Has anyone tried automatically generating software docs from user session data?

Hi everyone,

I’ve spent years wrestling with outdated documentation and missing knowledge in various software products. Recently, I started experimenting with capturing user sessions (like clicks, screenshots, and flows) and automatically building documentation without human involvement.

The idea is this: if we can observe how people actually navigate and use a product, we can generate living documentation without any extra effort from developers or product teams.

Questions for the community:

1. Has anyone tried something similar or used a tool that does this?
2. What do you see as the biggest challenges or pitfalls with turning those sessions into a valuable knowledge base automatically?
3. Do you rely on any existing workflows, scripts, or libraries that keep your documentation up to date?

Specific challenge:

I’m struggling to build a unified "map" of the product from these user sessions. I call it an "island mapping" problem. Each session is like a navigation trace; in theory, they combine into one big map. With GPS, you can easily align traces, but user sessions don’t have a straightforward reference. I looked into analytics methods, but they might not work at this scope.

I’d love any thoughts or suggestions. Just trying to learn from others’ experiences. Thanks!