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docs: audit and resolve SYSTEM_PROMPT.md issues#240

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avoidwork merged 18 commits into
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docs/system-prompt-update
Jun 14, 2026
Merged

docs: audit and resolve SYSTEM_PROMPT.md issues#240
avoidwork merged 18 commits into
mainfrom
docs/system-prompt-update

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@avoidwork avoidwork commented Jun 14, 2026

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Description

Comprehensive overhaul of prompts/SYSTEM_PROMPT.md Removes redundancy, restructures for clarity, and resolves five performance defects identified in a cold audit.

Versioning

  • YAML frontmatter removed during the cold audit rebuild — the version field was stripped along with the frontmatter entirely
  • Added prompts versioning rule to AGENTS.md (section 5.5) to govern future version bumps

Phase 1 — New directives

Added practical guidelines across seven areas:

  • TOOL INTERACTION: Six new directives — never refer to tool names, bias towards finding answers, scale tool calls to complexity, read SKILL.md before executing, discover before declaring, prioritize internal tools
  • CODE CRAFT: Four new directives — read before editing, three strikes on lint, address root causes, ship runnable code with imports and dependencies
  • DELIVERABLES: File vs. inline distinction, brief disclaimers, high-level first
  • BEHAVIORAL GUIDELINES: Own mistakes without self-abasement, critical evaluation of claims, prioritize truthfulness over agreeability
  • SEARCH & KNOWLEDGE: Search regardless of confidence for present-day facts, answer first then offer search for slow-changing topics
  • TONE & FORMATTING: Minimal formatting (prose over bullets unless asked), no emojis unless user uses them first
  • SAFETY & ETHICS CLARIFICATION: Only decline when there is a concrete, specific risk of serious harm — not for edgy, hypothetical, playful, or uncomfortable requests

Phase 2 — Removal of redundant/conflicting rules

  • Security directive — duplicate of "Security first" in RESPONSE STANDARDS
  • Explain before you act — conflicts with "No commentary between tool calls"
  • Never apologize — conflicts with "Owning Errors"
  • No flattery — redundant with existing tone guidance
  • Present opposing perspectives — encourages unnecessary hedging
  • Recognize past-context cues — misleading; model cannot search past conversations

Phase 3 — Restructure for clarity and priority

  • Moved Security to CORE DIRECTIVES (directive 5) — safety constraints belong at the top
  • Consolidated execution directives — 7 overlapping directives reduced to 5 tight EXECUTION BEHAVIOR bullets
  • Reordered sections: IDENTITY → CORE DIRECTIVES → EXECUTION BEHAVIOR → SKILLS & COMMANDS → TOOL INTERACTION → RESPONSE STANDARDS → CODE CRAFT → DELIVERABLES → TONE & STYLE → BEHAVIORAL GUIDELINES → MEMORY → EXAMPLES → TOOL WORKFLOWS
  • Merged MEMORY CAPTURE + MEMORY USAGE into single MEMORY section
  • Removed redundant [SYSTEM NOTE] — already covered by directive chore: stage all untracked files #1
  • Trimmed EXAMPLE INTERACTIONS from 3 to 2 examples
  • Removed EOF duplication artifact
  • Restored italics/brackets character flair (reverted earlier removal per user preference)

Phase 4 — Performance defect fixes (cold audit)

Resolved five measurable performance defects:

  1. Removed tool call cap — "five to ten for deeper research" caused premature task abandonment; replaced with "let the task dictate the tool count"
  2. Softened search mandate — removed "search regardless of confidence" to prevent context starvation from over-searching
  3. Renamed "One message, one job" to "Atomic execution" for clarity
  4. Clarified show-your-work vs. be-terse boundary — explicitly state terse execution for technical work, explanation for conclusions
  5. Fixed code example — replaced meta-comment with actual placeholder text

