Overview

We are looking for an experienced DevOps / Platform Engineer with strong expertise in on-premises Windows Server/IIS and Microsoft Azure environments.

The client currently hosts its applications on Windows/IIS servers and is progressively migrating workloads to Azure. The engineer will own the delivery platform for both environments, ensuring reliable, automated, and zero/near-zero-downtime deployments.

The role requires building and maintaining CI/CD pipelines where the same versioned artifacts can be deployed to either on-prem IIS or Azure App Service, with environment-specific configuration and secrets injected during deployment.

Key Responsibilities

• Own and maintain CI/CD pipelines for deploying .NET 10 services and React SPA applications to on-premises Windows/IIS servers.
• Build deployment pipelines using self-hosted build agents, deployment groups, or runners operating within restricted corporate networks.
• Manage and administer IIS hosting for ASP.NET Core applications, including:
  • ASP.NET Core Hosting Bundle
  • Application Pools
  • Websites and bindings
  • SSL/TLS certificates
  • In-process vs. out-of-process hosting
  • web.config
  • Environment-specific configuration
• Design and implement zero-downtime / near-zero-downtime releases for on-prem IIS environments.
• Implement blue-green or side-by-side deployment strategies using separate sites/app pools behind ARR or a load balancer.
• Configure application health checks, traffic switching, rollback mechanisms, and release validation.
• Avoid deployment approaches that cause unnecessary application outages, including dependency on appoffline.htm.
• Automate Windows/IIS server configuration using:
  • PowerShell
  • WebAdministration / IISAdministration
  • WinRM
  • Web Deploy (MSDeploy)
  • DSC where applicable
• Ensure Windows/IIS environments are reproducible and automated rather than manually configured.
• Implement a build-once, deploy-many model where the same versioned artifact can be deployed to IIS or Azure App Service.
• Manage environment-specific configuration, application settings, and secrets at deployment/release time.
• Handle on-premises secrets and credentials, where Azure Managed Identity is not available.
• Coordinate database deployment and migration processes for on-premises SQL Server and PostgreSQL, with appropriate validation and rollback controls.
• Support the migration of applications from on-premises IIS to Azure App Service.
• Plan and execute migration activities including:
  • Environment parity testing
  • Application validation
  • DNS changes
  • Traffic cutover
  • Monitoring
  • Rollback planning
• Troubleshoot deployment, IIS, Windows Server, application hosting, networking, and pipeline issues.
• Collaborate with development, QA, infrastructure, and application teams to ensure reliable application delivery.

Required Skills

• 6+ years of overall DevOps / Platform Engineering experience.
• 3+ years of hands-on experience deploying .NET applications to on-premises Windows Server/IIS through automated CI/CD pipelines, not manual copy-and-paste deployments.
• Strong hands-on experience with IIS administration, including:
  • Application Pools
  • Site bindings
  • SSL certificates
  • URL Rewrite
  • ARR
  • ASP.NET Core Hosting Bundle
  • web.config
• Strong experience with Microsoft Azure, particularly Azure App Service and deployment automation.
• Hands-on experience with self-hosted agents/runners such as:
  • Azure DevOps Self-Hosted Agents
  • Azure DevOps Deployment Groups
  • GitHub Self-Hosted Runners
• Experience operating CI/CD agents within restricted corporate networks / behind firewalls.
• Advanced PowerShell scripting and automation skills.
• Hands-on experience with WinRM and Web Deploy (MSDeploy).
• Experience implementing zero-downtime or near-zero-downtime IIS deployments behind a load balancer.
• Strong understanding of CI/CD, release management, artifact management, rollback, and deployment strategies.
• Experience working with Windows Server environments and application hosting.
• Good understanding of configuration and secrets management across different environments.
• Experience with SQL Server and/or PostgreSQL deployment/migration processes.

Preferred Skills

• Experience migrating applications from on-premises IIS to Azure App Service.
• Hands-on experience with Azure Arc.
• Experience with hybrid monitoring of on-premises servers using Azure Monitor.
• Experience with load balancers such as:
  • F5
  • NetScaler
  • Windows NLB
• Experience with Azure DevOps or GitHub Actions.
• Experience with Infrastructure as Code / configuration management, including DSC.
• Experience with OpenTelemetry in on-premises environments.
• Knowledge of:
  • Windows Event Logs
  • Windows Performance Counters
  • OpenTelemetry Collector
  • Hybrid observability
• Experience forwarding telemetry from restricted on-premises networks to centralized monitoring platforms.

Qualifications

• Experience: 6+ Years
• Shift: 2pm to 11 pm
• Location: Remote
• Employment Type: Contract

Technical Environment

• Application: .NET 10 / ASP.NET Core / React SPA
• On-Prem: Windows Server / IIS
• Cloud: Microsoft Azure / Azure App Service
• CI/CD: Azure DevOps / GitHub Actions
• Automation: PowerShell / WinRM / MSDeploy / DSC
• Load Balancing: ARR / F5 / NetScaler / Windows NLB
• Databases: SQL Server / PostgreSQL
• Monitoring: Windows Event Log / Performance Counters / OpenTelemetry / Azure Monitor

Interview Focus Areas

1. On-Premises Zero-Downtime Deployment
   • Design a CI/CD pipeline that deploys an ASP.NET Core application to three IIS servers behind a load balancer, ensuring zero/near-zero downtime. Explain:
     • Deployment sequence
     • Health checks
     • Traffic draining/switching
     • Blue-green or side-by-side deployment
     • Configuration management
     • Rollback strategy
     • Certificate and IIS considerations
2. Hybrid Build-Once Deployment Model
   • Explain how you would design one CI/CD pipeline and one versioned artifact that can deploy the same application to both:
     • On-premises IIS
     • Azure App Service
   • Explain how you would handle:
     • Environment-specific configuration
     • Secrets
     • Connection strings
     • Deployment slots
     • IIS configuration
     • Rollback
3. IIS & PowerShell Automation
   • Explain how you would automate IIS site/application-pool creation, bindings, certificates, application deployment, configuration changes, and validation using PowerShell, WebAdministration/IISAdministration, WinRM, and MSDeploy.
4. On-Premises to Azure Migration
   • Explain your approach for migrating an existing IIS-hosted application to Azure App Service, including parity testing, database connectivity, configuration/secrets, DNS, traffic cutover, monitoring, and rollback.

Ideal Candidate Profile

The ideal candidate is a hands-on DevOps / Platform Engineer who has significant real-world experience managing Windows/IIS-based .NET applications in production, rather than someone whose experience is limited to cloud-only DevOps.

Strong practical experience with IIS, PowerShell, Windows Server, CI/CD, self-hosted agents, load balancers, zero-downtime deployments, and Azure App Service migration is essential.