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…
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
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 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 3.1. You can check it out here and learn more about what it was like to build it: https://www.dialup.net/wingpt/
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