AiLive! 2-Day Hands-On Training Workshop: Modernizing Legacy .NET Applications with AI Coding Agents
January 28-29, 2027 | Live Virtual Training
Level: Intermediate
In this intensive two-day hands-on seminar/workshop, attendees will take a realistic legacy .NET application through a repeatable enterprise modernization workflow.
The starting solution is a deliberately imperfect .NET Framework application with multiple projects, SQL Server dependencies, outdated packages, legacy configuration patterns, limited automated tests, security concerns, manual deployment processes, and minimal observability.
Rather than immediately changing code, attendees will first establish a working baseline, use AI-assisted engineering techniques to explore the application, reconstruct its architecture and business behavior, identify dependencies and technical debt, and build a modernization assessment.
They will then create a test safety net and evaluate which application components should be retained, upgraded, refactored, replatformed, replaced, or deliberately left unchanged.
On Day 2, attendees will modernize selected components toward .NET 10 LTS, improve configuration and security, establish automated quality gates, deploy the modernized application to a pre-provisioned Azure environment, and add production observability.
Throughout the workshop, attendees will use AI coding agents to accelerate engineering tasks while applying explicit validation, testing, code review, and human approval checkpoints.
The goal is not to demonstrate a one-click migration. The goal is to provide a practical and repeatable modernization methodology that teams can apply to real enterprise applications.
What You Will Learn
By the end of this seminar/workshop, attendees will be able to:
- Assess a legacy .NET Framework solution and create an inventory of projects, dependencies, integrations, technical debt, security concerns, and modernization risks.
- Build characterization, unit, integration, and API tests that establish a behavioral safety net before making significant modernization changes.
- Evaluate and document whether application components should be retained, upgraded, refactored, replatformed, replaced, or retired based on business and technical requirements.
- Modernize and validate selected components toward .NET 10 LTS using AI coding agents while enforcing build, test, security, code-review, and human-approval gates.
- Deploy and evaluate a modernized application in Azure using secure identity, automated delivery checks, OpenTelemetry-based observability, and a production-readiness checklist.
Day 01
Discover → Understand → Assess → Protect → Decide → Plan
Day 1 focuses on understanding and protecting the application before making significant changes.
Attendees will:
- Establish a known working baseline for the legacy application.
- Configure AI coding-agent instructions and engineering guardrails.
- Use AI-assisted analysis to explore unfamiliar projects, dependencies, entry points, integrations, configuration, and business workflows.
- Reconstruct the application's architecture and identify areas of technical debt and modernization risk.
- Review outdated and incompatible dependencies.
- Identify security, configuration, data-access, and deployment concerns.
- Create characterization and regression tests around business-critical behavior.
- Add targeted unit, integration, and API tests to strengthen the modernization safety net.
- Evaluate modernization options including retain, upgrade, refactor, replatform, replace, and retire.
- Compare monolith, modular-monolith, service decomposition, cloud, hybrid, and container strategies without assuming every workload requires the same architecture.
- Document key decisions using a modernization decision matrix and Architecture Decision Records.
- Build a prioritized modernization backlog with clear acceptance criteria and validation checkpoints.
Day 1 Deliverables:
- Application architecture and dependency inventory
- Modernization assessment
- Risk and technical-debt analysis
- Automated test safety net
- Modernization decision matrix
- Architecture Decision Records
- Prioritized modernization backlog
- AI coding-agent instructions and engineering guardrails
Day 02
Modernize → Secure → Validate → Deploy → Observe → Operate
Day 2 uses the decisions and safety net created on Day 1 to modernize selected parts of the application.
Attendees will:
- Execute a targeted modernization of selected application components toward .NET 10 LTS.
- Review AI-generated migration plans and proposed code changes before accepting them.
- Resolve representative framework, dependency, configuration, and compatibility issues.
- Modernize selected configuration and data-access patterns.
- Improve dependency security and review authentication and authorization concerns.
- Replace embedded secrets and legacy credential patterns with secure configuration and managed identity where appropriate.
- Introduce automated build, test, dependency, and security quality gates.
- Use AI-assisted code review to identify potential regressions and modernization risks.
- Deploy the modernized application to a pre-provisioned Azure environment using Azure App Service and Azure SQL.
- Configure secure application-to-database connectivity using managed identity.
- Add logging, metrics, distributed tracing, diagnostics, and health signals using OpenTelemetry and Azure Monitor/Application Insights.
- Perform a production-readiness review covering functionality, security, deployment, rollback, monitoring, operational ownership, and supportability.
Day 2 Deliverables:
- Modernized .NET 10 reference implementation
- Automated quality gates
- Security improvements
- Azure deployment
- Managed identity configuration
- OpenTelemetry-based observability
- Production-readiness assessment
- Completed enterprise modernization playbook
What You Will Take Back to Work
Attendees will leave with reusable artifacts that can be adapted to real modernization projects, including:
- A repeatable enterprise application modernization methodology
- Legacy and modernized reference application repositories
- Modernization assessment template
- Application inventory and dependency-analysis template
- Modernization decision matrix
- Architecture Decision Record templates
- Characterization and regression testing patterns
- AI coding-agent instructions and engineering guardrails
- AI-assisted engineering workflow examples for discovery, testing, modernization, review, and validation
- Modernization backlog template
- CI/CD and automated quality-gate examples
- Azure deployment reference architecture
- Security and managed-identity patterns
- OpenTelemetry and Azure Monitor observability examples
- Production-readiness checklist
- Enterprise modernization playbook
- A practical framework for selecting the first application and modernization workload to tackle after the workshop
Prerequisites
Attendees should be comfortable reading and modifying C# code and should have working familiarity with:
- C# and .NET development
- Visual Studio
- Web applications and APIs
- Relational database concepts
- Basic Git workflows
Prior experience with GitHub Copilot, Claude Code, Codex, or other AI coding agents is not required.
Prior Azure experience is helpful but not required. The workshop focuses on the modernization workflow rather than teaching Azure administration from scratch.
This is a hands-on engineering workshop rather than an introductory .NET course. Attendees should already be able to navigate an existing .NET solution, read C# code, understand basic application architecture, and work with Git.
Advanced modernization, architecture, and production-readiness concepts will be introduced progressively throughout the workshop.
Recommended Lab Environment
Attendees should bring a Windows or Mac development laptop with:
- Windows 11 recommended
- Local administrator access
- Current supported version of Visual Studio 2026
- Required .NET development workloads
- .NET 10 SDK
- Git
- GitHub account
- Access to at least one supported AI coding agent such as GitHub Copilot, Claude Code, or Codex
- Web browser with access to GitHub and Azure
- Ability to clone and work with Git repositories
The workshop will provide:
- A prebuilt legacy .NET application repository
- Known-good checkpoint branches for every major lab
- Completed reference implementation
- Pre-provisioned Azure lab environments
- Azure App Service resources
- Azure SQL resources
- Required identity and access configuration
- Lab instructions and troubleshooting checkpoints
Docker Desktop and a local SQL Server installation are not required.
The lab design includes recovery checkpoints so attendees who encounter an AI-generated code issue, configuration problem, or incomplete lab can restore a known-good state and rejoin the workshop without restarting the entire exercise.