Context Vigilance

A framework for Human + AI collaboration: manage the context available to AI and collaborators with the same rigor you manage code. Every Lossless project has a context-v/ directory with (commonly) six subdirectories, organized into three cognitive modes: Prep, Reflective, and Journey.

Norms, not rules. Patterns here are loosely enforced. The team is generative-first; consistency emerges when attention focuses on a project, file, or pattern. Be generous reading existing files (they may pre-date current norms or be experiments) and careful writing new ones. See references/philosophy.md for the deeper rationale.

Drift policy: When you encounter inconsistencies (mismatched frontmatter, deviating filenames, partial-convention adoption), observe, note, surface, but do not auto-fix as a side effect of unrelated work. Cleanup happens only with explicit user permission. The user runs parallel agent sessions; silent normalization creates conflicts. (This rule lives globally in ~/.pi/agent/AGENTS.md; restated here for redundancy.)

Reference: <https://www.lossless.group/projects/gallery/context-vigilance>

When to use this skill

• The user asks you to create or edit any file under a context-v/ directory
• The user mentions specs, prompts, blueprints, reminders, explorations, or issues in the Lossless sense
• Starting a new project and setting up context-v/
• The user asks about context engineering, AI co-development, or "the context-v thing"

The Six Directories

Prep Mode (paired: spec ↔ prompt)

The work of deciding what to build is the work — "prep" here is not "minor pre-work", it's the deliberate forward construction phase. Specs and prompts are the artifacts.

• `context-v/specs/` — Living specifications. What you're building and why. Constantly updated. Single source of truth. Every prompt references a spec.
• `context-v/prompts/` — Step-by-step, prompt-by-prompt implementation documents (NOT single chat messages). Each prompt references specs/blueprints/reminders. Success at each step is verifiable before moving on.

A prompt without a spec is a vibe. A prompt within a spec is engineering.

Reflective Mode (paired: blueprint ↔ reminder)

• `context-v/blueprints/` — Codified patterns, architecture decisions, proprietary thinking. Institutional knowledge AI needs to respect the system (e.g., "how our extended markdown flavor works", component organization, naming rationale).
• `context-v/reminders/` — Short, sharp corrections born from repeated AI mistakes (e.g., "We don't use React. Astro + Svelte for interactivity. Do not hard-validate frontmatter."). Battle scars turned into guardrails.

Journey Mode (unpaired)

• `context-v/explorations/` — Documents where the destination is unclear. Research, prototype tradeoffs, option-space mapping, thinking out loud with AI as partner. Ends when you've learned enough to write a spec — or decided you don't need one.
• `context-v/issues/` — Issue-resolution journey logs. The painful, winding path through debugging. Capture so no human or AI has to retrace it.

When you find a seventh folder

The six are convention, not a closed set. Experimentation is normal — you'll encounter folders that don't match the six (e.g., notes/, decisions/, changelog/, plans/, research/). When that happens:

1. Don't fight it. Read what's there.
2. Identify the cognitive mode (planning / reflection / journey / something new).
3. Discuss with the user whether the folder should be assimilated (promoted to a new convention), folded (contents moved into one of the six), or kept as project-specific.
4. Default to keeping it if unsure. Re-organizing someone's mental model mid-session is rude.

Conventional Frontmatter

Frontmatter in context-v/ is scattered in practice — some files have lots of properties, some have very few. When creating new files, lead with this baseline:

---
title: "Human-readable title"
date_created: YYYY-MM-DD
date_modified: YYYY-MM-DD
authors:
  - Author Name
semantic_version: 0.0.0.1
tags:
  - Relevant-Tag
  - Another-Tag
---

When editing existing files, respect what's there. Don't add fields the file didn't have unless they're genuinely useful. Don't remove fields you don't recognize.

Key conventions (full details in references/frontmatter-spec.md):

• All property names are `snake_case` — enforced by Obsidian's frontmatter rendering. Never camelCase or kebab-case keys.
• Update date_modified whenever you edit the file
• semantic_version is four-part `epoch.major.minor.patch` — see references/versioning.md
• authors is humans only, always a list. AI agents are tracked separately under augmented_with (format: Pi on Claude Sonnet 4.5). See references/frontmatter-spec.md.
• tags use Train-Case values (e.g., Markdown-Rendering, Issue-Resolution) — Obsidian convention
• status uses Train-Case values too — it's a display string, not a machine enum
• lede (or description) is optional on any doc-type — a one-sentence newsroom hook for preview cards / OG snippets / list views

Status discipline

The status: field is the load-bearing signal of where a document sits in its lifecycle. A directory full of status: Draft plans, half of which actually shipped, is a directory you can't trust. Status reflects reality — promote it as work lands.

Canonical values (Train-Case display strings, not machine enums):

Draft → In-Review → Signed-Off → Implementing → Shipped · Partially-Shipped · Deferred · Stale · Superseded · Archived

Companion fields that must move with status:

• `Shipped` — set date_first_published: YYYY-MM-DD; optionally post_ship_note: for things learned after ship.
• `Partially-Shipped` — set date_first_published: for the first shipped slice; append a ## Remaining work (as of YYYY-MM-DD) section enumerating what's done and what's left.
• `Deferred` — set deferral_note: explaining the named reason.
• `Superseded` — set superseded_by: [[Successor-Doc]].

In every case, bump date_last_updated (or date_modified) on the same edit. Status changes are meaningful edits.

