internal/server/http/pending_drain.go

@@ -81,14 +81,15 @@ func (s *Server) drainOne(ctx context.Context, conn *ws.Conn, p store.PendingRun
 		s.abandonPending(ctx, p, "retry_max exceeded")
 		return
 	}
-	jobID := s.dispatchBackupForGroup(ctx, conn, p.HostID, p.ScheduleID, g, p.ScheduledAt)
+	// Calls dispatchBackupForGroupCore (not dispatchBackupForGroup) so a
+	// failed Send doesn't double-enqueue: dispatchBackupForGroup's
+	// enqueue-on-failure path would create a NEW pending_runs row while
+	// this function already bumps the EXISTING row via
+	// BumpPendingRunAttempt, producing geometric duplicates on repeated
+	// failures.
+	jobID, _ := s.dispatchBackupForGroupCore(ctx, conn, p.HostID, p.ScheduleID, g, p.ScheduledAt)
 	if jobID == "" {
 		// Send failed again. Bump attempt with exponential backoff.
-		// Note: dispatchBackupForGroup's failure path *also* enqueues a
-		// fresh pending_runs row (G1.1). That's a duplicate, but harmless:
-		// it'll be drained the same way and either succeed or hit
-		// retry_max alongside this one. The bump below preserves this
-		// row's history (attempt count, last error) for forensics.
 		baseBackoff := time.Duration(g.RetryBackoffSeconds) * time.Second
 		if baseBackoff <= 0 {
 			baseBackoff = 60 * time.Second

internal/server/http/pending_drain_test.go

@@ -255,11 +255,13 @@ func TestDrainPendingBumpsOnSendFailure(t *testing.T) {
 		Attempt: 1, NextAttemptAt: now.Add(-time.Second), ScheduledAt: now.Add(-time.Minute),
 	})
 
-	// The original row was bumped (attempt=2) — the G1.1 path may have
-	// also enqueued a duplicate row from inside dispatchBackupForGroup's
-	// failed Send. So we expect exactly the original row updated, plus
-	// possibly one duplicate. Either way: pending count >= 1, no row
-	// deleted, and the original row's attempt bumped to 2.
+	// The original row must be bumped to attempt=2 with a non-empty
+	// last_error. Critically, NO duplicate row should have been created:
+	// drainOne calls dispatchBackupForGroupCore (not dispatchBackupForGroup)
+	// so the enqueue-on-failure path is bypassed and the count stays at 1.
+	if n := countPendingForHost(t, st, hostID); n != 1 {
+		t.Errorf("pending rows after send failure: got %d, want 1 (no duplicate enqueue)", n)
+	}
 	var attempt int
 	var lastErr string
 	if err := st.DB().QueryRow(
@@ -273,12 +275,6 @@ func TestDrainPendingBumpsOnSendFailure(t *testing.T) {
 	if lastErr == "" {
 		t.Errorf("last_error empty after bump")
 	}
-	// No successful backup job persisted via DrainPending.
-	// (dispatchBackupForGroup *does* create a job row before attempting
-	// the send and leaves it on send-failure; that row exists. The
-	// "successful job" we care about would be one that wasn't followed
-	// by an enqueue — there aren't any here. Asserting on the bump is
-	// the cleaner signal.)
 }
 
 func TestDrainPendingDropsRowsForGoneSchedule(t *testing.T) {

internal/server/http/schedule_push.go

@@ -164,15 +164,19 @@ func (s *Server) dispatchScheduledJob(ctx context.Context, hostID string, conn *
 	}
 }
 
