Changelog Conventions

Changelog Conventions

The single most important rule: it exists. Everything else is refinement.

Every Lossless repo at every level (project, true monorepo, pseudomonorepo) should have a changelog/ directory at the root, parallel to context-v/. Entries are written when meaningful chunks of work ship — or at least when they push.

Changelog First Development is a working Lossless theory: a fast-moving, meaningful changelog signals momentum to clients, audiences, contributors, and your own future self. The bus is leaving. The cruise ship is full. See references/changelog-first-development.md.

When to use this skill

• You just shipped or pushed a coherent chunk of work
• The user says "log this", "write a changelog", "ship note", "publish update"
• Scaffolding a new repo's changelog/ directory
• Reviewing or updating an existing changelog entry
• Authoring a product release message (see releases/ subfolder below)

When to write an entry

Yes:

• A coherent chunk of work shipped (deployed, merged, released)
• Or at least pushed to a remote where someone else might land on it
• A new convention, blueprint, or tool became available
• Multiple smaller changes have accumulated into something worth announcing

Not necessarily:

• Every commit (most aren't worth a changelog)
• Typo fixes, minor refactors, work-in-progress

Future direction: the team is open to a "tweet-style" subset — short, frequent micro-changelogs for the in-between work that doesn't merit a full entry. Not implemented yet; flagged as a candidate.

Where it lives

<any-repo>/
├── context-v/        # living documentation
└── changelog/        # ← this skill governs this directory
    ├── YYYY-MM-DD_NN.md       # entries
    ├── YYYY-MM-DD_NN.md
    └── releases/              # for product-style projects only
        ├── v1.0.0.md
        └── v1.1.0.md

• Filename: YYYY-MM-DD_NN.md where NN is a daily counter (01, 02, ...). ISO date with dashes — always.
• releases/ subfolder: only for product-style projects with versioned releases. Release messages live there as <version>.md (or whatever versioning scheme the product uses). Standard changelog entries live in changelog/ proper.

Mandatory frontmatter (last few months and forward)

These six fields are hardcoded for new entries — non-negotiable. Older entries may have less or more; respect them.

---
date_created: YYYY-MM-DD       # ISO with dashes. Set on creation.
date_modified: YYYY-MM-DD      # ISO. Updated on every edit. Obsidian template often manages this; sometimes meaningless updates happen, that's accepted.
title: "Human-readable title"
lede: "Subtitle that grabs attention — used where the point is to make the reader keep reading"
publish: true                  # Obsidian publisher convention. STRICTLY ENFORCED. Do not deviate.
authors:                       # Humans only. Always a list. Preferred ul format (not [a, b] inline).
  - Firstname Lastname
augmented_with:                # AI tools used. Format: "<tool> on <model name version>".
  - Pi on Claude Sonnet 4.5
files_changed:                 # Optional but strongly recommended. Paths from project root.
  - src/components/NameOfComponent.astro
  - context-v/blueprints/Some-Blueprint.md
---

Notes on the fields

• publish: true is set by Obsidian publisher and is strictly enforced there. Do not toggle it off without understanding the publishing implications.
• lede is intentional — not "subtitle" or "description". The word signals: write something that grabs attention. The reader should want to keep reading.
• authors is for humans only. Preferred form is the YAML list (one author per line), not inline [a, b]. AI agents do not go here, even when they wrote substantial content.
• augmented_with is for the AI tooling that helped produce the entry. Format is <tool> on <model name version>, e.g., Pi on Claude Sonnet 4.5, Claude Code on Claude Opus 4, Cursor on GPT-5. Same ul-list preference as authors. Include this field whenever an AI agent contributed materially — honesty about augmentation matters more than authorship credit.
• ISO dates with dashes for everything — both dates and timestamps. Never 2026/05/04 or May 4, 2026.

See references/frontmatter-spec.md for edge cases and optional fields.

Public by default

Changelogs are written for the public web. Assume:

• A reader with no prior context lands on this entry from a Google search
• The lede has to do its job in two seconds
• Internal jargon needs a one-sentence translation or a [[wikilink]]
• Embarrassments and bugs can be discussed honestly — that's part of building in public

A long-running goal: aggregate all changelogs across all Lossless repos via the GitHub API into a "Lossless Changelog" umbrella view. Write entries that would render well in that aggregated context.

Show, don't enforce

Conventions here are evolving. People are encouraged to experiment. The way to spread the convention is to show it working — not to police existing entries.

• ✅ Write your own entries to the convention
• ✅ Nudge a contributor toward the format when they ask
• ❌ Go around "fixing" old entries to match current frontmatter
• ❌ Reject a PR for using description instead of lede

The aspiration is consistency. The reality is generative-first. Respect that.

