Progressive Disclosure for Long Chat Replies

Attach long replies as files; show only the summary in chat.

Tone & Voice

Operational convention. applies AUTOMATICALLY without a user prompt. The chat summary should be terse, 3 lines max, with an explicit "full content in attached file" pointer. Hard rule: when triggered, do NOT ask "should I attach?". just attach. Asking defeats the friction-reduction purpose.

Procedure (thinking step by step)

1. Compose the full reply mentally.
2. Count chars (excluding markdown table chars). If >1500 → trigger. Count table rows. If 8+ → trigger.
3. Save full content to outputs/tg/reply-<ISO>-<slug>.md (auto-generated path).
4. Generate a 3-line summary: (a) topline result, (b) key tradeoff or finding, (c) "see attached for full details".
5. Reply via the chat reply tool with the summary text + files: ["<path>"] attached.

Rule (apply automatically, no user invocation needed)

Trigger any of:

• Reply text exceeds 1,500 characters (excluding markdown table chars)
• Markdown table has 8+ data rows
• Code block exceeds 30 lines
• Total markdown structure has 5+ headed sections

When triggered:

1. Write the full reply content to outputs/tg/reply-YYYY-MM-DDTHH-MM-SSZ-{slug}.md with frontmatter (date, type=chat-reply, related-thread-context)
2. Send via the reply tool with:
   • text = 3-line summary describing what's in the file + the headline takeaway
   • files = [<absolute path to the .md>] so it attaches as a doc
3. The summary text MUST include: (a) what the file contains, (b) the 1-line headline / decision / rec, (c) any explicit ask of the user

When NOT to trigger:

• Tables under 8 rows or under 1,500 char total
• User explicitly says "give me the full thing inline" / "paste it here"
• Code snippets with under 30 lines
• Quick lookups, status updates, single-decision answers
• Replies that are inherently a wall (e.g. JSON dumps for verification): those go in the file regardless of length

Why this rule exists

Long replies in a mobile chat are friction:

• Mobile-readable only by scrolling endlessly
• Chat message format hides nested structure (markdown tables get cramped)
• Every long reply re-renders into the conversation transcript = future-session token cost
• File attachments are first-class on mobile (open in a markdown viewer or files app)

Saving the wall as a .md attachment is archival-ready (you can drop it in outputs/reviewed/ if it's worth keeping) and mobile-friendly (one tap to open, native scroll, formatting preserved).

Example application

User asks for a "component pattern library scan". The reply would be 800+ lines, 4 sections, tables.

❌ Old behavior: paste the entire library in the chat message, mobile reading nightmare. ✅ New behavior:

1. Save the library to outputs/drafts/component-pattern-library-2026-04-24.md
2. Reply: "📎 Component pattern library shipped. component-pattern-library-2026-04-24.md attached. 10 patterns / 4 domains, 47% low-complexity can deploy within 90 days. Quick-match index at the bottom."
3. files = ["/abs/path/component-pattern-library-2026-04-24.md"]

Source-of-truth

This rule supersedes the implicit "should I attach or paste" judgment call. Apply consistently. If unsure, attach. bias toward file delivery for anything that isn't trivially short.

Edge cases

• CONFIRM-gate /scope responses: those are short by design (restate + assumptions + NOT-doing + ask). Stay in chat.
• Multi-step plans: if the plan needs your pick from N options, paste in chat (you need to see options + reply quickly). Save the EXPANDED rationale to a file if it would push the chat reply over 1,500 chars.
• File contents you asked to read: if you paste a doc and ask for a review, reply summary in chat + attach annotated diff or review notes as .md.
• Cover letter / resume / proposal drafts: ALWAYS attach as a file. these get edited iteratively, file is the canonical artifact.

Implementation notes (for the default persona)

• outputs/tg/ directory exists; create if missing on first use
• File naming: ISO timestamp + 3-5 word kebab-case slug (e.g. reply-2026-04-25T10-15-00Z-audit-summary.md)
• Summary line format: 📎 {filename}.md. {1-line takeaway}. (3 lines max if context calls for more)