AI-Powered Architecture Discovery for a Legacy Monolith

A safe, downtime-free modernization of a mission-critical monolith mobile app through AI-assisted architecture discovery to reveal dependencies and design an incremental, audit-friendly roadmap.

AI-Powered Architecture Discovery for a Legacy Monolith

About the client

A US-based insurance company with a multi-state policy portfolio needed to revamp its legacy mobile app to boost customer loyalty and streamline the settlement process.

About

the Product:

An enterprise-grade policy administration and claims platform serving multiple lines (auto, property, liability, etc.) needed a revamp to improve performance, reduce operating expenses, and boost user experience.

Since major modules included quotes, underwriting, endorsements, billing, collections, loss notices, indemnification, and subrogation, we needed to map dependencies within the app and workflow to ensure the smooth, secure transition.

The app core is represented by a tightly coupled monolith with embedded ratings, rules, document generation, and batch jobs for nightly bordereaux, commissions, and compliance reporting. Also, there were connections to payment gateways, credit bureaus, third-party data providers, and regulatory e-filing.

Introduction:

Recommended by industry experts, the client sought to eliminate operational pain points, opaque dependencies, manual handoffs, and fragile CI/CD. Devox Software’s team got to work, making a zero-downtime, evidence-driven modernization kit.

Project

Team:

The team roles were flexibly distributed according to the project phase and involved a Delivery Manager, a Solution Architect, a Senior Backend Engineer, a Data and ML Engineer, a DevOps Engineer, a QA Engineer, and a Business Analyst with experience in InsurTech.

Challenges:

The project showed the most common difficulties when trying to upgrade a legacy app:

  • State-by-State Regulatory Variability. Different states enforced different reporting requirements, policy rules, audit standards, and compliance procedures. This complicated modernization because even a small re-architecture could affect downstream compliance logic.
  • Actuarial Dependency Risks. Rating engines, underwriting logic, and scoring models required actuarial validation and business approval before changes could be introduced into production.
  • External System Coupling. Critical workflows depended on external reinsurers, regulatory services, payment providers, and reporting systems. Many integrations lacked centralized ownership or clear operational visibility. 
  • Technical Limitations. Sparse documentation, tight coupling across policy, billing, claims, and reporting services, brittle CI/CD; inconsistent data contracts; mixed tech generations, and more.

Tech

Stack:

Area Before Modernization After Modernization
Backend Architecture Large tightly coupled .NET Framework monolith Modular .NET 8 services
Application Framework ASP.NET MVC + legacy service layers ASP.NET Core
Infrastructure Traditional VM-based hosting with manual scaling Azure AKS (Kubernetes) with containerized workloads
Deployment Model Manual and fragile CI/CD pipelines Azure DevOps automated CI/CD with canary deployments
Observability Fragmented logs and limited monitoring OpenTelemetry + Grafana unified observability
Runtime Visibility Minimal distributed tracing End-to-end distributed tracing and telemetry correlation
Integration Layer Direct synchronous integrations Kafka-driven event-ready integration architecture
Database Architecture Shared tightly coupled relational database PostgreSQL with domain-oriented decomposition planning
Caching Localized in-memory caching Redis distributed caching
Infrastructure Management  Manual infrastructure provisioning  Terraform Infrastructure as Code

Solution

How AI Mapped the Monolith:

Instead of starting with manual reverse engineering, Devox Software designed an AI-assisted architecture discovery pipeline that combined static analysis, runtime telemetry, and LLM-powered semantic interpretation.

Phase 1. Static Code & Dependency Analysis

We first ingested source code repositories, SQL scripts, CI/CD configurations, infrastructure manifests, and deployment pipelines.

The system then analyzed call graphs, database relationships, service interactions, event flows, and shared dependency chains.

This revealed hidden coupling between policy, claims, billing, and reporting domains.

Phase 2. LLM-Assisted Semantic Understanding

To understand undocumented business logic, we applied LLM-assisted semantic analysis across legacy service methods, stored procedures, batch jobs, and integration adapters to classify domain responsibilities, identify duplicated logic, detect anti-patterns, and generate contextual architectural documentation.

