diff --git a/Makefile b/Makefile
index 33dab1655..658928eb1 100644
--- a/Makefile
+++ b/Makefile
@@ -97,7 +97,7 @@ e2e: deepcopy-gen manifests ## Runs e2e tests, you can use EXTRA_ARGS
 .PHONY: helm-e2e
 IMAGE_NAME := $(DOCKER_REGISTRY):$(GITCOMMIT)
 #TODO: install cert-manager before running helm charts
-helm-e2e:  helm install-cert-manager container-runtime-build ## Runs helm e2e tests, you can use EXTRA_ARGS
+helm-e2e:  helm container-runtime-build ## Runs helm e2e tests, you can use EXTRA_ARGS
 	@echo "+ $@"
 	RUNNING_TESTS=1 go test -parallel=1 "./test/helm/" -ginkgo.v -tags "$(BUILDTAGS) cgo" -v -timeout 60m -run "$(E2E_TEST_SELECTOR)" -image-name=$(IMAGE_NAME) $(E2E_TEST_ARGS)
 
@@ -538,8 +538,10 @@ all-in-one-build-webhook: ## Re-generate all-in-one yaml
 	
 # start the cluster locally and set it to use the docker daemon from minikube
 install-cert-manager: minikube-start
-	kubectl apply -f https://github.com/jetstack/cert-manager/releases/download/v1.4.0/cert-manager.yaml 
+	kubectl apply -f https://github.com/jetstack/cert-manager/releases/download/v1.5.1/cert-manager.yaml 
 
+uninstall-cert-manager: minikube-start
+	kubectl delete -f https://github.com/jetstack/cert-manager/releases/download/v1.5.1/cert-manager.yaml 
 	
 #Launch cert-manager and deploy the operator locally along with webhook
 deploy-webhook: install-cert-manager install-crds container-runtime-build all-in-one-build-webhook 
diff --git a/api/v1alpha2/jenkins_webhook.go b/api/v1alpha2/jenkins_webhook.go
index 1fe68a5db..8d340b464 100644
--- a/api/v1alpha2/jenkins_webhook.go
+++ b/api/v1alpha2/jenkins_webhook.go
@@ -26,6 +26,7 @@ import (
 	"os"
 	"time"
 
+	//"github.com/jenkinsci/kubernetes-operator/pkg/configuration/base/resources"
 	"github.com/jenkinsci/kubernetes-operator/pkg/constants"
 	"github.com/jenkinsci/kubernetes-operator/pkg/plugins"
 
@@ -345,15 +346,32 @@ func CreateJenkinsCR(name string, namespace string, userPlugins []Plugin, valida
 			Namespace: namespace,
 		},
 		Spec: JenkinsSpec{
+			GroovyScripts: GroovyScripts{
+				Customization: Customization{
+					Configurations: []ConfigMapRef{},
+					Secret: SecretRef{
+						Name: "",
+					},
+				},
+			},
+			ConfigurationAsCode: ConfigurationAsCode{
+				Customization: Customization{
+					Configurations: []ConfigMapRef{},
+					Secret: SecretRef{
+						Name: "",
+					},
+				},
+			},
 			Master: JenkinsMaster{
-				Annotations: map[string]string{"test": "label"},
-				Plugins:     userPlugins,
+				Plugins:               userPlugins,
+				DisableCSRFProtection: false,
 			},
 			ValidateSecurityWarnings: validateSecurityWarnings,
 			Service: Service{
 				Type: corev1.ServiceTypeNodePort,
 				Port: constants.DefaultHTTPPortInt32,
 			},
+			JenkinsAPISettings: JenkinsAPISettings{AuthorizationStrategy: CreateUserAuthorizationStrategy},
 		},
 	}
 
