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Status:✏️ DRAFT
Date:📅 unknown
Domain:📦 Retroactive Issue Management

Design: Retroactive Issue Management

Context​

📝 ADR-0009 decided to add project grouping and developer workflow conventions (branch naming, PR close keywords) to the /sdd:plan skill, with opt-out flags. It also decided to create two separate retroactive skills -- /sdd:organize and /sdd:enrich -- for applying these conventions to issues that already exist. SPEC-0007 covers the forward-looking additions to /sdd:plan; this spec (SPEC-0008) covers the retroactive skills exclusively. See 📝 ADR-0009 and SPEC-0007.

Goals / Non-Goals​

Goals​

  • Enable retroactive project grouping for issues created by prior /sdd:plan runs
  • Enable retroactive branch naming and PR convention enrichment for existing issue bodies
  • Share spec resolution and tracker detection logic with /sdd:plan for consistency
  • Support dry-run previews so users can verify changes before applying them
  • Be idempotent: safe to run multiple times without duplicating projects or sections
  • Read .claude-plugin-design.json for saved preferences to minimize re-prompting

Non-Goals​

  • Re-creating issues (both skills operate on existing issues only)
  • Modifying acceptance criteria or issue content beyond appending ### Branch and ### PR Convention sections
  • Supporting --review mode (both are utility skills, not authoring skills)
  • Syncing issue state back to spec artifacts
  • Creating issues for requirements that lack corresponding tracker issues (use /sdd:plan instead)
  • Supporting trackerless environments (both skills require a live tracker connection)

Decisions​

Separate skills over combined skill​

Choice: Two separate skills (/sdd:organize and /sdd:enrich) rather than a single /sdd:workflow or a mode flag on /sdd:plan. Rationale: Organize and enrich operate on different tracker primitives. Organize creates projects and manages membership (no issue content changes). Enrich modifies issue bodies (no project operations). Their allowed-tools overlap but their concerns do not. A user may want to organize without enriching, or vice versa. Separate skills follow the plugin's single-purpose skill convention (see 📝 ADR-0003). Alternatives considered:

  • Combined /sdd:workflow skill with --organize and --enrich flags: Violates single-purpose convention; forces a large allowed-tools union; confusing invocation surface
  • Flags on /sdd:plan (--retroactive): Overloads planning with a fundamentally different operation (modifying existing issues vs. creating new ones)

Shared spec resolution and tracker detection​

Choice: Reuse the same spec resolution (SPEC number or capability name) and tracker detection (.claude-plugin-design.json → ToolSearch + CLI probing) flows from /sdd:plan. Rationale: Users already understand these patterns from /sdd:plan. Consistency reduces cognitive load and ensures .claude-plugin-design.json preferences work identically across all three skills. The duplication is in the SKILL.md instructions only -- there is no shared code to maintain. Alternatives considered:

  • Accept only SPEC numbers (not capability names): Inconsistent with /sdd:plan; users would have to look up the SPEC number
  • Skip .claude-plugin-design.json and always prompt: Adds friction; defeats the preference persistence from 📝 ADR-0008

Choice: Search for issues containing the spec number (e.g., "SPEC-0007") in their body text using the tracker's native search API. Rationale: Every issue created by /sdd:plan includes a spec reference in its body (per SPEC-0007, Requirement: Issue Creation Flow). Searching by spec number reliably discovers these issues. Tracker-native search is fast and requires no local state. Alternatives considered:

  • Maintain a local issue manifest in .claude-plugin-design.json: Adds complexity; goes stale when issues are deleted or moved
  • Search by label (e.g., spec:SPEC-0007): Not all trackers support structured labels; /sdd:plan does not currently set labels

Epic classification heuristics​

Choice: Classify issues as epics if their title starts with "Implement " or they have an epic label. Rationale: /sdd:plan creates epics with titles following the pattern "Implement {Capability Title}" (SPEC-0007). The epic label provides a fallback for manually created epics or tracker-specific labeling conventions. These heuristics are simple, deterministic, and match the existing planning output. Alternatives considered:

  • Require an explicit epic label: Too strict; /sdd:plan doesn't currently add labels
  • Use the tracker's native epic type (GitHub Projects item type, Jira epic issue type): Not all trackers distinguish epic types; adds tracker-specific branching to classification logic

Two-pass enrichment (read then update)​

Choice: For each issue, read the body first to check for existing sections, then update with appended content. Rationale: Idempotency requires checking whether ### Branch and ### PR Convention sections already exist. Blindly appending would create duplicates. The two-pass approach (read body, check for sections, append if missing, write) is the simplest way to achieve idempotency. Alternatives considered:

  • Track enriched issues in .claude-plugin-design.json: Adds local state that can go stale; the issue body is the source of truth
  • Use a marker comment instead of section headers: Less readable; section headers serve as useful documentation for developers

Architecture​

Risks / Trade-offs​

  • Tracker search accuracy: Searching issue bodies for "SPEC-XXXX" may return false positives if the spec number appears in unrelated contexts (e.g., comments referencing the spec). Mitigation: the spec number format is distinctive (SPEC- prefix with zero-padded digits); false positives are unlikely and harmless (the skill checks for epic/task classification before acting).
  • GitHub Projects V2 API complexity: GitHub Projects V2 uses a GraphQL-only API with separate concepts for projects, items, and fields. The gh project create and gh project item-add CLI commands abstract most of this, but edge cases (organization vs. user projects, project visibility) may require additional handling. Mitigation: use ToolSearch to discover MCP tools first; fall back to CLI; graceful failure on project creation errors.
  • Rate limiting during enrichment: Enriching many issues involves one read and one write API call per issue. For large specs with 20+ tasks, this could hit rate limits. Mitigation: the skill processes issues sequentially; individual failures are reported and skipped without blocking the rest.
  • Issue body format assumptions: The enrichment skill assumes issue bodies are markdown and that appending ### Branch sections at the end is appropriate. If trackers use different body formats (e.g., Jira's wiki markup), the appended content may not render correctly. Mitigation: the ### Branch and ### PR Convention sections use simple markdown that renders acceptably in most contexts.
  • Stale .claude-plugin-design.json project IDs: If a project is deleted from the tracker but its ID remains cached in .claude-plugin-design.json, the organize skill will attempt to reuse it and fail. Mitigation: the skill handles project-not-found errors gracefully and falls back to creating a new project.
  • Epic classification heuristics may miss custom epics: The "Implement " title prefix and epic label heuristics may not catch epics created with different naming conventions. Mitigation: these heuristics match /sdd:plan's output; manually created epics would need to follow the convention or be labeled.

Open Questions​

  • Should /sdd:organize support linking tasks to epics within a project (e.g., GitHub Projects V2 parent-child relationships) or just add all items flat?
  • Should /sdd:enrich offer to create the branch in git (not just document it in the issue body)?
  • Should there be a combined /sdd:organize --enrich shorthand to run both in sequence?
  • When /sdd:plan creates issues with branch/PR sections (per SPEC-0007 updates), should /sdd:enrich detect and respect those as already-enriched?

Direct relationships declared in YAML frontmatter (per ADR-0023 / SPEC-0018). Run /sdd:graph chain SPEC-0008 for the transitive view.