diff --git a/plugins/logging/sweeper_test.go b/plugins/logging/sweeper_test.go
new file mode 100644
index 0000000000..de635480fc
--- /dev/null
+++ b/plugins/logging/sweeper_test.go
@@ -0,0 +1,187 @@
+package logging
+
+import (
+	"strings"
+	"testing"
+	"time"
+)
+
+// newTestPlugin returns a minimal LoggerPlugin suitable for sweeper unit tests.
+// It wires up a real SQLite store (via newTestStore) and a buffered write queue
+// so that enqueueLogEntry works without a running batchWriter goroutine.
+func newTestPlugin(t *testing.T) *LoggerPlugin {
+	t.Helper()
+	store := newTestStore(t)
+	return &LoggerPlugin{
+		store:      store,
+		logger:     testLogger{},
+		writeQueue: make(chan *writeQueueEntry, writeQueueCapacity),
+	}
+}
+
+// drainQueue reads all entries currently buffered in the plugin's writeQueue
+// and returns them as a slice.
+func drainQueue(p *LoggerPlugin) []*writeQueueEntry {
+	var out []*writeQueueEntry
+	for {
+		select {
+		case e := <-p.writeQueue:
+			out = append(out, e)
+		default:
+			return out
+		}
+	}
+}
+
+// TestSweeperFlushesOrphanedPendingLogsEntry verifies that cleanupStalePendingLogs
+// enqueues a synthesized error row before deleting a stale pendingLogsEntries
+// entry whose TTL has expired.
+func TestSweeperFlushesOrphanedPendingLogsEntry(t *testing.T) {
+	plugin := newTestPlugin(t)
+
+	requestID := "req-orphan-1"
+	staleTime := time.Now().Add(-(pendingLogTTL + time.Minute))
+
+	pending := &PendingLogData{
+		RequestID: requestID,
+		Timestamp: staleTime,
+		CreatedAt: staleTime,
+		InitialData: &InitialLogData{
+			Object:   "chat_completion",
+			Provider: "openai",
+			Model:    "gpt-4o",
+		},
+	}
+	plugin.pendingLogsEntries.Store(requestID, pending)
+
+	plugin.cleanupStalePendingLogs()
+
+	// The entry must be removed from the in-memory map.
+	if _, ok := plugin.pendingLogsEntries.Load(requestID); ok {
+		t.Fatal("expected pendingLogsEntries to be cleared after TTL eviction")
+	}
+
+	// Exactly one write must have been enqueued.
+	entries := drainQueue(plugin)
+	if len(entries) != 1 {
+		t.Fatalf("expected 1 write queue entry, got %d", len(entries))
+	}
+
+	log := entries[0].log
+	if log == nil {
+		t.Fatal("expected non-nil log entry in write queue")
+	}
+	if log.ID != requestID {
+		t.Fatalf("log.ID = %q, want %q", log.ID, requestID)
+	}
+	if log.Status != "error" {
+		t.Fatalf("log.Status = %q, want %q", log.Status, "error")
+	}
+	if !strings.Contains(log.ErrorDetails, "abandoned") {
+		t.Fatalf("log.ErrorDetails = %q, expected it to mention abandoned", log.ErrorDetails)
+	}
+	if log.Provider != "openai" {
+		t.Fatalf("log.Provider = %q, want %q", log.Provider, "openai")
+	}
+	if log.Model != "gpt-4o" {
+		t.Fatalf("log.Model = %q, want %q", log.Model, "gpt-4o")
+	}
+}
+
+// TestSweeperDoesNotFlushFreshPendingLogsEntry verifies that a pendingLogsEntries
+// entry that has not yet exceeded its TTL is left untouched.
+func TestSweeperDoesNotFlushFreshPendingLogsEntry(t *testing.T) {
+	plugin := newTestPlugin(t)
+
+	requestID := "req-fresh-1"
+	pending := &PendingLogData{
+		RequestID: requestID,
+		Timestamp: time.Now(),
+		CreatedAt: time.Now(),
+		InitialData: &InitialLogData{
+			Object:   "chat_completion",
+			Provider: "openai",
+			Model:    "gpt-4o",
+		},
+	}
+	plugin.pendingLogsEntries.Store(requestID, pending)
+
+	plugin.cleanupStalePendingLogs()
+
+	// The entry must still be present.
+	if _, ok := plugin.pendingLogsEntries.Load(requestID); !ok {
+		t.Fatal("expected fresh pendingLogsEntries entry to survive TTL sweep")
+	}
+
+	// No writes should have been enqueued.