When to update: when you ship a substantial portion, defer explicitly, supersede, or notice the field doesn't match reality during a sweep.

When NOT to update: mid-session as a side effect of unrelated work (drift policy — surface, don't silently normalize); for docs authored by someone else whose ship state you're not sure about (ask first); as a way to "tidy up" without a real ship event to point at.

Full reference: references/status-discipline.md. The periodic sweep procedure: lossless-monorepo/context-v/habits/Maintain-Status-Discipline-Across-Context-V-Files.md.

Cross-references

Cross-referencing is how humans and agents focus on a limited scope at any moment — humans have context windows too. Three styles, all valid:

1. Obsidian-style backlinks (preferred): [[path/to/Filename.md]] or [[Filename]]
2. Standard Markdown links: [link text](../specs/Some-Spec.md)
3. Backtick paths: ` context-v/specs/Some-Spec.md ` for references the reader isn't expected to click

Use whichever serves the reader. Backlinks are preferred because most context-v/ directories are symlinked into Obsidian vaults, where [[wikilinks]] unlock graph view, autocomplete, and backlink panes.

Common linking patterns:

• prompts → link the spec they implement
• reminders → link the blueprint that explains the pattern
• explorations & issues → link whatever they relate to

Audience: User + Agent + Reader

Almost everything in context-v/ is destined for public web publishing through one of the Lossless Astro Knots sites. So every document balances three audiences:

1. The User writing or editing it
2. The Agent that will load it as context in some future session
3. The Reader who lands on it on the web with no prior context

Practical implications:

• Lead with marketing. Lead with why. Lead with something anyone can understand. Get into technical detail deeper in the doc.
• The first paragraph should be readable by an outsider. The rest can be specialized.
• Fork early; don't wait for "too long." Long-context-window models (Opus 4.7 with 1M tokens, etc.) can technically ingest huge documents — but creativity, cross-referencing, and human-agent cooperation all degrade as a single doc grows, regardless of what the model can accept. The trigger to split is anxiety about length, not a word count: when you (or the user) notice you're scrolling past sections to reach the one that matters, that's the cue. The practice is fork-and-cross-reference, not "split when forced." Pre-emptively factor self-contained sub-systems into sibling specs, reusable patterns into blueprints, and specific debugging journeys into issues — each linked from the parent. The parent doc keeps the map; the children carry the detail. See references/philosophy.md for the longer rationale.
• Common split shapes when forking: marketing/why stays at the top (or its own short doc), pattern/architecture → blueprint, thing-being-built → spec, how-to-build-it → prompt. Whatever fits.

Filename conventions

Use Train-Case for filenames: Train-Case.md. Same convention as tags. Matches existing examples like When-Claud-Code-and-When-Pi.md, Migrating-Study-to-its-own-Pseudomonrepo.md.

Decision tree: which folder?

• Defining what to build, with criteria & scope? → specs/
• Step-by-step implementation plan referencing a spec? → prompts/
• Capturing how/why a system is designed (pattern, architecture)? → blueprints/
• Short correction the AI keeps needing? → reminders/
• Don't know the answer yet, need to research/weigh options? → explorations/
• Debugging a specific painful problem and capturing the path? → issues/

When in doubt, see references/doc-type-guide.md.

Templates

When creating a new file, start from the matching template in templates/:

• templates/spec.md
• templates/prompt.md
• templates/blueprint.md
• templates/reminder.md
• templates/exploration.md
• templates/issue.md

Typical flow for a context-v/ task

Not a checklist — a default rhythm. Adjust to the situation.

1. Locate the project's `context-v/`. Walk up from cwd if needed. Some repos have multiple (e.g., one per sub-project).
2. Survey what's there. Look at sibling files for tone, depth, and frontmatter conventions. Match them.
3. Pick the folder using the decision tree. If nothing fits, see When you find a seventh folder above.
4. Copy the matching template from templates/ if helpful, or write from scratch matching nearby files.
5. Frontmatter: today's date for both date_created and date_modified. Start at 0.0.0.1. Add the user as author. If you (an AI) contributed materially, add yourself under augmented_with (e.g., Pi on Claude Sonnet 4.5) — not under authors.
6. Lead with the why. First paragraph readable by an outsider.
7. Cross-link to related docs using [[wikilinks]].
8. Filename & tags: Train-Case (My-New-Doc.md, tags like - New-Pattern).
9. When editing an existing doc: bump semantic_version per references/versioning.md and update date_modified. Respect existing frontmatter shape.
10. If the doc is ballooning, propose a split before continuing. Better two clean docs than one bloated one.

Developing a spec (the rich case)

Specs have more rhythm than the other doc-types: stub-first, discuss-then-write, handle stale prior art without hijacking the primary dialog, sign-off gate before implementation, narrative pass after sign-off, and pair with prompts for chunked execution. The full rhythm lives in references/developing-a-spec.md — load it whenever you're initiating or developing a spec with the user.

The philosophy (tl;dr)

• AI doesn't learn between sessions → externalize memory as loadable docs
• Context windows have limits (humans too) → modular docs designed for selective loading and cross-linking
• Specs align everyone again, better → AI makes specs cheap to write and cheaper to keep current
• We publish in public → docs serve users, agents, and outside readers simultaneously
• Norms over rules → generative first, consistency emerges with attention

For the deeper version, see references/philosophy.md.