fix(telemetry,client): report background sync ping and use dynamic test timestamps

backend/tests/test_telemetry.py

@@ -145,6 +145,9 @@ def test_telemetry_api_routes(client):
     headers = {"Authorization": f"Bearer {token}"}
 
     # 2. Ingest telemetry batch
+    now = datetime.now(timezone.utc)
+    started_at = (now - timedelta(minutes=5)).strftime("%Y-%m-%dT%H:%M:%SZ")
+    completed_at = (now - timedelta(minutes=4)).strftime("%Y-%m-%dT%H:%M:%SZ")
     payload = {
         "events": [
             {
@@ -164,8 +167,8 @@ def test_telemetry_api_routes(client):
                 "client_type": "desktop-macos",
                 "client_version": "1.3.2",
                 "device_name": "TestMac",
-                "started_at": "2026-09-16T21:00:00Z",
-                "completed_at": "2026-09-16T21:01:00Z",
+                "started_at": started_at,
+                "completed_at": completed_at,
                 "duration_ms": 60000,
                 "status": "failed",
                 "files_scanned": 100,

client-tauri/src-tauri/src/lib.rs

@@ -710,6 +710,8 @@ fn spawn_background_sync_loop(app: tauri::AppHandle) {
                             client.set_refresh_token(Some(refresh_token));
                         }
                         let result = sync::run_sync(&mut client, &root);
+                        let sync_ok = result.is_ok();
+                        let last_sync_at = chrono::Utc::now().to_rfc3339();
                         match &result {
                             Ok((bytes_downloaded, bytes_uploaded, warning)) => {
                                 if let Some(msg) = warning {
@@ -731,6 +733,9 @@ fn spawn_background_sync_loop(app: tauri::AppHandle) {
                                 update_tray_status(&app_handle, "error", Some(e));
                             }
                         }
+                        if let Err(e) = client.client_ping(Some(sync_ok), Some(last_sync_at)) {
+                            log::warn!("client_ping failed: {}", e);
+                        }
                         let _ = app_handle.emit("sync-status", sync::get_sync_status_payload());
                     }
                 }

openspec/changes/fix-background-sync-ping-and-telemetry-test/.openspec.yaml

@@ -0,0 +1,2 @@
+schema: spec-driven
+created: 2026-11-09

openspec/changes/fix-background-sync-ping-and-telemetry-test/design.md

@@ -0,0 +1,48 @@
+## Context
+
+See `proposal.md` for motivation.
+
+In `client-tauri/src-tauri/src/lib.rs`:
+- Manual sync triggered from GUI (`run_sync`) records `sync_ok` and `last_sync_at` and dispatches `client.client_ping(Some(sync_ok), Some(last_sync_at))`.
+- Periodic background sync (`spawn_background_sync_loop`) runs the same `sync::run_sync(&mut client, &root)` and updates local UI state, but omitted the call to `client.client_ping`.
+
+In `backend/tests/test_telemetry.py`:
+- `test_telemetry_api_routes` seeded a summary with `"started_at": "2026-09-16T21:00:00Z"`.
+- `app.telemetry.service.ingest_telemetry_batch` invokes `prune_telemetry_records`, which deletes any summary older than `now - timedelta(days=30)`.
+- When tests execute >30 days past September 16, 2026, the newly ingested summary is immediately deleted during ingestion, causing assertions to fail.
+
+## Goals / Non-Goals
+
+**Goals:**
+- Unify sync outcome reporting across manual and background synchronization loops in `client-tauri`.
+- Make telemetry test timestamps dynamic and resilient to arbitrary future test run dates.
+- Keep all fixes strictly scoped, non-breaking, and with zero changes to existing public API schemas.
+
+**Non-Goals:**
+- Changing the retention window duration (30 days remains the server default).
+- Adding retry queues for `client_ping` (pings remain best-effort, subsequent sync cycles naturally update server state).
+
+## Decisions
+
+### 1. Replicate `client_ping` invocation pattern in `spawn_background_sync_loop`
+- **Choice**: Right after `sync::run_sync(&mut client, &root)` completes in `spawn_background_sync_loop`, capture:
+  ```rust
+  let sync_ok = result.is_ok();
+  let last_sync_at = chrono::Utc::now().to_rfc3339();
+  ```
+  and invoke:
+  ```rust
+  if let Err(e) = client.client_ping(Some(sync_ok), Some(last_sync_at)) {
+      log::warn!("client_ping failed: {}", e);
+  }
+  ```
+- **Rationale**: Matches the behavior of `run_sync` exactly. Any failure to ping is logged at `WARN` level and does not terminate the background loop.
+
+### 2. Dynamic UTC timestamps in test fixture
+- **Choice**: Use Python's `datetime.now(timezone.utc)` to compute `started_at` (5 minutes ago) and `completed_at` (4 minutes ago) formatted as ISO 8601 strings (`.strftime("%Y-%m-%dT%H:%M:%SZ")`).
+- **Rationale**: Matches the pattern already established in `test_sync_summary_and_diagnostic_event_crud_and_pruning`, ensuring fixtures never expire regardless of calendar year.
+
+## Risks / Trade-offs
+
+- **[Risk]** Network error during client ping in background thread.
+  - *Mitigation*: Handled as non-fatal with `log::warn!`, identical to manual sync. Next background interval (60s) will attempt sync and ping again.