diff --git a/chart/jenkins-operator/templates/jenkins.yaml b/chart/jenkins-operator/templates/jenkins.yaml
index 9ba138b0f..aae8f6acd 100644
--- a/chart/jenkins-operator/templates/jenkins.yaml
+++ b/chart/jenkins-operator/templates/jenkins.yaml
@@ -145,8 +145,8 @@ spec:
     securityContext:
     {{- toYaml . | nindent 6 }}
     {{- end }}
-  {{- with .Values.jenkins.seedJobs }}
   ValidateSecurityWarnings: {{ .Values.jenkins.ValidateSecurityWarnings }}
+  {{- with .Values.jenkins.seedJobs }}
   seedJobs: {{- toYaml . | nindent 4 }}
   {{- end }}
 {{- end }}
diff --git a/chart/jenkins-operator/templates/webhook-certificates.yaml b/chart/jenkins-operator/templates/webhook-certificates.yaml
index 3edc1045c..cb87becf7 100644
--- a/chart/jenkins-operator/templates/webhook-certificates.yaml
+++ b/chart/jenkins-operator/templates/webhook-certificates.yaml
@@ -25,4 +25,10 @@ spec:
   selfSigned: {}
 
 ---
+apiVersion: v1
+kind: Secret
+metadata:
+  name: jenkins-{{ .Values.webhook.certificate.name }}
+type: opaque
+
 {{- end }}
\ No newline at end of file
diff --git a/chart/jenkins-operator/templates/webhook.yaml b/chart/jenkins-operator/templates/webhook.yaml
index 69f07693c..bf31ce5e4 100644
--- a/chart/jenkins-operator/templates/webhook.yaml
+++ b/chart/jenkins-operator/templates/webhook.yaml
@@ -16,6 +16,7 @@ webhooks:
       path: /validate-jenkins-io-v1alpha2-jenkins
   failurePolicy: Fail
   name: vjenkins.kb.io
+  timeoutSeconds: 30
   rules:
   - apiGroups:
     - jenkins.io
diff --git a/chart/jenkins-operator/values.yaml b/chart/jenkins-operator/values.yaml
index 531a3098a..ce3fb1c8f 100644
--- a/chart/jenkins-operator/values.yaml
+++ b/chart/jenkins-operator/values.yaml
@@ -292,4 +292,10 @@ webhook:
     # time after which the certificate will be automatically renewed 
     renewbefore: 360h
   # enable or disable the validation webhook
-  enabled: false
\ No newline at end of file
+  enabled: false
+
+# This startupapicheck is a Helm post-install hook that waits for the webhook
+# endpoints to become available.
+cert-manager:
+  startupapicheck:
+    enabled: false
\ No newline at end of file
diff --git a/config/crd/bases/jenkins.io_jenkins.yaml b/config/crd/bases/jenkins.io_jenkins.yaml
index 47d626c6e..953509023 100644
--- a/config/crd/bases/jenkins.io_jenkins.yaml
+++ b/config/crd/bases/jenkins.io_jenkins.yaml
@@ -5,6 +5,7 @@ kind: CustomResourceDefinition
 metadata:
   annotations:
     controller-gen.kubebuilder.io/version: v0.4.1
+  creationTimestamp: null
   name: jenkins.jenkins.io
 spec:
   group: jenkins.io
diff --git a/main.go b/main.go
index 543edad1e..8a6fe1ba4 100644
--- a/main.go
+++ b/main.go
@@ -180,8 +180,10 @@ func main() {
 		fatal(errors.Wrap(err, "unable to create Jenkins controller"), *debug)
 	}
 
-	if err = (&v1alpha2.Jenkins{}).SetupWebhookWithManager(mgr); err != nil {
-		fatal(errors.Wrap(err, "unable to create Webhook"), *debug)
+	if ValidateSecurityWarnings {
+		if err = (&v1alpha2.Jenkins{}).SetupWebhookWithManager(mgr); err != nil {
+			fatal(errors.Wrap(err, "unable to create Webhook"), *debug)
+		}
 	}
 	// +kubebuilder:scaffold:builder
 
diff --git a/test/helm/helm_test.go b/test/helm/helm_test.go
index bc05172a9..cfdb35ab1 100644
--- a/test/helm/helm_test.go
+++ b/test/helm/helm_test.go
@@ -1,20 +1,26 @@
 package helm
 
 import (
+	"context"
 	"fmt"
 	"os/exec"
+	"time"
 
