Merge pull request #119 from 1Password/release/v1.5.0

Release v1.5.0

.VERSION

@@ -1 +1 @@
-1.3.0
+1.5.0

CHANGELOG.md

@@ -12,85 +12,136 @@
 
 ---
 
-[//]: # (START/v1.3.0)
+[//]: # (START/v1.5.0)
+# v1.5.0
+
+## Features
+ * `OnePasswordItem` now contains a `status` which contains the status of creating the kubernetes secret for a OnePasswordItem. {#52}
+
+## Fixes
+ * The operator no longer logs an error about changing the secret type if the secret type is not actually being changed.
+ * Annotations on a deployment are no longer removed when the operator triggers a restart. {#112}
+
+---
+
+[//]: # "START/v1.4.1"
+
+# v1.4.1
+
+## Fixes
+
+- OwnerReferences on secrets are now persisted after an item is updated. {#101}
+- Annotations from a Deployment or OnePasswordItem are no longer applied to Secrets that are created for it. {#102}
+
+---
+
+[//]: # "START/v1.4.0"
+
+# v1.4.0
+
+## Features
+
+- The operator now declares the an OwnerReference for the secrets it manages. This should stop secrets from getting pruned by tools like Argo CD. {#51,#84,#96}
+
+---
+
+[//]: # "START/v1.3.0"
+
 # v1.3.0
 
 ## Features
-  * Added support for loading secrets from files stored in 1Password. {#47}
+
+- Added support for loading secrets from files stored in 1Password. {#47}
 
 ---
 
-[//]: # (START/v1.2.0)
+[//]: # "START/v1.2.0"
+
 # v1.2.0
 
 ## Features
-  * Support secrets provisioned through FromEnv. {#74}
-  * Support configuration of Kubernetes Secret type. {#87}
-  * Improved logging. (#72)
+
+- Support secrets provisioned through FromEnv. {#74}
+- Support configuration of Kubernetes Secret type. {#87}
+- Improved logging. (#72)
+
 ---
 
-[//]: # (START/v1.1.0)
+[//]: # "START/v1.1.0"
+
 # v1.1.0
 
 ## Fixes
- * Fix normalization for keys in a Secret's `data` section to allow upper- and lower-case alphanumeric characters. {#66}
+
+- Fix normalization for keys in a Secret's `data` section to allow upper- and lower-case alphanumeric characters. {#66}
 
 ---
 
-[//]: # (START/v1.0.2)
+[//]: # "START/v1.0.2"
+
 # v1.0.2
 
 ## Fixes
- * Name normalizer added to handle non-conforming item names.
+
+- Name normalizer added to handle non-conforming item names.
 
 ---
 
-[//]: # (START/v1.0.1)
+[//]: # "START/v1.0.1"
+
 # v1.0.1
 
 ## Features
-* This release also contains an arm64 Docker image. {#20}
-* Docker images are also pushed to the :latest and :<major>.<minor> tags.
+
+- This release also contains an arm64 Docker image. {#20}
+- Docker images are also pushed to the :latest and :<major>.<minor> tags.
 
 ---
 
-[//]: # (START/v1.0.0)
+[//]: # "START/v1.0.0"
+
 # v1.0.0
 
 ## Features:
-* Option to automatically deploy 1Password Connect via the operator
-* Ignore restart annotation when looking for 1Password annotations
-* Release Automation
-* Upgrading apiextensions.k8s.io/v1beta apiversion from the operator custom resource
-* Adding configuration for auto rolling restart on deployments
-* Configure Auto Restarts for a OnePasswordItem Custom Resource
-* Update Connect Dependencies to latest
-* Add Github action for building and testing operator
+
+- Option to automatically deploy 1Password Connect via the operator
+- Ignore restart annotation when looking for 1Password annotations
+- Release Automation
+- Upgrading apiextensions.k8s.io/v1beta apiversion from the operator custom resource
+- Adding configuration for auto rolling restart on deployments
+- Configure Auto Restarts for a OnePasswordItem Custom Resource
+- Update Connect Dependencies to latest
+- Add Github action for building and testing operator
+
 ## Fixes:
-* Fix spec field example for OnePasswordItem in readme
-* Casing of annotations are now consistent
+
+- Fix spec field example for OnePasswordItem in readme
+- Casing of annotations are now consistent
 
