---
phase: 25-file-system
plan: 07
subsystem: api
tags: [placeholder, agent-generated, manifest, markdown, chat-files]

requires:
  - phase: 25-01
    provides: chatFileService with create/getById/createReference methods
  - phase: 25-06
    provides: git-file-service with storageDir pattern (on separate worktree; storageDir import added here)

provides:
  - placeholderService with addEntry/replaceEntry/listEntries managing PLACEHOLDERS.md
  - chatFileService.markAsPlaceholder method
  - POST /files/:fileId/replace endpoint for placeholder replacement
  - Agent-generated file tracking in PLACEHOLDERS.md manifest

affects: [25-06, future-agent-file-generation]

tech-stack:
  added: []
  patterns:
    - placeholderService reads/writes PLACEHOLDERS.md markdown tables
    - fire-and-forget phSvc.addEntry() on upload (non-blocking)
    - replace endpoint updates manifest + creates reference chain atomically

key-files:
  created:
    - server/src/services/placeholder-service.ts
  modified:
    - server/src/services/chat-files.ts
    - server/src/routes/chat-files.ts
    - packages/shared/src/types/chat.ts
    - packages/shared/src/index.ts
    - .planning/REQUIREMENTS.md

key-decisions:
  - "placeholderService reads/writes PLACEHOLDERS.md using regex row parser to avoid markdown deps"
  - "addEntry is fire-and-forget (.catch(() => {})) — response not blocked by file I/O"
  - "replaceEntry is awaited in /replace endpoint — manifest must be consistent before response"
  - "resolveDefaultStorageDir() used for projectDir path — consistent with git-file-service pattern"

patterns-established:
  - "Placeholder manifest: Active Placeholders and Replaced markdown tables in PLACEHOLDERS.md per project dir"
  - "Replace endpoint: phSvc.replaceEntry + fileSvc.createReference for atomically updating both manifest and DB"

requirements-completed: [FILE-08, FILE-11]

duration: 10min
completed: 2026-04-02
---

# Phase 25 Plan 07: Agent-Generated File Support and Placeholder Tracking Summary

**PLACEHOLDERS.md manifest service with addEntry/replaceEntry and POST /files/:fileId/replace endpoint wiring agent-generated uploads to per-project markdown manifests**

## Performance

- **Duration:** ~10 min
- **Started:** 2026-04-02T00:09:00Z
- **Completed:** 2026-04-02T00:12:49Z
- **Tasks:** 2
- **Files modified:** 5

## Accomplishments
- Created `placeholder-service.ts` with full PLACEHOLDERS.md markdown table management (addEntry, replaceEntry, listEntries)
- Added `markAsPlaceholder` method to `chatFileService` for DB-level placeholder categorization
- Wired agent_generated + project-scoped uploads to automatically update PLACEHOLDERS.md
- Added `POST /files/:fileId/replace` endpoint that updates manifest and creates DB reference chain
- Marked FILE-08 and FILE-11 Complete in REQUIREMENTS.md

## Task Commits

Each task was committed atomically:

1. **Task 1: Create placeholderService and add markAsPlaceholder method** - `0a80659c` (feat)
2. **Task 2: Add placeholder and agent-generated file routes** - `2a4037ca` (feat)

## Files Created/Modified
- `server/src/services/placeholder-service.ts` - PLACEHOLDERS.md manifest management service (161 lines)
- `server/src/services/chat-files.ts` - Added markAsPlaceholder method
- `server/src/routes/chat-files.ts` - Added phSvc import, agent_generated tracking, /replace endpoint
- `packages/shared/src/types/chat.ts` - Added ChatPlaceholderEntry interface
- `packages/shared/src/index.ts` - Exported ChatPlaceholderEntry
- `.planning/REQUIREMENTS.md` - Marked FILE-08 and FILE-11 Complete

## Decisions Made
- Used regex row parser (`/^\|\s*(.+?)\s*\|\s*(.+?)\s*\|\s*(.+?)\s*\|$/`) to parse markdown tables — no external markdown deps needed
- `addEntry` is fire-and-forget (non-blocking) to avoid blocking upload response
- `replaceEntry` is awaited in the replace endpoint for manifest consistency before response
- Used `resolveDefaultStorageDir()` for project dir base path, consistent with 25-06 storageDir pattern
- `git-file-service.ts` not present on this branch (in 25-06 worktree); storageDir import added here for placeholder path only

## Deviations from Plan

None - plan executed exactly as written.

## Issues Encountered
- `git-file-service.ts` not present on current branch (it's in the 25-06 worktree). Per the important_context note, proceeded with placeholder-service implementation and imported `resolveDefaultStorageDir` directly for the project path computation. No blocking impact.

## Next Phase Readiness
- PLACEHOLDERS.md manifest management complete; any agent that uploads with source=agent_generated and projectId will auto-track
- Replace endpoint ready for agent workflows that upgrade placeholder assets to final outputs
- FILE-08 and FILE-11 marked complete

---
*Phase: 25-file-system*
*Completed: 2026-04-02*