chore(conductor): Add new track 'Testing Infrastructure'

conductor/tracks.md

@@ -26,3 +26,8 @@ This file tracks all major tracks for the project. Each track has its own detail
 
 - [x] **Track: Fix SyntaxError: Invalid weekday string: [object Object] by implementing a generic recursive RRULE formatter.**
   *Link: [./tracks/rrule_generic_formatter_20260219/](./tracks/rrule_generic_formatter_20260219/)*
+
+---
+
+- [ ] **Track: Implement Playwright and Dockerized testing infrastructure with real ICS data samples.**
+  *Link: [./tracks/testing_infrastructure_20260219/](./tracks/testing_infrastructure_20260219/)*

conductor/tracks/testing_infrastructure_20260219/index.md

@@ -0,0 +1,5 @@
+# Track testing_infrastructure_20260219 Context
+
+- [Specification](./spec.md)
+- [Implementation Plan](./plan.md)
+- [Metadata](./metadata.json)

conductor/tracks/testing_infrastructure_20260219/metadata.json

@@ -0,0 +1,8 @@
+{
+  "track_id": "testing_infrastructure_20260219",
+  "type": "chore",
+  "status": "new",
+  "created_at": "2026-02-19T00:00:00Z",
+  "updated_at": "2026-02-19T00:00:00Z",
+  "description": "Implement Playwright and Dockerized testing infrastructure with real ICS data samples."
+}

conductor/tracks/testing_infrastructure_20260219/plan.md

@@ -0,0 +1,27 @@
+# Implementation Plan - Testing Infrastructure
+
+## Phase 1: Environment & Mock Server
+- [ ] Task: Scaffold Docker environment
+    - [ ] Create test_data/ directory.
+    - [ ] Create docker-compose.test.yml with SilverBullet and an Nginx container serving test_data/.
+- [ ] Task: Integration Test Scaffolding
+    - [ ] Create tests/integration_test.ts that uses the actual ts-ics parser on files in test_data/.
+- [ ] Task: Conductor - User Manual Verification 'Environment & Mock Server' (Protocol in workflow.md)
+
+## Phase 2: Playwright E2E Setup
+- [ ] Task: Initialize Playwright
+    - [ ] Setup Playwright with necessary configurations for Docker (headless, CI mode).
+- [ ] Task: Implement sync smoke test
+    - [ ] Create tests/e2e/sync.spec.ts.
+    - [ ] Automate login, plug installation (icalendar.plug.js), and triggering the "iCalendar: Sync" command.
+    - [ ] Implement console listener to fail on Error or TypeError.
+- [ ] Task: Conductor - User Manual Verification 'Playwright E2E Setup' (Protocol in workflow.md)
+
+## Phase 3: Validation & Bug Fix
+- [ ] Task: Verify Infrastructure against current bug
+    - [ ] Add the problematic .ics to test_data/.
+    - [ ] Confirm that E2E and Integration tests fail with Unknown RRULE property 'WORKWEEKSTART'.
+- [ ] Task: Implement Fix for WORKWEEKSTART
+    - [ ] Update RRULE_KEY_MAP in icalendar.ts.
+    - [ ] Run tests again to confirm they pass.
+- [ ] Task: Conductor - User Manual Verification 'Validation & Bug Fix' (Protocol in workflow.md)

conductor/tracks/testing_infrastructure_20260219/spec.md

@@ -0,0 +1,26 @@
+# Specification: Testing Infrastructure (Playwright & Docker)
+
+## Overview
+Our current testing strategy relies on manual mocks that don't capture the complexity of real-world iCalendar data (specifically from Outlook/Office 365). This has led to multiple regressions where object-type RRULE properties cause the plug to fail. This track implements a full E2E and integration testing suite using Docker, Playwright, and real .ics samples.
+
+## Functional Requirements
+- **Dockerized Environment:** A docker-compose.test.yml that spins up:
+    - **SilverBullet:** A clean instance for plug installation.
+    - **Mock ICS Server:** A simple web server serving files from a test_data/ directory.
+- **Playwright E2E Suite:**
+    - **Automation:** Automates logging into SilverBullet, installing the freshly built icalendar.plug.js, and triggering a sync.
+    - **Console Monitoring:** Automatically fails the test if any Error or TypeError is detected in the browser console.
+    - **Index Verification:** Uses SilverBullet syscalls (via Playwright evaluate) or UI queries to verify that the expected number of ical-event objects exist in the index.
+- **Real-Data Integration Tests:** Deno unit tests that parse actual .ics files (e.g. mock_calendar.ics) using the real ts-ics parser before calling expandRecurrences.
+
+## Implementation Steps
+1. Environment Setup: Create docker-compose.test.yml and a test_data/ directory with at least one problematic Outlook .ics file.
+2. Mock Server: Configure a lightweight container (e.g., Nginx or Python) to serve the test_data/.
+3. Playwright Scaffolding: Initialize Playwright and create a tests/sync.spec.ts that handles authentication and plug installation.
+4. Verification Logic: Implement the console-listener and index-counting logic in the test suite.
+5. Smoke Test: Fix the known WORKWEEKSTART error and verify that the new infrastructure catches it if the fix is reverted.
+
+## Acceptance Criteria
+- [ ] A single command (e.g., make test-e2e) builds the plug, starts the containers, and runs the Playwright suite.
+- [ ] The E2E suite successfully identifies the WORKWEEKSTART error when run against the current (buggy) code.
+- [ ] The E2E suite passes after the WORKWEEKSTART fix is applied.