 ---
 
-[//]: # (START/v0.0.2)
+[//]: # "START/v0.0.2"
+
 # v0.0.2
 
 ## Features:
-* Items can now be accessed by either `vaults/<vault_id>/items/<item_id>` or `vaults/<vault_title>/items/<item_title>`
+
+- Items can now be accessed by either `vaults/<vault_id>/items/<item_id>` or `vaults/<vault_title>/items/<item_title>`
 
 ---
 
-[//]: # (START/v0.0.1)
+[//]: # "START/v0.0.1"
 
 # v0.0.1
 
 Initial 1Password Operator release
 
 ## Features
-* watches for deployment creations with `onepassword` annotations and creates an associated kubernetes secret
-* watches for `onepasswordsecret` crd creations and creates an associated kubernetes secrets
-* watches for changes to 1Password secrets associated with kubernetes secrets and updates the kubernetes secret with changes
-* restart pods when secret has been updated
-* cleanup of kubernetes secrets when deployment or `onepasswordsecret` is deleted
+
+- watches for deployment creations with `onepassword` annotations and creates an associated kubernetes secret
+- watches for `onepasswordsecret` crd creations and creates an associated kubernetes secrets
+- watches for changes to 1Password secrets associated with kubernetes secrets and updates the kubernetes secret with changes
+- restart pods when secret has been updated
+- cleanup of kubernetes secrets when deployment or `onepasswordsecret` is deleted
 
 ---

deploy/crds/onepassword.com_onepassworditems_crd.yaml

@@ -12,8 +12,6 @@ spec:
   scope: Namespaced
   versions:
   - name: v1
-    served: true
-    storage: true
     schema:
       openAPIV3Schema:
         description: OnePasswordItem is the Schema for the onepassworditems API
@@ -38,8 +36,41 @@ spec:
             type: object
           status:
             description: OnePasswordItemStatus defines the observed state of OnePasswordItem
+            properties:
+              conditions:
+                description: 'Important: Run "operator-sdk generate k8s" to regenerate
+                  code after modifying this file Add custom validation using kubebuilder
+                  tags: https://book-v1.book.kubebuilder.io/beyond_basics/generating_crd.html'
+                items:
+                  properties:
+                    lastTransitionTime:
+                      description: Last time the condition transit from one status
+                        to another.
+                      format: date-time
+                      type: string
+                    message:
+                      description: Human-readable message indicating details about
+                        last transition.
+                      type: string
+                    status:
+                      description: Status of the condition, one of True, False, Unknown.
+                      type: string
+                    type:
+                      description: Type of job condition, Completed.
+                      type: string
+                  required:
+                  - status
+                  - type
+                  type: object
+                type: array
+            required:
+            - conditions
             type: object
           type:
             description: 'Kubernetes secret type. More info: https://kubernetes.io/docs/concepts/configuration/secret/#secret-types'
             type: string
         type: object
+    served: true
+    storage: true
+    subresources:
+      status: {}

pkg/apis/onepassword/v1/onepasswordsecret_types.go

@@ -11,11 +11,31 @@ type OnePasswordItemSpec struct {
 	ItemPath string `json:"itemPath,omitempty"`
 }
 
+type OnePasswordItemConditionType string
+
+const (
+	// OnePasswordItemReady means the Kubernetes secret is ready for use.
+	OnePasswordItemReady OnePasswordItemConditionType = "Ready"
+)
+
+type OnePasswordItemCondition struct {
+	// Type of job condition, Completed.
+	Type OnePasswordItemConditionType `json:"type"`
+	// Status of the condition, one of True, False, Unknown.
+	Status metav1.ConditionStatus `json:"status"`
+	// Last time the condition transit from one status to another.
+	// +optional
+	LastTransitionTime metav1.Time `json:"lastTransitionTime,omitempty"`
+	// Human-readable message indicating details about last transition.
+	// +optional
+	Message string `json:"message,omitempty"`
+}
+
 // OnePasswordItemStatus defines the observed state of OnePasswordItem
 type OnePasswordItemStatus struct {
-	// INSERT ADDITIONAL STATUS FIELD - define observed state of cluster
 	// Important: Run "operator-sdk generate k8s" to regenerate code after modifying this file
 	// Add custom validation using kubebuilder tags: https://book-v1.book.kubebuilder.io/beyond_basics/generating_crd.html
+	Conditions []OnePasswordItemCondition `json:"conditions"`
 }
 