 	"github.com/jenkinsci/kubernetes-operator/api/v1alpha2"
+	"github.com/jenkinsci/kubernetes-operator/pkg/configuration/base/resources"
+	"github.com/jenkinsci/kubernetes-operator/pkg/constants"
 	"github.com/jenkinsci/kubernetes-operator/test/e2e"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+	"k8s.io/apimachinery/pkg/util/intstr"
 
 	. "github.com/onsi/ginkgo"
 	. "github.com/onsi/gomega"
 	corev1 "k8s.io/api/core/v1"
-	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	// +kubebuilder:scaffold:imports
 )
 
-var _ = Describe("Jenkins controller", func() {
+var _ = Describe("Jenkins Controller with webhook", func() {
+
 	var (
 		namespace *corev1.Namespace
 	)
@@ -23,38 +29,193 @@ var _ = Describe("Jenkins controller", func() {
 		namespace = e2e.CreateNamespace()
 	})
 	AfterEach(func() {
+		cmd := exec.Command("../../bin/helm", "delete", "jenkins", "--namespace", namespace.Name)
+		output, err := cmd.CombinedOutput()
+		Expect(err).NotTo(HaveOccurred(), string(output))
+
 		e2e.ShowLogsIfTestHasFailed(CurrentGinkgoTestDescription().Failed, namespace.Name)
 		e2e.DestroyNamespace(namespace)
 	})
-	Context("when deploying Helm Chart to cluster", func() {
-		It("creates Jenkins instance and configures it", func() {
-
-			jenkins := &v1alpha2.Jenkins{
-				TypeMeta: v1alpha2.JenkinsTypeMeta(),
-				ObjectMeta: metav1.ObjectMeta{
-					Name:      "jenkins",
-					Namespace: namespace.Name,
-				},
-			}
+	It("Deploys Jenkins operator with webhook enabled along with the default jenkins image", func() {
+		jenkins := &v1alpha2.Jenkins{
+			TypeMeta: v1alpha2.JenkinsTypeMeta(),
+			ObjectMeta: metav1.ObjectMeta{
+				Name:      "jenkins",
+				Namespace: namespace.Name,
+			},
+		}
+
+		cmd := exec.Command("../../bin/helm", "upgrade", "jenkins", "../../chart/jenkins-operator", "--namespace", namespace.Name, "--debug",
+			"--set-string", fmt.Sprintf("jenkins.namespace=%s", namespace.Name),
+			"--set-string", fmt.Sprintf("operator.image=%s", *imageName), "--install", "--wait")
+		output, err := cmd.CombinedOutput()
+		Expect(err).NotTo(HaveOccurred(), string(output))
+
+		e2e.WaitForJenkinsBaseConfigurationToComplete(jenkins)
+		e2e.WaitForJenkinsUserConfigurationToComplete(jenkins)
+
+	})
 
-			cmd := exec.Command("../../bin/helm", "upgrade", "jenkins", "../../chart/jenkins-operator", "--namespace", namespace.Name, "--debug",
-				"--set-string", fmt.Sprintf("jenkins.namespace=%s", namespace.Name),
-				"--set-string", fmt.Sprintf("operator.image=%s", *imageName), "--install")
-			output, err := cmd.CombinedOutput()
-			Expect(err).NotTo(HaveOccurred(), string(output))
+	It("Deploys Jenkins operator along with webhook and cert-manager", func() {
 
-			e2e.WaitForJenkinsBaseConfigurationToComplete(jenkins)
-			e2e.WaitForJenkinsUserConfigurationToComplete(jenkins)
+		By("Deploying the operator along with webhook and cert-manager")
+		cmd := exec.Command("../../bin/helm", "upgrade", "jenkins", "../../chart/jenkins-operator", "--namespace", namespace.Name, "--debug",
+			"--set-string", fmt.Sprintf("jenkins.namespace=%s", namespace.Name), "--set-string", fmt.Sprintf("operator.image=%s", *imageName),
+			"--set", fmt.Sprintf("webhook.enabled=%t", true), "--set", fmt.Sprintf("jenkins.enabled=%t", false), "--install", "--wait")
+		output, err := cmd.CombinedOutput()
+		Expect(err).NotTo(HaveOccurred(), string(output))
 