-// dispatchBackupForGroup builds and sends a single backup command.run
-// envelope on conn for the given group. Persists the job row first so
-// the live log viewer can subscribe to it.
-// dispatchBackupForGroup persists a backup job row, sends the
-// command.run envelope to the agent, and audit-logs the dispatch.
-// Returns the persisted job ID on success, or "" on any failure
-// (failures are slog.Warn-ed). Callers may use the returned ID to,
-// e.g., redirect the UI to the live job log.
-func (s *Server) dispatchBackupForGroup(ctx context.Context, conn *ws.Conn, hostID, scheduleID string, g *store.SourceGroup, scheduledAt time.Time) string {
+// dispatchBackupForGroupCore persists a backup job row, marshals and
+// sends the command.run envelope, and audit-logs the dispatch. It does
+// NOT enqueue a PendingRun on failure — that responsibility belongs to
+// the caller when appropriate.
+//
+// Returns (jobID, nil) on success. Returns ("", err) on any failure;
+// the error is also slog.Warn-ed inside this function so callers don't
+// need to log it again.
+//
+// Used by both dispatchBackupForGroup (schedule.fire path, which adds
+// enqueue-on-failure) and drainOne (which handles failure via
+// BumpPendingRunAttempt on the existing row, avoiding double-enqueue).
+func (s *Server) dispatchBackupForGroupCore(ctx context.Context, conn *ws.Conn, hostID, scheduleID string, g *store.SourceGroup, scheduledAt time.Time) (string, error) {
 	jobID := ulid.Make().String()
 	now := time.Now().UTC()
 	scheduleRef := scheduleID
@@ -186,7 +190,7 @@ func (s *Server) dispatchBackupForGroup(ctx context.Context, conn *ws.Conn, host
 	}); err != nil {
 		slog.Warn("schedule.fire: persist job", "host_id", hostID,
 			"schedule_id", scheduleID, "group", g.Name, "err", err)
-		return ""
+		return "", err
 	}
 	// Backup ignores RetentionPolicy — the forget cadence lives on
 	// host_repo_maintenance and is driven by the server-side ticker
@@ -201,36 +205,17 @@ func (s *Server) dispatchBackupForGroup(ctx context.Context, conn *ws.Conn, host
 	if err != nil {
 		slog.Warn("schedule.fire: marshal command.run",
 			"host_id", hostID, "schedule_id", scheduleID, "err", err)
-		return ""
+		return "", err
 	}
 	sendCtx, cancel := context.WithTimeout(ctx, 5*time.Second)
 	defer cancel()
 	if err := conn.Send(sendCtx, env); err != nil {
-		slog.Warn("schedule.fire: send command.run failed, queueing for retry",
+		slog.Warn("schedule.fire: send command.run failed",
 			"host_id", hostID, "schedule_id", scheduleID, "group", g.Name, "err", err)
-		backoff := time.Duration(g.RetryBackoffSeconds) * time.Second
-		if backoff <= 0 {
-			backoff = 60 * time.Second
-		}
-		if enqueueErr := s.deps.Store.EnqueuePendingRun(ctx, &store.PendingRun{
-			ID:            ulid.Make().String(),
-			ScheduleID:    scheduleID,
-			SourceGroupID: g.ID,
-			HostID:        hostID,
-			Attempt:       1,
-			NextAttemptAt: time.Now().UTC().Add(backoff),
-			ScheduledAt:   scheduledAt,
-			LastError:     err.Error(),
-		}); enqueueErr != nil {
-			slog.Warn("schedule.fire: enqueue pending run failed",
-				"host_id", hostID, "schedule_id", scheduleID, "group", g.Name, "err", enqueueErr)
-		}
-		// The job row was already persisted earlier in this function — leave
-		// it in `queued` status. The drainer will re-dispatch (creating a
-		// new job row) and the orphaned queued row stays for forensic
-		// visibility. Don't delete it: the audit trail still wants to know
-		// "we tried and the wire was wedged."
-		return ""
+		// The job row was already persisted — leave it in `queued` status.
+		// The drainer will re-dispatch (creating a new job row) and the
+		// orphaned queued row stays for forensic visibility.
+		return "", err
 	}
 	_ = s.deps.Store.AppendAudit(ctx, store.AuditEntry{
 		ID:         ulid.Make().String(),
@@ -243,5 +228,37 @@ func (s *Server) dispatchBackupForGroup(ctx context.Context, conn *ws.Conn, host
 	slog.Info("schedule.fire: dispatched backup",
 		"host_id", hostID, "schedule_id", scheduleID,
 		"group", g.Name, "job_id", jobID, "scheduled_at", scheduledAt)
-	return jobID
+	return jobID, nil
+}
+
+// dispatchBackupForGroup is the schedule.fire entry point. Wraps
+// dispatchBackupForGroupCore with enqueue-on-failure: a failed Send
+// queues a fresh PendingRun for the drainer to retry later.
+//
+// Returns the persisted job ID on success, or "" on any failure.
+func (s *Server) dispatchBackupForGroup(ctx context.Context, conn *ws.Conn, hostID, scheduleID string, g *store.SourceGroup, scheduledAt time.Time) string {
+	jobID, err := s.dispatchBackupForGroupCore(ctx, conn, hostID, scheduleID, g, scheduledAt)
+	if err == nil {
+		return jobID
+	}
+	// Send (or an earlier step) failed — err was already logged inside
+	// the core. Enqueue a fresh PendingRun for the drainer to retry.
+	backoff := time.Duration(g.RetryBackoffSeconds) * time.Second
+	if backoff <= 0 {
+		backoff = 60 * time.Second
+	}
+	if enqueueErr := s.deps.Store.EnqueuePendingRun(ctx, &store.PendingRun{
+		ID:            ulid.Make().String(),
+		ScheduleID:    scheduleID,
+		SourceGroupID: g.ID,
+		HostID:        hostID,
+		Attempt:       1,
+		NextAttemptAt: time.Now().UTC().Add(backoff),
+		ScheduledAt:   scheduledAt,
+		LastError:     err.Error(),
+	}); enqueueErr != nil {
+		slog.Warn("schedule.fire: enqueue pending run failed",
+			"host_id", hostID, "schedule_id", scheduleID, "group", g.Name, "err", enqueueErr)
+	}
+	return ""
 }