This significantly accelerated dependency discovery compared to manual analysis alone.

Phase 3. Runtime Correlation with Observability Data

Static analysis alone was insufficient because many real production flows differed from repository assumptions. To solve this, we correlated legacy architecture data with OpenTelemetry traces, distributed transaction telemetry, infrastructure metrics, and production traffic patterns visualized in Grafana.

This allowed us to identify actual runtime bottlenecks and critical user journeys affecting claims processing.

Modernization Strategy

Based on the AI-generated architecture map, Devox Software designed a phased strangler-fig modernization roadmap.The approach focused on extracting low-risk domains first and gradually shifting workloads into modernized services. This way, the modernization pipeline included:

  • canary releases
  • automated rollback
  • pre-flight validation
  • infrastructure-as-code standardization
  • and progressive traffic shifting inside Azure AKS

This minimized operational risk while preserving business continuity.

“One of the most important engineering decisions was choosing incremental modernization over a full rewrite. While a complete rebuild could theoretically simplify architecture faster, it introduced unacceptable operational and regulatory risk,” said Alex Kukarenko, Director of Legacy Systems Modernization at Devox Software.

Trade-Offs:

Engineering Decision Why We Chose It Trade-Off
Incremental Decomposition vs Full Rewrite We prioritized gradual domain extraction and controlled modernization instead of replacing the entire platform at once Slower short-term transformation in exchange for significantly lower operational and regulatory risk
Shared Database Transition vs Immediate Database Split Several shared data contracts were temporarily preserved to avoid breaking tightly coupled insurance workflows Introduced temporary architectural complexity during the transition period
Runtime Observability First vs Immediate Refactoring We invested early in OpenTelemetry instrumentation, distributed tracing, and production telemetry visibility before rewriting services Delayed aggressive feature refactoring during early modernization phases
AI-Assisted Discovery vs Manual Reverse Engineering We combined static analysis with LLM-powered semantic code understanding to accelerate dependency mapping Required additional AI validation and architecture review by senior engineers
Event-Driven Integration Planning vs Synchronous Coupling Kafka-based event-driven patterns were introduced gradually instead of maintaining direct synchronous dependencies Increased integration planning complexity during transition
Infrastructure-as-Code vs Manual Provisioning Terraform-based infrastructure management replaced manually configured environments Required upfront environment codification and governance alignment

Results:

We’ve created a comprehensive app architecture mapping to prepare for further modernization steps. This way, the client has received the following outcomes:

  • Accelerated dependency discovery and migration planning by approximately 45%
  • Reduced Sev-1 incidents during deployments by nearly 60%
  • Improved incident investigation speed by up to 70% through OpenTelemetry distributed tracing
  • Enabled rollback validation and canary releases with under 5-minute rollback readiness
  • Reduced manual dependency analysis and architecture reverse-engineering effort by approximately 50%
  • Built a domain-oriented modernization roadmap supporting phased migration to AKS and event-driven services

As a result, the following modernization has been carried out without downtime.

Sum Up:

Outcome Impact
Modernization planning speed Accelerated dependency discovery and migration planning by approximately 45%
Release stability Reduced Sev-1 incidents during deployments by nearly 60%
Root-cause analysis Improved incident investigation speed by up to 70% through OpenTelemetry distributed tracing
Deployment confidence Enabled rollback validation and canary releases with under 5-minute rollback readiness
Operational continuity Completed modernization preparation and phased rollout with zero unplanned downtime
Architecture visibility Mapped hundreds of hidden service and database dependencies for insurance software development
Compliance readiness Established audit-friendly observability and deployment traceability across regulated flows
Engineering efficiency Reduced manual dependency analysis and architecture reverse-engineering effort by approximately 50%
Production observability Unified metrics, logs, and traces across infrastructure and application layers through Grafana and OpenTelemetry
Future modernization readiness Built a domain-oriented modernization roadmap supporting phased migration to AKS and event-driven services

Combining AI-driven monolith modernization with human experience, we’ve paved the way for safe modernization and aligned engineering with compliance, streamlining all timelines and saving budget for the transition. Consequently, the client had a chance to execute it with predictable risk and expected effects.

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