Michiel van Oudheusden discusses strategies for deploying web applications to multiple IIS servers using GitHub Actions and AWS, offering insights into scalable and maintainable CI/CD workflows for traditional architectures.

Overview

In this article, Michiel van Oudheusden dives into the practicalities of deploying web applications to traditional Windows servers running IIS within AWS infrastructure. Despite the prevalence of modern containerized deployments, many organizations continue to operate on established architectures, presenting unique deployment challenges.

Problem Statement

When migrating to the cloud, Michiel’s team needed to deploy the same web application across multiple IIS servers behind an AWS load balancer. The task required a CI/CD process that could dynamically target and update each server in a sustainable, automated fashion—all using GitHub Actions.

Key Topics Covered

  • Legacy Environments in the Cloud: Examination of why some enterprises still use IIS on Windows servers in cloud environments for critical workloads, favoring stability and familiarity over rapid adoption of containers or Kubernetes.
  • Deployment Challenges: Details on deploying consistently to a fleet of IIS servers behind load balancers, including scalability and configuration management hurdles.
  • GitHub Actions for Windows Deployments: Strategies and best practices for building dynamic GitHub Actions workflows that can handle deployments across multiple, possibly ephemeral, Windows machines.
  • Self-Hosted Runners: Exploration of using self-hosted GitHub Actions runners within an enterprise environment to interface directly with each IIS server, overcoming some restrictions associated with Microsoft’s hosted runners.
  • Maintenance and Scalability: Insights into maintaining such a deployment pipeline, including tips for scaling and minimizing manual intervention despite the underlying architecture’s legacy nature.

Conclusion

The article provides actionable insights for practitioners tasked with bridging modern CI/CD automation capabilities (like GitHub Actions) with legacy on-premise or cloud-based server environments, especially where containerization is not yet viable.

This post appeared first on Michiel van Oudheusden’s Blog. Read the entire article here