Roadmap: Post-compression Finder toolkit, automation, and release quality #1

Latest implementation checkpoint (2026-10-17)

Three independently reviewed and macOS-CI-verified PRs have been merged into main:

• #17 — transactional, source-identity-checked batch renames; streaming Copy As SHA-256; selection-relative paths; regression tests; current-feature README. Merge 4a1d6125.
• #18 — per-input batch errors, partially completed state, persisted failures, Activity details, successful-output tracking for verified Undo. Merge 9f4adb4b.
• #19 — metadata/checksum work moved off UI actor, streaming metadata hashes, partial/cancelled PDF split outputs retained and tested. Merge 9f41a2f7.

All three PR heads passed their respective macOS Swift 6 unit/toolkit/IPC tests and ad-hoc signed app/extension builds. These are implementation milestones, not proof that the entire roadmap is finished.

Open gates

• [Phase 2] Audit and finish PDF, image, metadata, and Finder utilities #2: remainder of advanced rename UI, comprehensive page reordering/preview, atypical documents/codecs and end-to-end review.
• [P0] Complete physical Finder and Settings validation for compression + helper IPC #3: user confirmed Settings UI/titlebar looks good on Mac; independent physical Finder right-click/output/Undo matrix remains outstanding.
• [Phase 3] Background operation center: queue, progress, cancellation, and retry #4/[Phase 3] Action history and safe undo for reversible Finder operations #5: stronger external-tool cancellation, interrupted-job recovery, additional Undo edge cases and manual Finder tests.
• [Quality] Scale Finder IPC and selections while keeping menus instant #13/[Quality] Native macOS polish, accessibility, and consistent interaction design #14/[Release] Documentation, regression gates, packaging, signing, and distribution readiness #15: large-selection/performance, accessibility/release packaging and optional dependency review.
• [Enhancement] Before/after preview for image and PDF compression #6–[Phase 4] Optional watched folders with explicit opt-in automation rules #12: optional enhancements remain not implemented.

Review these before closing issues; do not equate merged code with physical Finder sign-off.

Goal

Track the remaining work to turn Tuck into a fast, safe, native macOS Finder power-user utility without growing into a replacement for Finder, Raycast, or Hazel.

This is a planning issue, not a claim that any feature is already implemented. Review the local working tree and agent handoff reports before starting each issue: GitHub main may lag behind local, uncommitted development.

Product principles

• Select items in Finder → choose a relevant Tuck action → receive an output alongside the source, highlighted in Finder.
• Do not destructively modify original files by default. Require a preview/confirmation for renames, moves, deletes, or any potentially irreversible edit.
• Keep menus contextual, compact, keyboard accessible, and fast; expensive work runs asynchronously outside Finder.
• Maximize file fidelity under an exact user-selected size cap, never add "quality modes" to compression.
• Reuse Swift 6, AppKit/SwiftUI, authenticated Finder extension ↔ helper IPC, shared output-naming conventions, and existing compression test infrastructure.
• Respect external storage: verify mounted build/scratch paths; avoid silent fallback of large disposable artifacts to the internal SSD. Preserve source worktrees and unrelated files.
• Do not push, merge, release, or add AI attribution as part of implementation without explicit approval.

Workstreams

• Finish/verify Phase 2: PDF/image utilities, mixed PDF merging, OCR, metadata cleanup, Copy As, advanced rename and contextual menus.
• Phase 3: queued operations, progress/cancel/retry, action history, and safe undo.
• Phase 4: custom actions and Shortcuts, keyboard access, reusable recipes and optional folder watchers.
• Quality + release: visual comparisons, archive tools, duplicates, favorite destinations, Finder scalability, accessibility, packaging, and documentation.

Definition of done for a linked issue

• Isolated scope, regression tests and precise failure reporting.
• Original-file hashes unchanged for read/copy/transform operations; correct collision-safe output publishing.
• Swift 6 build and existing compression/IPС test suite pass.
• Physical Finder verification when feasible; otherwise an explicit manual GUI checklist.
• No unrelated modifications; commit verified work locally and link implementation PR/commit when published.

Linked implementation issues

Release gate and active toolkit

• [P0] Complete physical Finder and Settings validation for compression + helper IPC #3 — P0: Physical Finder, Settings, compression and authenticated IPC validation
• [Phase 2] Audit and finish PDF, image, metadata, and Finder utilities #2 — P1: Audit/finish Phase 2 PDF and image utilities, mixed merge, OCR, metadata, Copy As and rename

Phase 3 — Reliable background work

• [Phase 3] Background operation center: queue, progress, cancellation, and retry #4 — P1: Background job queue, progress, cancellation and retry
• [Phase 3] Action history and safe undo for reversible Finder operations #5 — P1: Action history and safe undo (builds on [Phase 3] Background operation center: queue, progress, cancellation, and retry #4)

Power-user enhancements

• [Enhancement] Before/after preview for image and PDF compression #6 — P2: Image/PDF original-vs-output quality comparison
• [Enhancement] ZIP archive inspection and safe selective extraction #7 — P2: ZIP inspection and safe selective extraction
• [Enhancement] Find duplicate files using size filters and streamed hashes #8 — P2: Duplicate detection with full-file hashing
• [Enhancement] Favorite copy/move destinations in Finder #9 — P2: Favorite copy/move destinations

Phase 4 — Automation

• [Phase 4] Safe custom Finder actions, macOS Shortcuts, and keyboard access #10 — P2: Custom Finder actions, macOS Shortcuts and keyboard access
• [Phase 4] Saved recipes: reusable non-destructive batch pipelines #11 — P3: Saved multi-step non-destructive recipes (after [Phase 3] Background operation center: queue, progress, cancellation, and retry #4 and [Phase 4] Safe custom Finder actions, macOS Shortcuts, and keyboard access #10)
• [Phase 4] Optional watched folders with explicit opt-in automation rules #12 — P3: Optional watched folders (after [Phase 3] Background operation center: queue, progress, cancellation, and retry #4 and ideally [Phase 4] Saved recipes: reusable non-destructive batch pipelines #11)

Performance, native polish, and release

• [Quality] Scale Finder IPC and selections while keeping menus instant #13 — P1: Scale Finder selections and secure IPC; benchmark menu latency
• [Quality] Native macOS polish, accessibility, and consistent interaction design #14 — P1/P2: Consistent macOS interface, accessibility and keyboard operation
• [Release] Documentation, regression gates, packaging, signing, and distribution readiness #15 — P2: Docs, security/privacy, packaging, optional-codec dependencies and release readiness

Suggested dependency order

#3 → #2 audit → #13 → #4 → #5 → #14 → #15 for a robust daily driver. The P2/P3 enhancements are optional; #6–#10 can be selected based on actual needs. Then #11 and finally #12.

Status caution: All checkboxes start unchecked. Verify the current local implementation and any ongoing agent work before marking a feature done or creating additional duplicate issues.