • Connected API Gateway to Step Functions via Lambda integration
  • Updated API Stack with Lambda integrations (replaced mock integrations)
  • Full end-to-end assessment flow now functional

2025-01-23 (Sprint 2)

  • Implemented validate_role Lambda handler
  • Implemented discovery_module Lambda handler
  • Created Lambda Stack (CDK) with shared layer
  • Created Orchestration Stack with Step Functions state machine
  • Added unit tests for shared modules (38 tests, 93% coverage)
  • Updated CDK app with Lambda and Orchestration stacks

2025-01-23 (Sprint 1)

  • Created project specification
  • Created implementation plan
  • Set up README.md, CLAUDE.md, IMPLEMENTATION.md
  • Initialized git repository with dev/test/main branches
  • Created Storage Stack (DynamoDB tables, S3, KMS)
  • Created API Stack (API Gateway with IAM auth)
  • Created shared Python modules (models, crf_models, aws_client)
  • Set up CI/CD pipeline

First Successful Assessment

Date: 2026-01-23

Results

Metric Value
Risk Score 22 (LOW)
Total Findings 64
Critical 0
High 2
Medium 2
Low 60

Key Findings

  1. [HIGH] No CloudTrail trail logging management events
  2. [HIGH] Root account used 43 times in last 90 days

Reports generated in HTML, JSON, and CSV formats via pre-signed S3 URLs.

Notes

Technical Decisions

  • Prowler: Lambda Container Image (Prowler 5.17.0) - Pre-built to ECR, deployed as DockerImageFunction
  • Compliance: CIS AWS 1.4 first, others later
  • Multi-Account: Phase 2 (single-account first)
  • Testing: moto (unit) + LocalStack (integration)
  • Lambda Layer: Uses Docker to build packages with correct Linux (manylinux2014_x86_64) binaries

Blockers

  • Prowler Container Build: Docker I/O errors during CDK deploy - using placeholder Lambda RESOLVED (2026-01-23): Pre-built container to ECR, updated to DockerImageFunction

Risks

  • Prowler execution time may exceed Lambda limits
  • Bedrock token costs need monitoring
  • WeasyPrint packaging complexity

Future Roadmap

Instance Security Scan (Sprint 7+)

Instance-level threat assessment via SSM. Extends CloudSecure from account posture to live instance analysis.

  • Spec: docs/features/instance-scan-spec.md
  • CLI: cloudsecure scan --instance i-0abc123 --account 123456789012
  • Modes: live (production, attack vector analysis) / forensic (isolated, incident investigation)
  • Access: SSM RunCommand (agentless, no SSH)
  • AI: Bedrock analyzes system state and identifies how an attacker would exploit it
Sprint Scope
Sprint 7 MVP: Tier 1 system inventory, Amazon Linux, JSON report
Sprint 8 Web app analysis, Ubuntu, HTML reports, forensic mode
Sprint 9 Threat indicators, CVE matching, batch scan, all distros

Deployment Fixes Applied (2026-01-23)

  1. Prowler Container: Disabled DockerImageFunction, created placeholder Lambda
  2. EC2 API Fix: Removed unsupported MaxResults parameter from describe_regions
  3. Lambda Layer: Added analyzers module to shared layer
  4. Step Functions Limit: Modified Native Service Puller to store findings in DynamoDB (avoid 256KB state limit)
  5. Jinja2: Added to Lambda layer for HTML report generation
  6. API Gateway: Created CloudWatch Logs role for API Gateway account settings