+	entries := drainQueue(plugin)
+	if len(entries) != 0 {
+		t.Fatalf("expected no write queue entries for fresh entry, got %d", len(entries))
+	}
+}
+
+// TestSweeperFlushesMultipleOrphanedEntries verifies that all stale entries
+// are individually flushed when the sweeper runs.
+func TestSweeperFlushesMultipleOrphanedEntries(t *testing.T) {
+	plugin := newTestPlugin(t)
+
+	staleTime := time.Now().Add(-(pendingLogTTL + time.Minute))
+	ids := []string{"req-multi-1", "req-multi-2", "req-multi-3"}
+	for _, id := range ids {
+		plugin.pendingLogsEntries.Store(id, &PendingLogData{
+			RequestID: id,
+			Timestamp: staleTime,
+			CreatedAt: staleTime,
+			InitialData: &InitialLogData{
+				Object:   "chat_completion",
+				Provider: "openai",
+				Model:    "gpt-4o",
+			},
+		})
+	}
+
+	plugin.cleanupStalePendingLogs()
+
+	// All entries must be evicted.
+	for _, id := range ids {
+		if _, ok := plugin.pendingLogsEntries.Load(id); ok {
+			t.Fatalf("expected entry %q to be evicted", id)
+		}
+	}
+
+	// One write per entry.
+	entries := drainQueue(plugin)
+	if len(entries) != len(ids) {
+		t.Fatalf("expected %d write queue entries, got %d", len(ids), len(entries))
+	}
+	for _, e := range entries {
+		if e.log.Status != "error" {
+			t.Fatalf("entry %q: status = %q, want error", e.log.ID, e.log.Status)
+		}
+	}
+}
+
+// TestSweeperStalePendingLogsToInjectEvictedWithoutPanic verifies that the
+// pendingLogsToInject cleanup still runs without error when stale entries are
+// present. The inject entries are not DB-flushed (they lack a requestID
+// anchor) so this test focuses on panic-free eviction only.
+func TestSweeperStalePendingLogsToInjectEvictedWithoutPanic(t *testing.T) {
+	plugin := newTestPlugin(t)
+
+	staleTime := time.Now().Add(-(pendingLogTTL + time.Minute))
+	plugin.pendingLogsToInject.Store("trace-stale", &pendingInjectEntries{
+		createdAt: staleTime,
+	})
+	plugin.pendingLogsToInject.Store("trace-fresh", &pendingInjectEntries{
+		createdAt: time.Now(),
+	})
+
+	plugin.cleanupStalePendingLogs()
+
+	if _, ok := plugin.pendingLogsToInject.Load("trace-stale"); ok {
+		t.Fatal("expected stale pendingLogsToInject entry to be evicted")
+	}
+	if _, ok := plugin.pendingLogsToInject.Load("trace-fresh"); !ok {
+		t.Fatal("expected fresh pendingLogsToInject entry to survive TTL sweep")
+	}
+}
diff --git a/plugins/logging/writer.go b/plugins/logging/writer.go
index fe34bc4a8f..c744e55c7c 100644
--- a/plugins/logging/writer.go
+++ b/plugins/logging/writer.go
@@ -175,14 +175,26 @@ func (p *LoggerPlugin) processBatch(batch []*writeQueueEntry) {
 // cleanupStalePendingLogs removes entries from pendingLogs that have been
 // waiting longer than pendingLogTTL. This handles cases where PostLLMHook
 // never fires for a request (e.g., request was cancelled before reaching the provider).
+//
+// Before evicting a pendingLogsEntries entry the function writes a synthesized
+// error row to the DB so operators can observe the abandoned request in the audit
+// trail. Without this flush the request vanishes with no trace in the logs table.
 func (p *LoggerPlugin) cleanupStalePendingLogs() {
 	cutoff := time.Now().Add(-pendingLogTTL)
 	p.pendingLogsEntries.Range(func(key, value any) bool {
-		if pending, ok := value.(*PendingLogData); ok {
-			if pending.CreatedAt.Before(cutoff) {
-				p.pendingLogsEntries.Delete(key)
-			}
+		pending, ok := value.(*PendingLogData)
+		if !ok {
+			return true
+		}
+		if !pending.CreatedAt.Before(cutoff) {
+			return true
 		}
+		p.logger.Warn("evicting orphaned pending log entry %s (created %s, PostLLMHook never fired)", pending.RequestID, pending.CreatedAt.Format(time.RFC3339))
+		entry := buildInitialLogEntry(pending)
+		entry.Status = "error"
+		entry.ErrorDetails = `{"message":"abandoned: PostLLMHook never fired (TTL eviction)"}`
+		p.enqueueLogEntry(entry, nil)
+		p.pendingLogsEntries.Delete(key)
 		return true
 	})
 	p.pendingLogsToInject.Range(func(key, value any) bool {