Windows NT 4.0 was the first “proper” operating system I worked with in my IT career back in the late 1990s. Before that, I’d been supporting Windows for Workgroups , Windows 95 and 98 — but NT Workstation felt like stepping into the big leagues. It was stable, professional, and it left a real mark on me. Almost 30 years later, I wanted to revisit it and answer a simple question: What actually still works if you put Windows NT 4.0 on the Internet of 2025? In this video, I walk NT through the modern web using a QEMU virtual machine and a handful of tools that simply didn't exist when NT was released. I explore: • Internet Explorer 6 SP1 The newest browser NT can run — and how far it gets before modern HTTPS completely stops it. • Opera A more capable browser from the 2000s, including the installer issues, the manual MSI extraction trick, and whether it can render anything from today's web. • Text-based Internet services A look at Telnet on NT 4.0, and why the early Internet still functioned perfectly well without a web browser. • And finally… Outlook Express 6 vs modern Gmail Using Stunnel running on my Mac, NT connects via plain old POP3 while the Mac handles the encrypted TLS connection to Gmail. To my surprise, it actually works. NT 4.0 sends and receives mail with a 2025 Gmail account. This was a fascinating deep dive into a system that shaped the start of my IT career, and a reminder of just how far the Internet has evolved since 1996. 🔧 Tools used in this video QEMU: WebOne (HTTP/HTTPS Proxy): Stunnel: If you enjoyed this kind of historical/technical exploration, the channel looks at enterprise computing from the Windows NT era right through to the present day. Thanks for watching — and I’ll see you in the next video. Ta-ta! Windows NT 4.0, Windows NT4, Windows NT on modern internet, NT4 Internet Explorer 6, IE6 TLS, Opera Windows NT, Telnet Windows NT, Outlook Express 6 Gmail, Gmail POP3 legacy, Stunnel Gmail, WebOne proxy NT4, QEMU Windows NT 4.0, vintage computing, retro operating systems, 1990s enterprise IT, NT workstation internet, legacy OS networking, classic Windows experiment