Reference / submodule projects

Don't expect them to have proper changelogs or frontmatter. Many submodules in our pseudomonorepos are external projects we're studying or vendoring. They are out of scope for our conventions. When working on an external project's content, follow that project's conventions; when working in our code, follow these.

Body shape: lead with the previewable sections

List views and preview cards on the rendered site use the first body sections as previews — just like the lede. Structure entries so the first two sections after the title can stand alone:

1. ## Why Care? — the audience-facing answer. Why does this matter to a reader who isn't on the team? One to three short paragraphs.
2. ## What's New? — the concrete summary. Bullet list or short paragraphs of the actual changes, links to artifacts.
3. (Then go deeper.) — the how, the journey, the visuals, the technical details. Readers who care will follow you down. Readers who don't have already gotten the value.

Unless the audience is contributors specifically, lead with Why Care? not with What's New?. The audience cares about impact before inventory.

Both headings are phrased as questions — the parallel rhetorical shape ("Why Care? What's New?") signals to the reader that the entry is having a conversation with them, not lecturing them.

Length: not a factor

Rendering a Markdown file through an SSG costs nothing. Write what's needed — no more, no less. Don't pad to look thorough; don't trim to look tight.

The failure modes seen in practice:

• "Make it concise" → too concise, loses the journey
• "Make it robust" → padded with irrelevant minor nonsense

The target: enough to convince someone to care, plus enough that a reader who cares can follow along and learn something meaningful.

Tell a story

A changelog entry is a small journey, not a journal entry and not a list of disconnected fixes.

• ✅ A coherent arc: "We hit X, tried Y, learned Z, here's what shipped"
• ✅ The struggle plus the resolution — readers learn from both
• ❌ Two paragraphs of miscellaneous CSS fixes — not a story
• ❌ A yak-shaving rabbit hole with no resolution — not a story by itself

If you can't articulate the arc, the work probably isn't ready for a changelog entry yet. Combine with related work, or wait.

Voice

We are moving fast and learning a ton and we are excited to share this with you. We speak human, we are human. But we are nerdy and we open our nerdy doors.

In practice:

• First person plural ("we shipped", "we tried") for team work; first person singular when accurate
• Active verbs, present tense for what's now true, past tense for the journey
• Direct address to the reader is welcome
• Jokes that land are welcome; jokes that don't land are skipped
• Show your work — don't hide the messy middle
• Don't use corporate filler ("various improvements", "enhanced experiences")

See references/voice-and-shape.md for the full voice/shape guide with examples.

Use visuals

Visuals make entries skimmable, memorable, and honest about complexity. Use them generously:

• Code blocks in fences — with language tags for syntax highlighting
• Mermaid diagrams — flowcharts, sequence diagrams, state diagrams
• ASCII diagrams — for tree structures, simple boxes-and-arrows, rendering everywhere
• Tables — when comparing options or showing before/after
• Screenshots — for UI work, embedded as relative-path images

The rule: pretend you need to convince someone to care, and pretend anyone who cares wants to follow along and learn something meaningful. Show enough of the "how we did this" that it clicks for the reader who reads that far.

Templates

When creating a new entry, start from templates/entry.md (standard changelog) or templates/release.md (product release).

Composition with other skills

• pseudomonorepos — the lossless-loop Phase 2 (Progress) and Phase 4 (Publish) both write to changelogs. Project changelog = Progress. Parent pseudomonorepo changelog = Publish.
• context-vigilance — changelogs sit alongside context-v/, not inside it (aspirationally). Some legacy projects nest them; respect what's there.
• astro-knots — changelog content gets aggregated and rendered on Astro Knots sites. Write with that publication path in mind.

Typical flow

1. You just shipped something. Pause before opening a new task.
2. Decide: is this a coherent chunk worth logging? (Apply the "Yes/Not necessarily" guide above.)
3. Find the changelog/ at the repo root. Create it if missing.
4. Filename: YYYY-MM-DD_NN.md. Increment NN if today already has entries.
5. Copy templates/entry.md. Fill in frontmatter (all 6 fields, ISO dates, publish: true).
6. Write the lede first. If you can't write a compelling lede, the work might not warrant an entry.
7. Body: what shipped, why it matters, what it enables next. Link related work via [[wikilinks]].
8. Commit and push. This entry is part of the work, not separate from it.

See also

• references/frontmatter-spec.md — full frontmatter rules, optional fields
• references/filename-conventions.md — daily counter, releases subfolder
• references/what-counts.md — heuristics for when an entry is warranted
• templates/entry.md, templates/release.md — scaffolds
• pseudomonorepos/references/lifecycle-workflow.md — how changelogs fit the 5-phase loop