I'm not sure I've seen any good vendors but I remember seeing a reverse devops tool posted a few days ago that would reverse engineer your VMs into Ansible code. If that got extended to your entire environment, that would almost be an auto documenting process.

All of those endpoints should be documented in an environment variable or similar as well.

The breakdown is when you don't instrument the same tooling everywhere.

Documentation is generally out of date by the time you finish writing it so I don't really bother with much detail there.

You then eventually have that same pattern happen with services, where people give up on mapping the full thing out as well.

What I've done for my current team is to list the "downstream" services, what we use them for, who to contact, etc. It only goes one level deep, but it's something that someone can read quickly during an incident.

A laptop computer is extremely complex, but is actively developed and maintained by a small number of people, built on parts themselves developed by a small number of people, many of which are themselves built on parts themselves developed by a small number of people, and so on and so forth.

This works well in electronics design, because everything is documented and tested to comply with the documentation. You'd think this would slow things down, but developing a new generation of a laptop takes fewer man hours and less calendar time than developing a new generation of any software of a similar complexity running on it, despite the laptop skirting with the limitations of physics. Technical debt adds up really fast.

The top-level designers only have access to what the component manufacturers have published, and not to their internal designs, but that doesn't matter because the publications include correct and relevant data. When the component manufacturer comes out with something new, they use documentation from their supplier, to design the new product.

As long as each components of documentation is complete and accurate, it will meet all of the needs of anyone using that component. Diving deeper would only be necessary if something is incomplete or inaccurate.

You’re describing the infrastructure of a large system — it’s a custom-built machine designed to serve a custom purpose. There are no examples in the world of things like that working without a lot of human intervention.

This is compounded, as you say, by increasing demands placed on the system: “Now it must react to AIs committing code,” or “Our customer base is growing but your Ops budget is decreasing.” This means the system needs more humans, not fewer.

It feels a bit dishonest to be asking for advice on how to tackle the complexity problem for SREs when you're are actually providing a paid solution for the very same problem.

The biggest issue isn't just that documentation gets outdated; it's that the 'mental model' of the system only exists accurately in a few engineers' heads at any given moment. When they leave or rotate, that model degrades.

We found the only way to really fight this is to make the system self-documenting in a semantic way—not just auto-generated docs, but maintaining a live graph of dependencies and logic that can be queried. If the 'map' of the territory isn't generated from the territory automatically, it will always drift. Manual updates are a losing battle.

2. Systems should be explicit, not implicit. Configuration should be explicit wherever possible. Implicit behavior should be documented.

3. Living documentation adjacent to your systems. Write markdown files next to your code. If you keep systems documentation somewhere else (like some wysiwyg knowledge system bullshit) then you must build a markdown-to-whatever sync job (where the results are immutable) else the documentation is immediately out of date, and out of date documentation is just harmful noise.

4. If it's dead, delete it. You have version control for a reason. Don't keep cruft around. If there's a subnet that isn't being used, delete it.

Lastly, if you find yourself in this situation and have none of the above, ask yourself if you really have the agency to fix it -- and I mean really fix it, no half measures -- then do so. If you don't, then your options are to stop caring or find a new job. The alternative is a recipe for burnout.

Beyond a certain scale, you can't keep a mental model of the entire system in your head. What matters then is accessing accurate, up to date information the moment you need it (troubleshooting an unfamiliar subsystem, making a cross-cutting change). Table stakes are IaC, APM, structured logging.

Code-generated docs sound great in theory, but a huge category of knowledge never lives in code (RFCs, deployment processes, how to get prod access). Humans have to write and maintain those. That requires a culture where people believe their effort matters (and ideally gets rewarded). Without that, docs rot regardless of tooling.

Then there's discovery. The docs often exist; they're just buried. RAG tools actually help here imo. When people can find what you wrote, you're more motivated to keep it accurate. As we increasingly rely on agents to tell us about our system, we're going to have to ensure the docs they're reading are not woefully out of date or inaccurate.