-			cmd = exec.Command("../../bin/helm", "upgrade", "jenkins", "../../chart/jenkins-operator", "--namespace", namespace.Name, "--debug",
-				"--set-string", fmt.Sprintf("jenkins.namespace=%s", namespace.Name),
-				"--set-string", fmt.Sprintf("operator.image=%s", *imageName), "--install")
-			output, err = cmd.CombinedOutput()
+		By("Waiting for the operator to fetch the plugin data ")
+		time.Sleep(time.Duration(200) * time.Second)
 
-			Expect(err).NotTo(HaveOccurred(), string(output))
+		By("Denies a create request for a Jenkins custom resource with some plugins having security warnings and validation is turned on")
+		userplugins := []v1alpha2.Plugin{
+			{Name: "simple-theme-plugin", Version: "0.6"},
+			{Name: "audit-trail", Version: "3.5"},
+			{Name: "github", Version: "1.29.0"},
+		}
+		jenkins := CreateJenkinsCR("jenkins", namespace.Name, userplugins, true)
+		Expect(e2e.K8sClient.Create(context.TODO(), jenkins)).Should(MatchError("admission webhook \"vjenkins.kb.io\" denied the request: security vulnerabilities detected in the following user-defined plugins: \naudit-trail:3.5\ngithub:1.29.0"))
 
