Blog / Series
7-Part Series

Agentic Modernization

Building a Claude Code skill that orchestrates specialized AI agents to analyze legacy codebases and produce implementation-ready modernization blueprints — PRDs, user stories, and prompts for agentic coding assistants.

7
Parts
57
Min Total Read
3
Sample Apps
6
AI Agents
The Series
From legacy codebase to implementation-ready specs.
1

The Monolith Whisperer

Why we built an AI agent team for cloud modernization — and why the first agent just listens
Agentic approach, codebase scanner, read-only analysis 8 min read
2

Drawing Lines in the Mud

How an AI agent applies Domain-Driven Design to codebases that have never heard of it
Domain decomposition, event storming, Strangler Fig 9 min read
3

Designing the Target

An AI architect that picks AWS services based on what the code actually does
Serverless-first, cloud patterns, data architecture 8 min read
4

Security Is Not a Phase

Why the security agent runs in parallel with the architect — and what it keeps finding
Parallel security analysis, identity migration, defense in depth 8 min read
5

Eyes on the System

Designing observability and operational readiness for applications that have never been observed
SLOs, distributed tracing, CI/CD, chaos engineering 8 min read
6

The Money Talk

Real AWS pricing for real migrations — and the licensing math that gets projects funded
Three-tier cost modeling, TCO comparison, licensing savings 7 min read
7

The Handoff

How the final agent turns six reports into PRDs, user stories, and implementation prompts
PRD generation, user stories, prompts for AI coding agents 9 min read
Sample Applications
Three real codebases. Three different stacks.
ColdFusion
ColdFusion CMS

~1,800 files, custom ORM (FourQ), 15 years of organic growth, hand-rolled S3 client with hardcoded credentials. The classic "nobody who built this still works here" legacy system.

Java
Java E-Commerce Platform

Spring Boot 2.3, 45K files, Oracle database, 312 pseudo-microservices sharing a single DB. A distributed monolith — all the complexity of microservices, none of the benefits.

.NET
.NET Enterprise Portal

ASP.NET MVC on .NET Framework 4.8, SQL Server, Windows-specific dependencies (NTLM, COM interop, CLR stored procedures). The "works on Windows Server" migration challenge.

The Agent Team
Specialized agents, orchestrated in waves.
Wave 1
Codebase Scanner
→ discovery.md
Wave 2
Domain Decomposer
→ decomposition.md
Wave 3
Solution Architect Security Architect
→ architecture.md + security.md
Wave 4
Observability Architect Cost Analyzer
→ observability.md + cost.md
Wave 5
Migration Strategist
→ PRD + User Stories + Prompts

"Organizations don't need more AI tools —
they need a guide."

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