diff --git a/internal/cluster/orchestrator_service_stability.go b/internal/cluster/orchestrator_service_stability.go
index cc5d017..9102d9d 100644
--- a/internal/cluster/orchestrator_service_stability.go
+++ b/internal/cluster/orchestrator_service_stability.go
@@ -341,8 +341,14 @@ func (o *Orchestrator) waitForStabilityWindow(ctx context.Context) error {
 	if poll <= 0 {
 		poll = 5 * time.Second
 	}
-	deadline := time.Now().Add(window)
+	maxWait := window * 3
+	if maxWait < window+poll {
+		maxWait = window + poll
+	}
+	deadline := time.Now().Add(maxWait)
+	stableSince := time.Time{}
 	lastStatus := time.Time{}
+	lastFailure := ""
 	lastRecycleAttempt := time.Time{}
 	lastReplicaHeal := time.Time{}
 
@@ -350,19 +356,36 @@ func (o *Orchestrator) waitForStabilityWindow(ctx context.Context) error {
 		o.maybeAutoRecycleStuckPods(ctx, &lastRecycleAttempt)
 		o.maybeAutoHealCriticalWorkloadReplicas(ctx, &lastReplicaHeal)
 		if err := o.startupStabilityHealthy(ctx); err != nil {
-			return fmt.Errorf("startup stability window failed: %w", err)
-		}
-		if time.Now().After(deadline) {
-			o.log.Printf("startup stability window passed (%s)", window)
-			return nil
-		}
-		if time.Since(lastStatus) >= 30*time.Second {
-			remaining := time.Until(deadline).Round(time.Second)
-			if remaining < 0 {
-				remaining = 0
+			lastFailure = err.Error()
+			stableSince = time.Time{}
+			if time.Now().After(deadline) {
+				return fmt.Errorf("startup stability window failed after %s: %s", maxWait, lastFailure)
+			}
+			if time.Since(lastStatus) >= 30*time.Second {
+				remaining := time.Until(deadline).Round(time.Second)
+				if remaining < 0 {
+					remaining = 0
+				}
+				o.log.Printf("startup stability soak reset (%s remaining): %s", remaining, lastFailure)
+				lastStatus = time.Now()
+			}
+		} else {
+			if stableSince.IsZero() {
+				stableSince = time.Now()
+			}
+			stableFor := time.Since(stableSince)
+			if stableFor >= window {
+				o.log.Printf("startup stability window passed (%s)", window)
+				return nil
+			}
+			if time.Since(lastStatus) >= 30*time.Second {
+				remaining := (window - stableFor).Round(time.Second)
+				if remaining < 0 {
+					remaining = 0
+				}
+				o.log.Printf("startup stability soak in progress (%s remaining)", remaining)
+				lastStatus = time.Now()
 			}
-			o.log.Printf("startup stability soak in progress (%s remaining)", remaining)
-			lastStatus = time.Now()
 		}
 		select {
 		case <-ctx.Done():