WinGPT – AI assistant for Windows 3.1
Hey HN, I didn't want my Gateway 4DX2-66 from 1993 to be left out of the AI revolution, so I built an AI Assistant for Windows 3.1, based on the OpenAI API. The most interesting parts of building this were: - Getting TLS 1.2 and 1.3 working on Windows 3.1 so that WinGPT could directly connect to OpenAI's server without relying on a modern machine for TLS termination. - Learning about the memory segmentation architecture on 16-bit Windows, including the difference between far and near pointers. - Building the UI in plain C code with the Windows API and limited selection of controls in Windows…
WinGPT – AI assistant for Windows 3.1 launched on June 25, 2023 with 382 votes, #52 of 4,655 launches that month and more than 99% of that year's launches. The site was still online in September 2026, 3 years on.
In plain words
WinGPT is an AI assistant for Windows 3.1 that connects to the OpenAI API, allowing users with vintage 1990s machines to access AI capabilities on their legacy systems. Built in C with the Windows API, it implements TLS 1.2 and 1.3 support to communicate directly with modern servers without requiring a proxy. The software demonstrates novel solutions to memory segmentation challenges inherent in 16-bit Windows architecture.
written from the facts on this page · September 2026
From the sources
Do you use Windows 3.1? Do your friends send you jokes and haikus written by ChatGPT, and make you feel left out? Do you wish you had the sum of all human knowledge at your fingertips? Or wish you had your very own AI chatbot on your trusty 386? Wish no more! Introducing WinGPT, an AI Assistant for Windows 3.1. WinGPT is written in C, using the standard Windows API. I used Open Watcom v2 as the compiler, which is very convenient as it supports cross-compiling to 16-bit Windows from even Windows 11. WinGPT connects to the OpenAI API server natively with TLS 1.3 , so it doesn't require a proxy on a modern machine to terminate TLS. To see how I did this and some of the challenges, take a look…from dialup.net
In the maker’s words, at launch
Hey HN, I didn't want my Gateway 4DX2-66 from 1993 to be left out of the AI revolution, so I built an AI Assistant for Windows 3.1, based on the OpenAI API. The most interesting parts of building this were: - Getting TLS 1.2 and 1.3 working on Windows 3.1 so that WinGPT could directly connect to OpenAI's server…
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