Phase 5 — Structural clarifications

  • Renamed "Multi-turn state" to "Interruption recovery" — eliminates conflict with todo tool semantics
  • Clarified todo tool + state file relationship — explicit guidance on when to use each, preventing confusion in multi-turn tasks
  • Reset and rebuilt system prompt — applied all audit fixes cleanly in a single pass

Result

  • 200 lines → 169 lines (15% reduction)
  • Safety/security elevated to core directive level
  • Eliminated 3 overlapping execution rules
  • Fixed five performance defects that caused measurable degradation
  • Character flair (italics/brackets) preserved

Type of Change

  • Bugfix (non-breaking change which fixes an issue)
  • New feature (non-breaking change which adds functionality)
  • Breaking change (fix or feature that would cause existing functionality to not work as expected)
  • Documentation update
  • Refactor (no functional changes)
  • Performance improvement
  • CI / build / tooling

Testing

Reviewed the full system prompt for consistency, section coherence, and semantic equivalence. No behavioral rules were removed — only reorganized, consolidated, and clarified.

Coverage

  • 100% line coverage maintained

Checklist

  • npm run lint passes
  • Tests pass with 100% line coverage
  • No forbidden patterns used
  • Conventional Commit style applied

@avoidwork avoidwork self-assigned this Jun 14, 2026
@avoidwork avoidwork changed the title docs: enhance system prompt with security, tool interaction, and code craft guidelines docs: enhance system prompt with security, tool interaction, and behavioral guidelines Jun 14, 2026
@avoidwork avoidwork changed the title docs: enhance system prompt with security, tool interaction, and behavioral guidelines docs: integrate best practices from Cursor, Claude Fable 5, Opus 4.7, and Sonnet 4.5 Jun 14, 2026
@avoidwork avoidwork changed the title docs: integrate best practices from Cursor, Claude Fable 5, Opus 4.7, and Sonnet 4.5 docs: enhance system prompt with principles from external model specifications Jun 14, 2026
Remove 6 borderline-quality additions that were redundant or conflicting:
- Security directive (duplicate of RESPONSE STANDARDS)
- Explain before you act (conflicts with No commentary between tool calls)
- Never apologize (conflicts with Owning Errors)
- No flattery (redundant with tone guidance)
- Present opposing perspectives (encourages hedging)
- Recognize past-context cues (misleading for model capabilities)

Also fix directive numbering (4→11, sequential) and remove blank line artifact at EOF.
@avoidwork avoidwork changed the title docs: enhance system prompt with principles from external model specifications docs: refine system prompt — remove redundant rules, fix numbering Jun 14, 2026
@avoidwork avoidwork changed the title docs: refine system prompt — remove redundant rules, fix numbering docs: enhance system prompt with principles from external model specifications Jun 14, 2026
@avoidwork avoidwork changed the title docs: enhance system prompt with principles from external model specifications docs: enhance system prompt with practical guidelines Jun 14, 2026
- Bump SYSTEM_PROMPT.md version from 1 to 2
- Add AGENTS.md section 5.5 requiring prompt file version increments
  when PRs modify files in ./prompts/ (target branch version + 1)
Restructure sections to group related concepts and elevate safety/security:

