diff --git a/api/v1beta1/kustomization_types.go b/api/v1beta1/kustomization_types.go
index 6710dfbd..4d955ee7 100644
--- a/api/v1beta1/kustomization_types.go
+++ b/api/v1beta1/kustomization_types.go
@@ -30,7 +30,7 @@ import (
 const (
 	KustomizationKind         = "Kustomization"
 	KustomizationFinalizer    = "finalizers.fluxcd.io"
-	MaxConditionMessageLength = 4000
+	MaxConditionMessageLength = 20000
 )
 
 // KustomizationSpec defines the desired state of a kustomization.
@@ -181,14 +181,14 @@ func KustomizationProgressing(k Kustomization) Kustomization {
 // SetKustomizeReadiness sets the ReadyCondition, ObservedGeneration, and LastAttemptedRevision,
 // on the Kustomization.
 func SetKustomizationReadiness(k *Kustomization, status metav1.ConditionStatus, reason, message string, revision string) {
-	meta.SetResourceCondition(k, meta.ReadyCondition, status, reason, message)
+	meta.SetResourceCondition(k, meta.ReadyCondition, status, reason, trimString(message, MaxConditionMessageLength))
 	k.Status.ObservedGeneration = k.Generation
 	k.Status.LastAttemptedRevision = revision
 }
 
 // KustomizationNotReady registers a failed apply attempt of the given Kustomization.
 func KustomizationNotReady(k Kustomization, revision, reason, message string) Kustomization {
-	SetKustomizationReadiness(&k, metav1.ConditionFalse, reason, message, revision)
+	SetKustomizationReadiness(&k, metav1.ConditionFalse, reason, trimString(message, MaxConditionMessageLength), revision)
 	if revision != "" {
 		k.Status.LastAttemptedRevision = revision
 	}
@@ -198,7 +198,7 @@ func KustomizationNotReady(k Kustomization, revision, reason, message string) Ku
 // KustomizationNotReady registers a failed apply attempt of the given Kustomization,
 // including a Snapshot.
 func KustomizationNotReadySnapshot(k Kustomization, snapshot *Snapshot, revision, reason, message string) Kustomization {
-	SetKustomizationReadiness(&k, metav1.ConditionFalse, reason, message, revision)
+	SetKustomizationReadiness(&k, metav1.ConditionFalse, reason, trimString(message, MaxConditionMessageLength), revision)
 	k.Status.Snapshot = snapshot
 	k.Status.LastAttemptedRevision = revision
 	return k
@@ -206,7 +206,7 @@ func KustomizationNotReadySnapshot(k Kustomization, snapshot *Snapshot, revision
 
 // KustomizationReady registers a successful apply attempt of the given Kustomization.
 func KustomizationReady(k Kustomization, snapshot *Snapshot, revision, reason, message string) Kustomization {
-	SetKustomizationReadiness(&k, metav1.ConditionTrue, reason, message, revision)
+	SetKustomizationReadiness(&k, metav1.ConditionTrue, reason, trimString(message, MaxConditionMessageLength), revision)
 	k.Status.Snapshot = snapshot
 	k.Status.LastAppliedRevision = revision
 	return k
diff --git a/controllers/kustomization_controller.go b/controllers/kustomization_controller.go
index 05ce4ff7..a2c4ad05 100644
--- a/controllers/kustomization_controller.go
+++ b/controllers/kustomization_controller.go
@@ -711,10 +711,15 @@ func (r *KustomizationReconciler) apply(kustomization kustomizev1.Kustomization,
 		if errors.Is(err, context.DeadlineExceeded) {
 			return "", fmt.Errorf("apply timeout: %w", err)
 		}
-		return "", fmt.Errorf("apply failed: %s", string(output))
+
+		if string(output) == "" {
+			return "", fmt.Errorf("apply failed: %w, kubectl process was killed, probably due to OOM", err)
+		}
+
+		return "", fmt.Errorf("apply failed: %s", parseApplyError(output))
 	}
 
-	resources := r.parseApplyOutput(output)
+	resources := parseApplyOutput(output)
 	r.Log.WithValues(
 		strings.ToLower(kustomization.Kind),
 		fmt.Sprintf("%s/%s", kustomization.GetNamespace(), kustomization.GetName()),
@@ -805,27 +810,6 @@ func (r *KustomizationReconciler) checkHealth(statusPoller *polling.StatusPoller
 	return nil
 }
 
-func (r *KustomizationReconciler) parseApplyOutput(in []byte) map[string]string {
-	result := make(map[string]string)
-	input := strings.Split(string(in), "\n")
-	if len(input) == 0 {
-		return result
-	}
-	var parts []string
-	for _, str := range input {
-		if str != "" {
-			parts = append(parts, str)
-		}
-	}
-	for _, str := range parts {
-		kv := strings.Split(str, " ")
-		if len(kv) > 1 {
-			result[kv[0]] = kv[1]
-		}
-	}
-	return result
-}
-
 func (r *KustomizationReconciler) checkDependencies(kustomization kustomizev1.Kustomization) error {
 	for _, d := range kustomization.Spec.DependsOn {
 		if d.Namespace == "" {
@@ -1041,12 +1025,3 @@ func (r *KustomizationReconciler) updateStatus(ctx context.Context, req ctrl.Req
 
 	return r.Status().Patch(ctx, &kustomization, patch)
 }
-
-func containsString(slice []string, s string) bool {
-	for _, item := range slice {
-		if item == s {
-			return true
-		}
-	}
-	return false
-}
diff --git a/controllers/utils.go b/controllers/utils.go
new file mode 100644
index 00000000..fbcac1f2
--- /dev/null
+++ b/controllers/utils.go
@@ -0,0 +1,71 @@
+/*
+Copyright 2020 The Flux authors
+
+Licensed under the Apache License, Version 2.0 (the "License");
+you may not use this file except in compliance with the License.
+You may obtain a copy of the License at
+
+    http://www.apache.org/licenses/LICENSE-2.0
+
+Unless required by applicable law or agreed to in writing, software
+distributed under the License is distributed on an "AS IS" BASIS,
+WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+See the License for the specific language governing permissions and
+limitations under the License.
+*/
+
+package controllers
+
+import "strings"
+
+// parseApplyOutput extracts the objects and the action
+// performed by kubectl e.g.:
+// service/backend created
+// service/frontend configured
+// service/database unchanged
+func parseApplyOutput(in []byte) map[string]string {
+	result := make(map[string]string)
+	input := strings.Split(string(in), "\n")
+	if len(input) == 0 {
+		return result
+	}
+	var parts []string
+	for _, str := range input {
+		if str != "" {
+			parts = append(parts, str)
+		}
+	}
+	for _, str := range parts {
+		kv := strings.Split(str, " ")
+		if len(kv) > 1 {
+			result[kv[0]] = kv[1]
+		}
+	}
+	return result
+}
+
+// parseApplyError extracts the errors from the kubectl
+// apply output by removing the successfully applied objects
+func parseApplyError(in []byte) string {
+	errors := ""
+	lines := strings.Split(string(in), "\n")
+	for _, line := range lines {
+		if line != "" &&
+			!strings.HasSuffix(line, "created") &&
+			!strings.HasSuffix(line, "configured") &&
+			!strings.HasSuffix(line, "unchanged") {
+			errors += line + "\n"
+		}
+	}
+
+	return errors
+}
+
+func containsString(slice []string, s string) bool {
+	for _, item := range slice {
+		if item == s {
+			return true
+		}
+	}
+	return false
+}