Serving from the Dark Side: When (and Why) Windows + IIS Still Make Sense

:brick: Hosting on Windows Server and IIS: Why Do People Actually Do This?

Understanding the Other Side of the Web Stack
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:bullseye: Introduction

While the Linux crowd is busy fine-tuning nginx.conf files and restarting Apache for the tenth time, there’s a parallel universe where developers are deploying websites with a few clicks in IIS Manager. If you’re a die-hard Linux user, this might sound like madness — but for some, it’s the method behind the madness.

This guide covers why some teams and companies still use Windows Server and IIS (Internet Information Services) in 2025, what benefits it brings (yes, there are some), and the tradeoffs that come with it.


:brain: What Is IIS, and Why Is It Even Still a Thing?

IIS is Microsoft’s web server. It’s been part of Windows Server since the ’90s and comes preinstalled or easily added via Roles and Features. It supports HTTP, HTTPS, FTP, FTPS, SMTP, and more.

It’s not just for hobbyists — large-scale enterprise apps, legacy systems, and .NET-based environments often rely on IIS.


:white_check_mark: Why Someone Might Choose IIS over Apache or NGINX

  • Tight integration with .NET and ASP.NET
    • Built-in support for C#, Razor pages, and .NET Framework/6/7+ apps.
  • GUI Management
    • IIS Manager offers a visual way to configure websites, bindings, SSL, MIME types, and more.
  • Windows Authentication and Active Directory
    • Easily tie web authentication into a company’s existing AD.
  • Ease of Use for Windows Admins
    • If your team already manages AD, Exchange, and SQL Server — IIS fits like a glove.
  • Built-in Tools
    • Application Pools, Request Filtering, Logging, IP restrictions — all with checkbox simplicity.

:cross_mark: Downsides of Using Windows Server + IIS

  • Resource Intensive
    • Heavier RAM/CPU usage compared to nginx or Apache.
  • Licensing Costs
    • Requires Windows Server licenses; not ideal for budget-conscious devs.
  • Command Line? What’s That?
    • Scripting automation is possible (via PowerShell), but most tasks are done via GUI.
  • Less Open-Source Support
    • Most modern web tools assume a Linux-based stack.

:thinking: When Does It Make Sense?

  • You’re Running Enterprise .NET Apps
  • You’re Hosting on Windows Anyway (Exchange, AD, MSSQL — might as well add IIS)
  • You Want GUI Simplicity Over Terminal Control
  • You Need Windows Authentication or NTFS-level permissions tied into the stack

:test_tube: Example Scenario

You’re building a C# web app using ASP.NET Core. Your infrastructure is already Microsoft-based. You:

  1. Install Windows Server 2022.
  2. Add the IIS role.
  3. Publish your app to a folder.
  4. Point IIS at it.
  5. Bind to a domain and add SSL via GUI.

Done. No reverse proxy config. No messing with Certbot. It just works (in a Microsoft sort of way).


:hammer_and_wrench: Tools and Alternatives

  • PowerShell for Automation
  • Web Deploy for pushing .NET apps
  • IIS Crypto for managing security protocols and cipher suites
  • IIS Manager for Remote Administration

:puzzle_piece: Final Thoughts

IIS and Windows Server aren’t dead — they’re just a different beast. If you’re all-in on Linux, you can skip it. But if your work touches enterprise environments, knowing your way around IIS is still a valuable skill.

No, you don’t have to like it. But knowing it could be the edge that lands you a consulting gig or helps you fix a misconfigured site when no one else on the team wants to touch the blue box.


:brain: Want More Windows Server Content?

By day, I work deep in the Microsoft stack — Windows Server, IIS, Active Directory, the whole enterprise toolkit.

By night, I’m all Linux and macOS — because sanity matters.

If you want deeper dives into managing IIS, scripting with PowerShell, automating Windows tasks, or just surviving in a corporate environment that still uses Internet Explorer (kidding… hopefully), let me know.

I’ve got real-world experience — and the scars to prove it.


:megaphone: Got Opinions?

If you’ve had to host on IIS and lived to tell the tale, share your experience below. Bonus points for war stories, PowerShell hacks, or tales of migration to Apache/nginx.


Disclaimer: This guide is based on real-world usage and observation, not vendor marketing. No affiliate links, no fluff — just facts and experience from both sides of the stack.