This speaks to the general problem with using LLMs for writing. The audience they are writing for us you, but you're trying to write for a totally different audience. In code, this manifests as comments in the code that are hyperspecific to the conversation you are having, and not the long term benefit of having those comments in the code.

I see this in docs a lot. I've been reading a lot of docs these days where it feels like the LLM is trying to hype up the person writing the docs. It's like it has no conception that the writing is meant for a 3rd party audience.

This!

Claude writes comments about how things used to work, which can be useful sometimes, especially if it's a big change that requires one to genuinely consider legacy behavior, but most of the time it shouldn't be there.

Two other somewhat related things it does:

- It writes as if someone reading the code and comments is aware of everything it is aware of (the current conversation, the code it has just looked at). It's really hard to make it understand that things need to stand on their own. A trick is to get a subagent to look at it with a fresh context, but it doesn't tremendously help

- It does all of this with user-facing strings too. Claude loves to write up tooltips and other labels that leak everything to the end user. Every single concern we have, every edge case we've meticulously made our code handle, it passes on to the user, so they don't "need to worry". But no sane user would think of these things. For them, a feature is a feature. The "dynamic scheduling" button should state what dynamic scheduling does plainly, and every edge case is handled by us. The "add" button does not need a label letting the user know that they will later be able to click the "delete" button, because the user will just realize it due to our adherence to proper design. Claude fails to understand good UX for the user cannot be replaced with endless labels and explanations.

It's an uphill battle and all attempts at solving this (or the brain-dead way new Anthropic models write) usually fail to work with me.

And will reference transient working docs in code comments.

// No retry was added here per AC 37b in FEATURE.MD.

Presumably you're not just blindly copying down what Claude copies out for you, but actually reading, interpreting, and understanding it for yourself?

I struggled with this for a long time, but actually seem to have gotten to a place where this is largely resolved. Copy/paste from my current claude.md:

The CC-5 rule specifically seems to be (just from reading through, nothing repeatable-eval based) the part that actually catches and prevents me from having to clean it up afterwards.

```

### Code comments

The failure this prevents: writing a comment that narrates the change I am making right now. That context is real, but it expires the instant the change merges — the defect it describes no longer exists, so the comment becomes a story about a problem no future reader can observe. It is a changelog entry in the wrong file, and a third copy of text already required in the commit body (3.b) and the PR description.

- *CC-1 (MUST NOT)* Write a comment describing a change, a fix, a defect, its cause, or what the code used to do. No "was/now/previously/instead of", no "this fixes", no "needed because otherwise", no "note that we no longer".

- *CC-2 (MUST)* Apply the survival test to every comment before writing it: would this still be true and useful to someone reading this file a year from now, who never saw the diff? If it only makes sense beside the diff, it is changelog — delete it and put it in the commit body.

- *CC-3 (MUST)* Default to zero comments. Declarative config — Terraform, DNS records, k8s manifests, CI YAML, Helm values — is self-describing and takes none. A resource named `dmarc-example-com` does not need a comment saying it is the DMARC record.

- *CC-4 (MAY)* Comment only when a future editor would actively break something without it: a non-obvious external constraint, a required out-of-band manual step, an invariant the surrounding code cannot show. One line. If it needs a paragraph it belongs in `plans/`, not inline.

- *CC-5 (MUST)* Before every commit, re-read the comment lines I added: `git diff --cached | grep '^+' | grep -E '#|//|/*'`. Each hit must pass CC-2 on its own. Deleting is always an acceptable outcome. "I already wrote it", "it is only one line", and "this one is genuinely useful" are not exemptions — the last one is the exact thought that precedes every violation.

- *CC-6 (MUST)* Applies to comments I edit as well as ones I add. When a change invalidates an existing comment, the default action is DELETE, not rewrite it into a new narrative.

```

Yes, I am aware that claude mostly generated this, and it can probably be better and/or more succinct.

I think people really need to focus more on working with limited contexts rather than trying to work around it. I really try to keep my sessions as short as possible and it helps a ton with keeping Claude (et al) focused.

Specifically, I like the "canary" trick that people have discussed where you add a small, innocuous rule to your CLAUDE.md like "When responding to me, start every sentence with my name." so that when Claude stops doing this, you know you've used way too much context and need to start a new session.

Yea, I've started making it write linters to check the code that goes out. Anything that can be deterministically measured, gets added to it once we lock it down.

> The problem is, when the context window grows,

You know the problem; then why not address it? Does Compacting the context not help?

Hooks is the way.

Intermittent nudges