openspec/changes/fix-background-sync-ping-and-telemetry-test/proposal.md

@@ -0,0 +1,26 @@
+## Why
+
+Two concrete bugs currently affect BrandyBox's telemetry and monitoring subsystems:
+1. In `client-tauri`, `spawn_background_sync_loop` executes periodic background synchronization runs but completely omits the `client.client_ping(Some(sync_ok), Some(last_sync_at))` call that is performed during manual sync (`run_sync`). Consequently, central server monitoring (`GET /api/admin/clients` and `brandybox-doctor --summary`) displays active clients as disconnected or never synchronized unless manual synchronization is triggered in the GUI.
+2. In `backend/tests/test_telemetry.py`, `test_telemetry_api_routes` inserts a hardcoded static timestamp (`2026-09-16T21:00:00Z`). Because `ingest_telemetry_batch` enforces a 30-day retention cleanup via `prune_telemetry_records`, any test run more than 30 days after September 16, 2026 immediately deletes the newly ingested summary, causing the test suite assertion `assert any(s["trace_id"] == "sync-api-test-01" for s in summaries)` to fail.
+
+Fixing these ensures accurate client observability in the central monitoring dashboard and stabilizes the backend automated test suite.
+
+## What Changes
+
+- **Desktop Client Background Ping Telemetry**: Update `spawn_background_sync_loop` in `client-tauri/src-tauri/src/lib.rs` to compute `sync_ok` and `last_sync_at`, invoking `client.client_ping(Some(sync_ok), Some(last_sync_at))` upon completion of each background sync run.
+- **Dynamic Telemetry Test Timestamps**: In `backend/tests/test_telemetry.py`, replace static September 2026 timestamp strings with dynamic UTC timestamps relative to `datetime.now(timezone.utc)` so ingested records remain within the 30-day retention window during test assertions.
+
+## Capabilities
+
+### New Capabilities
+<!-- None -->
+
+### Modified Capabilities
+- `central-telemetry`: Clarify requirement that client ping telemetry (`POST /api/clients/ping`) SHALL be dispatched upon completion of both manual and automatic background synchronization cycles.
+
+## Impact
+
+- `client-tauri/src-tauri/src/lib.rs`: Background sync loop dispatches `client_ping`.
+- `backend/tests/test_telemetry.py`: Test fixtures generate valid dynamic timestamps.
+- Admin dashboard (`/api/admin/clients`) and CLI (`brandybox-doctor --summary`): Accurately reflect active client synchronization activity from background daemons.

openspec/changes/fix-background-sync-ping-and-telemetry-test/specs/central-telemetry/spec.md

@@ -0,0 +1,12 @@
+## ADDED Requirements
+
+### Requirement: Client ping telemetry upon cycle completion
+The client SHALL report its client type, client version, synchronization outcome, and last sync timestamp to the central backend (`POST /api/clients/ping`) upon concluding each synchronization cycle, whether triggered manually by the user or executed automatically in the background daemon loop.
+
+#### Scenario: Background synchronization cycle concludes
+- **WHEN** an automatic periodic background synchronization cycle concludes (whether successful, with warnings, or failed)
+- **THEN** the client dispatches a `POST /api/clients/ping` request containing `last_sync_ok` and `last_sync_at` to record active client connection and sync state on the backend.
+
+#### Scenario: Manual synchronization cycle concludes
+- **WHEN** a user-initiated synchronization cycle concludes (whether successful, with warnings, or failed)
+- **THEN** the client dispatches a `POST /api/clients/ping` request containing `last_sync_ok` and `last_sync_at` to record active client connection and sync state on the backend.

openspec/changes/fix-background-sync-ping-and-telemetry-test/tasks.md

@@ -0,0 +1,13 @@
+## 1. Backend Telemetry Test Fixture
+
+- [x] 1.1 Update `test_telemetry_api_routes` in `backend/tests/test_telemetry.py` to use dynamic UTC timestamps for `started_at` and `completed_at` relative to `datetime.now(timezone.utc)`, and verify `pytest backend/tests/test_telemetry.py` passes.
+
+## 2. Desktop Client Background Sync Telemetry
+
+- [x] 2.1 In `client-tauri/src-tauri/src/lib.rs`, capture `sync_ok` and `last_sync_at` after `sync::run_sync(&mut client, &root)` and invoke `client.client_ping(Some(sync_ok), Some(last_sync_at))` in `spawn_background_sync_loop`.
+- [x] 2.2 Verify client library compiles and tests pass with `cargo test --manifest-path client-tauri/src-tauri/Cargo.toml`.
+
+## 3. Full System Verification
+
+- [x] 3.1 Run backend pytest suite with `pytest backend` and verify all tests pass.
+- [x] 3.2 Run autonomous sync e2e suite with `pytest tests/e2e/test_run_autonomous_sync.py` and verify all tests pass.