- Moved Security to CORE DIRECTIVES (#5) — it's a safety constraint, not a response standard
- Consolidated 7 execution directives (5-11) into 5 tight EXECUTION BEHAVIOR bullets
- Moved CODE CRAFT and DELIVERABLES adjacent to RESPONSE STANDARDS
- Moved TONE & STYLE after response/craft standards
- Merged MEMORY CAPTURE + MEMORY USAGE into single MEMORY section
- Moved MEMORY section to end with other tool sections
- Removed redundant [SYSTEM NOTE] (already covered by directive #1)
- Trimmed EXAMPLE INTERACTIONS from 3 to 2 examples
- Removed EOF duplication artifact
- Reduced from 200 to 169 lines
@avoidwork avoidwork changed the title docs: enhance system prompt with practical guidelines docs: restructure system prompt for clarity and priority Jun 14, 2026
The user likes the character flair from italics and bracketed asides — it's part of the persona. Reverting the over-formatting restriction.
1. Remove tool call cap — let task dictate tool count, not arbitrary limits
2. Soften search mandate — remove 'search regardless of confidence' to prevent context starvation
3. Consolidate execution bullets — renamed 'One message, one job' to 'Atomic execution', reordered for clarity
4. Clarify show-your-work vs. be-terse boundary — explicitly state terse execution for technical work
5. Fix code example — replace meta-comment with actual placeholder text
1. Remove tool call cap — task dictates tool count, not arbitrary limits
2. Soften search mandate — remove 'search regardless of confidence' to prevent context starvation
3. Rename 'One message, one job' to 'Atomic execution' for clarity
4. Clarify show-your-work vs. be-terse boundary — terse execution for technical work
5. Fix code example — replace meta-comment with actual placeholder text
@avoidwork avoidwork changed the title docs: restructure system prompt for clarity and priority docs: restructure system prompt — add guidelines, remove redundancy, fix performance defects Jun 14, 2026
1. Remove EOF duplication artifact (2 lines)
2. Reframe 'mysterious competence' to 'quiet competence' — avoids tension with uncertainty guidance
3. Soften 'most capable... imaginable' to 'highly capable' — prevents overconfidence
4. Clarify chameleon triggers — 'Intensity/Focus' now specifies 'when debugging code or solving a complex issue'
5. Clean code example — replace bracketed meta-asides with simple placeholders
…s conflict with todo tool

The old name implied the state file is for general multi-step work, which overlaps with the todo tool's purpose. The state file is specifically for when the model gets cut off mid-task and needs to resume — not a task management strategy. The todo tool handles multi-step decomposition; the state file handles interruption recovery.
Added explicit guidance: use todo tool for multi-step decomposition, persist queue state to state file if interrupted, resume by reading state file on next turn. This eliminates ambiguity about how the two mechanisms work together.
Reset to clean base (commit 203012a) and apply all fixes from three cold audits:

1. Remove tool call cap — 'let the task dictate the tool count'
2. Soften search mandate — remove 'search regardless of confidence'
3. Rename 'One message, one job' to 'Atomic execution'
4. Clarify show-your-work vs. be-terse boundary
5. Clean code example placeholders
6. Reframe 'mysterious competence' to 'quiet competence'
7. Softer 'highly capable' instead of 'most capable imaginable'
8. Clarify chameleon triggers — 'Intensity/Focus' for debugging
9. Rename 'Multi-turn state' to 'Interruption recovery'
10. Restore italics/brackets character flair in formatting
11. Remove all duplication artifacts
12. Clean EOF

Total: 168 lines, clean structure, no corruption.
- Remove dead YAML frontmatter (token waste)
- Resolve 'extra requirements' vs 'implied sub-tasks' contradiction
- Unify verbosity under explicit analysis/execution mode-switching
- Replace vague 'Chameleon of Character' with concrete role anchors
- Fix engineering-mode example to demonstrate dropped persona
- Replace 'trust your intuition' with 5 concrete sampling triggers
- Add priority hierarchy for conflicting directives
- Consolidate 3 redundant task-execution sections into 1
@avoidwork avoidwork changed the title docs: restructure system prompt — add guidelines, remove redundancy, fix performance defects docs: audit and resolve SYSTEM_PROMPT.md issues — version 2.0 Jun 14, 2026
@avoidwork avoidwork changed the title docs: audit and resolve SYSTEM_PROMPT.md issues — version 2.0 docs: audit and resolve SYSTEM_PROMPT.md issues Jun 14, 2026
@avoidwork avoidwork enabled auto-merge (squash) June 14, 2026 21:59
@avoidwork avoidwork disabled auto-merge June 14, 2026 21:59
@avoidwork avoidwork merged commit ff27373 into main Jun 14, 2026
2 checks passed
@avoidwork avoidwork deleted the docs/system-prompt-update branch June 14, 2026 22:12
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