Agent Skills: Implementing Envelope Encryption with AWS KMS

Implementing Envelope Encryption with AWS KMS

Overview

Envelope encryption is a strategy where data is encrypted with a data encryption key (DEK), and the DEK itself is encrypted with a master key (KEK) managed by AWS KMS. This approach allows encrypting large volumes of data locally while keeping the master key secure in a hardware security module (HSM) managed by AWS. This skill covers implementing envelope encryption using AWS KMS GenerateDataKey API.

When to Use

• When deploying or configuring implementing envelope encryption with aws kms capabilities in your environment
• When establishing security controls aligned to compliance requirements
• When building or improving security architecture for this domain
• When conducting security assessments that require this implementation

Prerequisites

• Familiarity with cryptography concepts and tools
• Access to a test or lab environment for safe execution
• Python 3.8+ with required dependencies installed
• Appropriate authorization for any testing activities

Objectives

• Understand the envelope encryption pattern and its advantages
• Generate data encryption keys using AWS KMS GenerateDataKey
• Encrypt/decrypt data locally using DEKs
• Store encrypted DEK alongside ciphertext
• Implement key caching to reduce KMS API calls
• Handle key rotation with automatic re-encryption
• Implement multi-region encryption for disaster recovery

Key Concepts

Envelope Encryption Flow

1. Call kms:GenerateDataKey to get plaintext DEK + encrypted DEK
2. Use plaintext DEK to encrypt data locally (AES-256-GCM)
3. Store encrypted DEK alongside ciphertext
4. Discard plaintext DEK from memory
5. For decryption: call kms:Decrypt on encrypted DEK, then decrypt data

Advantages Over Direct KMS Encryption

| Aspect | Direct KMS | Envelope Encryption | |--------|-----------|-------------------| | Max data size | 4 KB | Unlimited | | Latency | Network round-trip per operation | Local encryption | | Cost | $0.03/10,000 requests | Fewer KMS requests | | Offline | Not possible | Yes (with cached DEKs) |

KMS Key Types

• AWS Managed: AWS creates and manages (aws/s3, aws/ebs)
• Customer Managed: You create and manage policies
• Custom Key Store: Backed by CloudHSM cluster

Security Considerations

• Never store plaintext DEK; only keep encrypted DEK
• Use key policies to restrict who can call GenerateDataKey and Decrypt
• Enable AWS CloudTrail logging for all KMS API calls
• Implement key rotation (automatic annual rotation for CMKs)
• Use encryption context for authenticated encryption metadata
• Handle KMS throttling with exponential backoff

Validation Criteria

• [ ] GenerateDataKey returns plaintext and encrypted DEK
• [ ] Data encrypts correctly with plaintext DEK using AES-256-GCM
• [ ] Encrypted DEK can be decrypted via KMS Decrypt API
• [ ] Decrypted DEK recovers the original data
• [ ] Plaintext DEK is wiped from memory after use
• [ ] Encryption context is validated during decryption
• [ ] Key rotation re-encrypts DEKs with new master key