diff --git a/pkg/engine/mutate/strategicPreprocessing.go b/pkg/engine/mutate/strategicPreprocessing.go
index 33e453843d..44a9940449 100644
--- a/pkg/engine/mutate/strategicPreprocessing.go
+++ b/pkg/engine/mutate/strategicPreprocessing.go
@@ -10,12 +10,40 @@ import (
 	yaml "sigs.k8s.io/kustomize/kyaml/yaml"
 )
 
+type ValidationError struct {
+	err error
+}
+
+func (ve ValidationError) Error() string {
+	return ve.err.Error()
+}
+
+func NewValidationError(err error) error {
+	return ValidationError{err}
+}
+
+type KeyNotFoundError struct {
+	key string
+}
+
+func (e KeyNotFoundError) Error() string {
+	return fmt.Sprintf("could not found \"%s\" key in the resource", e.key)
+}
+
+func NewKeyNotFoundError(message string) error {
+	return KeyNotFoundError{message}
+}
+
 type ConditionError struct {
 	errorChain error
 }
 
 func (ce ConditionError) Error() string {
-	return fmt.Sprintf("Condition failed: %s", ce.errorChain.Error())
+	return fmt.Sprintf("condition failed: %s", ce.errorChain.Error())
+}
+
+func (ce ConditionError) Inner() error {
+	return ce.errorChain
 }
 
 func NewConditionError(err error) error {
@@ -27,7 +55,11 @@ type GlobalConditionError struct {
 }
 
 func (ce GlobalConditionError) Error() string {
-	return fmt.Sprintf("Global condition failed: %s", ce.errorChain.Error())
+	return fmt.Sprintf("global condition failed: %s", ce.errorChain.Error())
+}
+
+func (ce GlobalConditionError) Inner() error {
+	return ce.errorChain
 }
 
 func NewGlobalConditionError(err error) error {
@@ -141,7 +173,7 @@ func processListOfMaps(logger logr.Logger, pattern, resource *yaml.RNode) error
 			for _, resourceElement := range resourceElements {
 				err := preProcessRecursive(logger, patternElement, resourceElement)
 				if err != nil {
-					if _, ok := err.(ConditionError); ok {
+					if shouldSkipArrayElement(err) {
 						// Skip element, if condition has failed
 						continue
 					}
@@ -496,14 +528,27 @@ func validateConditionsInternal(logger logr.Logger, pattern, resource *yaml.RNod
 	for _, condition := range conditions {
 		conditionKey := removeAnchor(condition)
 		if resource == nil || resource.Field(conditionKey) == nil {
-			return fmt.Errorf("could not found \"%s\" key in the resource", conditionKey)
+			return NewKeyNotFoundError(conditionKey)
 		}
 
 		err = checkCondition(logger, pattern.Field(condition).Value, resource.Field(conditionKey).Value)
 		if err != nil {
-			return err
+			return NewValidationError(err)
 		}
 	}
 
 	return nil
 }
+
+func shouldSkipArrayElement(err error) bool {
+	globalErr, isGlobal := err.(GlobalConditionError)
+	_, isCondition := err.(ConditionError)
+
+	if isGlobal {
+		if _, ok := globalErr.Inner().(KeyNotFoundError); ok {
+			return true
+		}
+	}
+
+	return isCondition
+}