diff --git a/apps/backend/internal/automation/scheduler_test.go b/apps/backend/internal/automation/scheduler_test.go
new file mode 100644
index 0000000000..6f1bb6c140
--- /dev/null
+++ b/apps/backend/internal/automation/scheduler_test.go
@@ -0,0 +1,199 @@
+package automation
+
+import (
+	"context"
+	"encoding/json"
+	"go.uber.org/zap"
+	"testing"
+	"time"
+
+	"github.com/kandev/kandev/internal/common/logger"
+)
+
+// TestFireTrigger_SkippedForConcurrencyCap_UpdatesLastEvaluatedAt guards
+// against the scheduler retrying a scheduled trigger on every check tick
+// once max_concurrent_runs is reached. FireTrigger must record that the
+// trigger was evaluated even when the run itself is skipped, otherwise
+// CronScheduler.shouldFire sees a stale LastEvaluatedAt forever and fires
+// again on the very next tick instead of waiting out the configured
+// interval.
+func TestFireTrigger_SkippedForConcurrencyCap_UpdatesLastEvaluatedAt(t *testing.T) {
+	svc := newTestService(t)
+	ctx := context.Background()
+
+	a := &Automation{
+		WorkspaceID:       "ws-1",
+		Name:              "Daily rebase",
+		WorkflowID:        "wf-1",
+		WorkflowStepID:    "s-1",
+		Enabled:           true,
+		MaxConcurrentRuns: 1,
+	}
+	if err := svc.store.CreateAutomation(ctx, a); err != nil {
+		t.Fatal(err)
+	}
+
+	cfg, _ := json.Marshal(ScheduledTriggerConfig{CronExpression: "@daily"})
+	trig := &AutomationTrigger{AutomationID: a.ID, Type: TriggerTypeScheduled, Config: cfg, Enabled: true}
+	if err := svc.store.CreateTrigger(ctx, trig); err != nil {
+		t.Fatal(err)
+	}
+
+	// Seed an already-active run so the automation sits at its concurrency cap.
+	active := &AutomationRun{
+		AutomationID: a.ID,
+		TriggerID:    trig.ID,
+		TriggerType:  TriggerTypeScheduled,
+		Status:       RunStatusTaskCreated,
+		DedupKey:     "seed-active-run",
+		TriggerData:  json.RawMessage(`{}`),
+	}
+	if err := svc.store.CreateRun(ctx, active); err != nil {
+		t.Fatal(err)
+	}
+
+	if err := svc.FireTrigger(ctx, a.ID, trig.ID, TriggerTypeScheduled, json.RawMessage(`{}`), "scheduled:trig:1"); err != nil {
+		t.Fatalf("FireTrigger returned error for a skip: %v", err)
+	}
+
+	runs, err := svc.store.ListRuns(ctx, a.ID, 10)
+	if err != nil {
+		t.Fatal(err)
+	}
+	skipped := 0
+	for _, r := range runs {
+		if r.Status == RunStatusSkipped {
+			skipped++
+		}
+	}
+	if skipped != 1 {
+		t.Fatalf("expected 1 skipped run, got %d (runs=%+v)", skipped, runs)
+	}
+
+	triggers, err := svc.store.ListTriggers(ctx, a.ID)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if len(triggers) != 1 {
+		t.Fatalf("expected 1 trigger, got %d", len(triggers))
+	}
+	if triggers[0].LastEvaluatedAt == nil {
+		t.Fatal("expected LastEvaluatedAt to be set after a concurrency-cap skip, got nil")
+	}
+}
+
+// TestCronScheduler_DailyTrigger_DoesNotRefireNextTick reproduces the
+// reported bug end to end: a daily scheduled trigger that gets skipped for
+// max_concurrent_runs must not be considered due again on the scheduler's
+// next check tick (30s later in production). Before the fix, a stale
+// LastEvaluatedAt made shouldFire return true on every tick, spamming a new
+// "max_concurrent_runs=n reached" skipped run roughly once a minute forever.
+func TestCronScheduler_DailyTrigger_DoesNotRefireNextTick(t *testing.T) {
+	svc := newTestService(t)
+	ctx := context.Background()
+	log, _ := logger.NewFromZap(zap.NewNop())
+	cs := NewCronScheduler(svc, log)
+
+	a := &Automation{
+		WorkspaceID:       "ws-1",
+		Name:              "Daily rebase",
+		WorkflowID:        "wf-1",
+		WorkflowStepID:    "s-1",
+		Enabled:           true,
+		MaxConcurrentRuns: 1,
+	}
+	if err := svc.store.CreateAutomation(ctx, a); err != nil {
+		t.Fatal(err)
+	}
+
+	cfg, _ := json.Marshal(ScheduledTriggerConfig{CronExpression: "@daily"})
+	trig := &AutomationTrigger{AutomationID: a.ID, Type: TriggerTypeScheduled, Config: cfg, Enabled: true}
+	if err := svc.store.CreateTrigger(ctx, trig); err != nil {
+		t.Fatal(err)
+	}
+
+	active := &AutomationRun{
+		AutomationID: a.ID,
+		TriggerID:    trig.ID,
+		TriggerType:  TriggerTypeScheduled,
+		Status:       RunStatusTaskCreated,
+		DedupKey:     "seed-active-run",
+		TriggerData:  json.RawMessage(`{}`),
+	}
+	if err := svc.store.CreateRun(ctx, active); err != nil {
+		t.Fatal(err)
+	}
+
+	now := time.Now()
+	cs.fire(ctx, trig, now)
+
+	triggers, err := svc.store.ListTriggers(ctx, a.ID)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if len(triggers) != 1 {
+		t.Fatalf("expected 1 trigger, got %d", len(triggers))
+	}
+	updated := triggers[0]
+
+	// One minute later — well within the @daily interval — the scheduler
+	// must not treat the trigger as due again.
