security-assessment

name: security-assessment description: Deep-dive security posture assessment by analyzing IAM policies, encryption configs, network rules, and security controls in code to produce evidence-backed findings aligned with the Well-Architected Security pillar. not_for: cost optimization, performance tuning, reliability assessment, migration planning, operational excellence, full cross-pillar WA review version: 2.0.0

Security Assessment

Step 1: Gather context

Ask the user:

What workload or AWS environment would you like me to assess for security? Please share:

• Workload name and code packages/directories to analyze
• Compliance requirements (SOC2, HIPAA, PCI-DSS, FedRAMP, GDPR, etc.)
• Known concerns (optional)

If context is already provided or you are in a codebase with IaC, proceed directly.

Step 2: Identity and Access Management Discovery

Analyze all IAM configurations in the codebase.

You MUST examine:

• IAM role definitions (trust policies and permission policies)
• IAM policy documents (managed and inline)
• Service-linked roles and permission boundaries
• Resource-based policies (S3 bucket policies, KMS key policies, SQS policies)
• Cognito/Identity Center configurations
• API Gateway authorizers
• Lambda execution roles

For each IAM resource, document:

• File path and line numbers
• Actions allowed (flag wildcards)
• Resources scoped (flag wildcards)
• Trust relationships (who can assume)
• Whether least privilege is followed

You MUST flag as HIGH RISK:

• Any "Action": "*" or "Action": "service:*" on mutating actions
• Any "Resource": "*" on policies that allow write/delete operations
• Cross-account trust with overly broad conditions
• Missing Condition blocks on sensitive operations
• IAM policies attached to * principals
• Long-lived credentials (access keys in code or config)

Step 3: Encryption and Data Protection Discovery

Analyze encryption configurations across all resources.

You MUST examine:

• KMS key definitions and key policies
• Encryption-at-rest settings on all storage (S3, EBS, RDS, DynamoDB, EFS, Secrets Manager)
• Encryption-in-transit settings (TLS configs, listener rules, security policies)
• Certificate management (ACM, self-signed)
• Secrets management (Secrets Manager, Parameter Store SecureString, environment variables)
• Data classification tags

You MUST flag as HIGH RISK:

• Any storage resource without encryption at rest enabled
• TLS versions below 1.2 on any listener or endpoint
• Security policies allowing weak cipher suites (RC4, DES, 3DES, MD5-based MACs)
• Self-signed or expired certificates in production configurations
• Secrets in environment variables, hardcoded strings, or config files (instead of Secrets Manager/Parameter Store)
• KMS keys without rotation enabled
• S3 buckets without default encryption

Step 4: Network Protection Discovery

Analyze all network security configurations.

You MUST examine:

• VPC definitions (subnets, route tables, internet gateways)
• Security group rules (ingress and egress)
• Network ACLs
• WAF rules and web ACLs
• VPC endpoints (interface and gateway)
• NAT Gateways and their placement
• Load balancer security (listeners, target groups, security policies)
• API Gateway endpoint types and throttling

You MUST flag as HIGH RISK:

• Security group ingress 0.0.0.0/0 on ports other than 443/80
• Security group ingress 0.0.0.0/0 on SSH (22) or RDP (3389)
• Public subnets hosting databases or internal services
• Missing VPC endpoints for S3/DynamoDB (traffic going through NAT/internet)
• No WAF on internet-facing endpoints
• Overly permissive egress rules (all traffic to all destinations)

---STOP--- Checkpoint: Discovery complete — present findings before evaluation.

Here is what I discovered about your security posture:

• IAM: {summary of roles, policies, and access patterns found}
• Encryption: {summary of encryption-at-rest and in-transit status}
• Network: {summary of VPC, security groups, WAF configuration}

Shall I proceed with the full security evaluation, or would you like to adjust scope?

Do NOT proceed past this point until the user explicitly confirms.

Step 5: Detection and Response Discovery

Analyze security monitoring and incident response configurations.

You MUST examine:

• CloudTrail configurations
• GuardDuty enablement
• Security Hub configurations
• Config Rules
• VPC Flow Log settings
• CloudWatch alarms for security events (root login, unauthorized API calls)
• Automated response configurations (Lambda remediation, Step Functions)
• S3 access logging

Step 6: Compute Protection Discovery

Analyze compute security configurations.

You MUST examine:

• Lambda function configurations (runtime, layers, VPC attachment, reserved concurrency)
• ECS/EKS task definitions (privileged mode, user, capabilities, secrets injection)
• EC2 launch templates (IMDSv2, user data, security groups)
• Container image sources and scanning configurations
• SSM Session Manager configurations (vs SSH access)

You MUST flag as HIGH RISK:

• Containers running in privileged mode without justification
• EC2 instances with IMDSv1 enabled (hop limit > 1 without IMDSv2 required)
• Lambda functions with overly broad VPC access
• No container image scanning configured
• SSH access enabled where SSM Session Manager would suffice

Step 7: Evaluate against WA Framework questions

For each question, provide: Status, Evidence (file:line), Gaps, Risk.

SEC 1 — How do you securely operate your workload?

• Look for: security baselines, account separation, threat detection, automated response
• Evidence: Config rules, GuardDuty configs, security automation

SEC 2 — How do you manage identities for people and machines?

• Look for: centralized identity, role separation, credential lifecycle, MFA configurations
• Evidence: Identity Center configs, IAM role trust policies, Cognito settings

SEC 3 — How do you manage permissions for people and machines?