-			e2e.WaitForJenkinsBaseConfigurationToComplete(jenkins)
-			e2e.WaitForJenkinsUserConfigurationToComplete(jenkins)
-		})
+		By("Creating the same Jenkins custom resource with some plugins having security warnings but validation is turned off")
+		userplugins = []v1alpha2.Plugin{
+			{Name: "simple-theme-plugin", Version: "0.6"},
+			{Name: "audit-trail", Version: "3.5"},
+			{Name: "github", Version: "1.31.0"},
+		}
+		jenkins = CreateJenkinsCR("jenkins", namespace.Name, userplugins, false)
+		Expect(e2e.K8sClient.Create(context.TODO(), jenkins)).Should(Succeed())
+		e2e.WaitForJenkinsBaseConfigurationToComplete(jenkins)
+		e2e.WaitForJenkinsUserConfigurationToComplete(jenkins)
+
+		By("Updating the Jenkins resource with plugins not having any security warnings and validation is turned on")
+		userplugins = []v1alpha2.Plugin{
+			{Name: "simple-theme-plugin", Version: "0.6"},
+			{Name: "audit-trail", Version: "3.8"},
+			{Name: "github", Version: "2.9"},
+		}
+		jenkins.Spec.Master.Plugins = userplugins
+		jenkins.Spec.ValidateSecurityWarnings = true
+		Expect(e2e.K8sClient.Update(context.TODO(), jenkins)).Should(Succeed())
+		jenkins = &v1alpha2.Jenkins{
+			TypeMeta: v1alpha2.JenkinsTypeMeta(),
+			ObjectMeta: metav1.ObjectMeta{
+				Name:      "jenkins",
+				Namespace: namespace.Name,
+			},
+		}
+		e2e.WaitForJenkinsBaseConfigurationToComplete(jenkins)
+		e2e.WaitForJenkinsUserConfigurationToComplete(jenkins)
+
+		By("Failing to update the Jenkins custom resource because some plugins having security warnings and validation is turned on")
+		userplugins = []v1alpha2.Plugin{
+			{Name: "vncviewer", Version: "1.7"},
+			{Name: "build-timestamp", Version: "1.0.3"},
+			{Name: "deployit-plugin", Version: "7.5.5"},
+			{Name: "github-branch-source", Version: "2.0.7"},
+			{Name: "aws-lambda-cloud", Version: "0.4"},
+			{Name: "groovy", Version: "1.31"},
+			{Name: "google-login", Version: "1.2"},
+		}
+		jenkins.Spec.Master.Plugins = userplugins
+		Expect(e2e.K8sClient.Update(context.TODO(), jenkins)).Should(MatchError("admission webhook \"vjenkins.kb.io\" denied the request: security vulnerabilities detected in the following user-defined plugins: \nvncviewer:1.7\ndeployit-plugin:7.5.5\ngithub-branch-source:2.0.7\ngroovy:1.31\ngoogle-login:1.2"))
 	})
 })
+
+func CreateJenkinsCR(name string, namespace string, userPlugins []v1alpha2.Plugin, validateSecurityWarnings bool) *v1alpha2.Jenkins {
+	jenkins := &v1alpha2.Jenkins{
+		TypeMeta: v1alpha2.JenkinsTypeMeta(),
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      name,
+			Namespace: namespace,
+		},
+		Spec: v1alpha2.JenkinsSpec{
+			GroovyScripts: v1alpha2.GroovyScripts{
+				Customization: v1alpha2.Customization{
+					Configurations: []v1alpha2.ConfigMapRef{},
+					Secret: v1alpha2.SecretRef{
+						Name: "",
+					},
+				},
+			},
+			ConfigurationAsCode: v1alpha2.ConfigurationAsCode{
+				Customization: v1alpha2.Customization{
+					Configurations: []v1alpha2.ConfigMapRef{},
+					Secret: v1alpha2.SecretRef{
+						Name: "",
+					},
+				},
+			},
+			Master: v1alpha2.JenkinsMaster{
+				Containers: []v1alpha2.Container{
+					{
+						Name: resources.JenkinsMasterContainerName,
+						Env: []corev1.EnvVar{
+							{
+								Name:  "TEST_ENV",
+								Value: "test_env_value",
+							},
+						},
+						ReadinessProbe: &corev1.Probe{
+							Handler: corev1.Handler{
+								HTTPGet: &corev1.HTTPGetAction{
+									Path:   "/login",
+									Port:   intstr.FromString("http"),
+									Scheme: corev1.URISchemeHTTP,
+								},
+							},
+							InitialDelaySeconds: int32(100),
+							TimeoutSeconds:      int32(4),
+							FailureThreshold:    int32(40),
+							SuccessThreshold:    int32(1),
+							PeriodSeconds:       int32(10),
+						},
+						LivenessProbe: &corev1.Probe{
+							Handler: corev1.Handler{
+								HTTPGet: &corev1.HTTPGetAction{
+									Path:   "/login",
+									Port:   intstr.FromString("http"),
+									Scheme: corev1.URISchemeHTTP,
+								},
+							},
+							InitialDelaySeconds: int32(80),
+							TimeoutSeconds:      int32(4),
+							FailureThreshold:    int32(30),
+							SuccessThreshold:    int32(1),
+							PeriodSeconds:       int32(5),
+						},
+						VolumeMounts: []corev1.VolumeMount{
+							{
+								Name:      "plugins-cache",
+								MountPath: "/usr/share/jenkins/ref/plugins",
+							},
+						},
+					},
+					{
+						Name:  "envoyproxy",
+						Image: "envoyproxy/envoy-alpine:v1.14.1",
+					},
+				},
+				Plugins:               userPlugins,
+				DisableCSRFProtection: false,
+				NodeSelector:          map[string]string{"kubernetes.io/os": "linux"},
+				Volumes: []corev1.Volume{
+					{
+						Name: "plugins-cache",
+						VolumeSource: corev1.VolumeSource{
+							EmptyDir: &corev1.EmptyDirVolumeSource{},
+						},
+					},
+				},
+			},
+			ValidateSecurityWarnings: validateSecurityWarnings,
+			Service: v1alpha2.Service{
+				Type: corev1.ServiceTypeNodePort,
+				Port: constants.DefaultHTTPPortInt32,
+			},
+			JenkinsAPISettings: v1alpha2.JenkinsAPISettings{AuthorizationStrategy: v1alpha2.CreateUserAuthorizationStrategy},
+		},
+	}
+
+	return jenkins
+}