+	if cs.shouldFire(&updated, now.Add(time.Minute)) {
+		t.Fatal("expected shouldFire to be false one minute after a skipped evaluation of a daily trigger")
+	}
+}
+
+// TestFireTrigger_ConcurrencyCapCheckError_DoesNotAdvanceLastEvaluatedAt guards
+// against silently missing a whole day of a @daily trigger's schedule. If
+// maybeSkipForConcurrencyCap fails for an infrastructural reason (e.g. the
+// reader pool backing CountActiveRuns is briefly unavailable), FireTrigger
+// must return the error without having already advanced LastEvaluatedAt.
+// Otherwise CronScheduler.shouldFire treats the trigger as freshly
+// evaluated and suppresses the next attempt until the full cron interval
+// elapses, instead of retrying on the next 30s scheduler tick.
+func TestFireTrigger_ConcurrencyCapCheckError_DoesNotAdvanceLastEvaluatedAt(t *testing.T) {
+	svc := newTestService(t)
+	ctx := context.Background()
+
+	a := &Automation{
+		WorkspaceID:       "ws-1",
+		Name:              "Daily rebase",
+		WorkflowID:        "wf-1",
+		WorkflowStepID:    "s-1",
+		Enabled:           true,
+		MaxConcurrentRuns: 1,
+	}
+	if err := svc.store.CreateAutomation(ctx, a); err != nil {
+		t.Fatal(err)
+	}
+
+	cfg, _ := json.Marshal(ScheduledTriggerConfig{CronExpression: "@daily"})
+	trig := &AutomationTrigger{AutomationID: a.ID, Type: TriggerTypeScheduled, Config: cfg, Enabled: true}
+	if err := svc.store.CreateTrigger(ctx, trig); err != nil {
+		t.Fatal(err)
+	}
+
+	// Break CountActiveRuns in isolation: it queries automation_runs while
+	// GetAutomation (the earlier lookup in maybeSkipForConcurrencyCap) only
+	// queries automations, so dropping just the former reproduces "the cap
+	// check itself failed" without masking the failure behind an earlier,
+	// softly-handled lookup error.
+	if _, err := svc.store.db.ExecContext(ctx, `DROP TABLE automation_runs`); err != nil {
+		t.Fatal(err)
+	}
+
+	if err := svc.FireTrigger(ctx, a.ID, trig.ID, TriggerTypeScheduled, json.RawMessage(`{}`), ""); err == nil {
+		t.Fatal("expected FireTrigger to return the concurrency-cap check error")
+	}
+
+	triggers, err := svc.store.ListTriggers(ctx, a.ID)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if len(triggers) != 1 {
+		t.Fatalf("expected 1 trigger, got %d", len(triggers))
+	}
+	if triggers[0].LastEvaluatedAt != nil {
+		t.Fatal("expected LastEvaluatedAt to remain nil after a concurrency-cap check error, got non-nil")
+	}
+}
diff --git a/apps/backend/internal/automation/service.go b/apps/backend/internal/automation/service.go
index 96d8002456..be76abbedd 100644
--- a/apps/backend/internal/automation/service.go
+++ b/apps/backend/internal/automation/service.go
@@ -200,6 +200,23 @@ func (s *Service) FireTrigger(ctx context.Context, automationID, triggerID strin
 	if capErr != nil {
 		return capErr
 	}
+
+	// Record that the trigger was evaluated now that the cap check itself
+	// has succeeded. Scheduled triggers use this to pace themselves against
+	// their cron interval (CronScheduler.shouldFire): if this were updated
+	// before the cap check (or despite the cap check returning an error), an
+	// infrastructural failure in the check would look like a completed
+	// evaluation and suppress the next attempt until the full cron interval
+	// elapses, instead of retrying on the next scheduler tick. And if it
+	// were only updated on an actual fire, a trigger stuck behind
+	// max_concurrent_runs would look "overdue" again on every subsequent
+	// tick and get re-evaluated — and re-skipped — far more often than its
+	// configured schedule.
+	now := time.Now().UTC()
+	if updateErr := s.store.UpdateTriggerEvaluatedAt(ctx, triggerID, now); updateErr != nil {
+		s.logger.Warn("failed to update last_evaluated_at",
+			zap.String("trigger_id", triggerID), zap.Error(updateErr))
+	}
 	if skipped {
 		return nil
 	}
@@ -212,15 +229,10 @@ func (s *Service) FireTrigger(ctx context.Context, automationID, triggerID strin
 		DedupKey:     dedupKey,
 	}
 
-	now := time.Now().UTC()
 	if updateErr := s.store.UpdateLastTriggered(ctx, automationID, now); updateErr != nil {
 		s.logger.Warn("failed to update last_triggered_at",
 			zap.String("automation_id", automationID), zap.Error(updateErr))
 	}
-	if updateErr := s.store.UpdateTriggerEvaluatedAt(ctx, triggerID, now); updateErr != nil {
-		s.logger.Warn("failed to update last_evaluated_at",
-			zap.String("trigger_id", triggerID), zap.Error(updateErr))
-	}
 
 	event := bus.NewEvent(events.AutomationTriggered, "automation_service", evt)
 	if err := s.eventBus.Publish(ctx, events.AutomationTriggered, event); err != nil {