• Look for: least privilege, permission boundaries, access analysis, regular review process
• Evidence: IAM policies, permission boundary ARNs, Access Analyzer configs

SEC 4 — How do you detect and investigate security events?

• Look for: CloudTrail, GuardDuty, Security Hub, VPC Flow Logs, DNS logging
• Evidence: trail configs, detector settings, log group definitions, alarm rules

SEC 5 — How do you protect your network resources?

• Look for: VPC segmentation, security groups, WAF, private subnets, VPC endpoints
• Evidence: VPC constructs, SG rules, WAF ACLs, endpoint definitions

SEC 6 — How do you protect your compute resources?

• Look for: patching, container scanning, runtime protection, minimal privileges
• Evidence: launch templates, task definitions, Lambda configs, scanning configs

SEC 7 — How do you classify your data?

• Look for: data classification tags, sensitivity labels, data catalog configs
• Evidence: resource tags, Macie configs, Glue catalog settings

SEC 8 — How do you protect your data at rest?

• Look for: encryption on ALL stores, KMS policies, key rotation
• Evidence: encryption properties on every storage resource in IaC

SEC 9 — How do you protect your data in transit?

• Look for: TLS 1.2+ enforcement, certificate management, HTTPS-only
• Evidence: listener configs, security policies, redirect rules

SEC 10 — How do you anticipate, respond to, and recover from incidents?

• Look for: response automation, forensic capabilities, containment procedures
• Evidence: remediation Lambdas, isolation procedures, backup configs

Step 8: Risk Assessment

For each finding, assess using Impact × Likelihood:

Impact: Minor (limited data exposure, no compliance violation) | Moderate (partial data exposure, minor compliance gap) | Severe (full data breach, regulatory violation, privilege escalation)

Likelihood: Low (requires chained exploits, strong compensating controls) | Medium (exploitable with moderate effort, partial controls) | High (easily exploitable, no compensating controls)

---STOP--- Checkpoint: Assessment complete — confirm findings before generating report.

Assessment summary:

• Critical findings: {count}
• High findings: {count}
• Medium/Low findings: {count}

Shall I produce the full security report, or would you like to discuss specific findings first?

Do NOT proceed past this point until the user explicitly confirms.

Step 9: Produce findings

# Security Assessment: {Workload Name}

## Executive Summary
- **Date**: {date}
- **Compliance Scope**: {frameworks}
- **Packages Analyzed**: {list}
- **Findings**: {X} Critical, {Y} High, {Z} Medium, {W} Low
- **Overall Security Posture**: {1-5} — {one-line justification}

## Security Scorecard
| Domain | Score (1-5) | Key Strength | Key Gap |
|--------|-------------|--------------|---------|
| Identity & Access | {score} | {strength} | {gap} |
| Data Protection (at rest) | {score} | {strength} | {gap} |
| Data Protection (in transit) | {score} | {strength} | {gap} |
| Network Protection | {score} | {strength} | {gap} |
| Compute Protection | {score} | {strength} | {gap} |
| Detection & Response | {score} | {strength} | {gap} |

## Critical and High Risk Findings
{For each: ID, domain, title, description, evidence (file:line), impact assessment, recommendation, effort, AWS services}

## Medium Risk Findings
{Same format, condensed}

## Low Risk Findings
{Summary table: ID | Domain | Title | Recommendation}

## Compliance Mapping
{If compliance requirements specified, map findings to relevant framework controls}
| Finding ID | SOC2 CC | HIPAA | PCI-DSS | Notes |
|------------|---------|-------|---------|-------|

## Prioritized Remediation Plan

### Quick Wins (< 1 week)
| Finding | Action | Impact | Effort |
|---------|--------|--------|--------|
{Enable encryption, tighten SG rules, rotate keys, fix TLS versions}

### Foundation (1-4 weeks)
| Finding | Action | Impact | Effort | Dependencies |
|---------|--------|--------|--------|--------------|
{Implement least privilege, add WAF, enable GuardDuty, add VPC endpoints}

### Strategic (1-3 months)
| Finding | Action | Impact | Effort | Dependencies |
|---------|--------|--------|--------|--------------|
{Zero-trust network, automated response, forensic capabilities, compliance program}

## Next Steps
{Top 5 concrete security actions the team should take this week}

Step 10: Offer follow-up

After delivering the assessment, offer:

Would you like me to:

• Design least-privilege IAM policies for specific roles?
• Generate IaC for security controls (GuardDuty, Security Hub, Config rules)?
• Create an incident response playbook for a specific threat?
• Map findings to a specific compliance framework in detail?
• Design network segmentation architecture?
• Tighten specific security group rules with minimal disruption?

Calibration Guidance

• A workload with encryption everywhere, least-privilege IAM, VPC segmentation, GuardDuty, and Security Hub is MATURE — focus on hardening, detection depth, and response automation
• Every finding MUST have code evidence — no "you should enable encryption" without first checking if it's already enabled
• Flag protocol-level risks explicitly: TLS < 1.2 is always Critical, weak ciphers always High
• If compliance is specified, map EVERY Critical/High finding to the relevant compliance control
• "Cannot Determine" is valid when static analysis is insufficient (e.g., actual IAM usage patterns require Access Analyzer data)
• Acknowledge strong security practices prominently before listing gaps