 // +k8s:deepcopy-gen:interfaces=k8s.io/apimachinery/pkg/runtime.Object
@@ -26,7 +46,9 @@ type OnePasswordItemStatus struct {
 type OnePasswordItem struct {
 	metav1.TypeMeta   `json:",inline"`
 	metav1.ObjectMeta `json:"metadata,omitempty"`
-	Type              string `json:"type,omitempty"`
+
+	// Kubernetes secret type. More info: https://kubernetes.io/docs/concepts/configuration/secret/#secret-types
+	Type string `json:"type,omitempty"`
 
 	Spec   OnePasswordItemSpec   `json:"spec,omitempty"`
 	Status OnePasswordItemStatus `json:"status,omitempty"`

pkg/apis/onepassword/v1/zz_generated.deepcopy.go

@@ -1,3 +1,4 @@
+//go:build !ignore_autogenerated
 // +build !ignore_autogenerated
 
 // Code generated by operator-sdk. DO NOT EDIT.
@@ -14,7 +15,7 @@ func (in *OnePasswordItem) DeepCopyInto(out *OnePasswordItem) {
 	out.TypeMeta = in.TypeMeta
 	in.ObjectMeta.DeepCopyInto(&out.ObjectMeta)
 	out.Spec = in.Spec
-	out.Status = in.Status
+	in.Status.DeepCopyInto(&out.Status)
 	return
 }
 
@@ -36,6 +37,23 @@ func (in *OnePasswordItem) DeepCopyObject() runtime.Object {
 	return nil
 }
 
+// DeepCopyInto is an autogenerated deepcopy function, copying the receiver, writing into out. in must be non-nil.
+func (in *OnePasswordItemCondition) DeepCopyInto(out *OnePasswordItemCondition) {
+	*out = *in
+	in.LastTransitionTime.DeepCopyInto(&out.LastTransitionTime)
+	return
+}
+
+// DeepCopy is an autogenerated deepcopy function, copying the receiver, creating a new OnePasswordItemCondition.
+func (in *OnePasswordItemCondition) DeepCopy() *OnePasswordItemCondition {
+	if in == nil {
+		return nil
+	}
+	out := new(OnePasswordItemCondition)
+	in.DeepCopyInto(out)
+	return out
+}
+
 // DeepCopyInto is an autogenerated deepcopy function, copying the receiver, writing into out. in must be non-nil.
 func (in *OnePasswordItemList) DeepCopyInto(out *OnePasswordItemList) {
 	*out = *in
@@ -88,6 +106,13 @@ func (in *OnePasswordItemSpec) DeepCopy() *OnePasswordItemSpec {
 // DeepCopyInto is an autogenerated deepcopy function, copying the receiver, writing into out. in must be non-nil.
 func (in *OnePasswordItemStatus) DeepCopyInto(out *OnePasswordItemStatus) {
 	*out = *in
+	if in.Conditions != nil {
+		in, out := &in.Conditions, &out.Conditions
+		*out = make([]OnePasswordItemCondition, len(*in))
+		for i := range *in {
+			(*in)[i].DeepCopyInto(&(*out)[i])
+		}
+	}
 	return
 }
 

pkg/controller/deployment/deployment_controller.go

@@ -14,9 +14,11 @@ import (
 	appsv1 "k8s.io/api/apps/v1"
 	corev1 "k8s.io/api/core/v1"
 	"k8s.io/apimachinery/pkg/api/errors"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/apimachinery/pkg/runtime"
 	ctrl "sigs.k8s.io/controller-runtime"
 	"sigs.k8s.io/controller-runtime/pkg/client"
+	"sigs.k8s.io/controller-runtime/pkg/client/apiutil"
 	"sigs.k8s.io/controller-runtime/pkg/controller"
 	"sigs.k8s.io/controller-runtime/pkg/handler"
 	logf "sigs.k8s.io/controller-runtime/pkg/log"
@@ -114,7 +116,7 @@ func (r *ReconcileDeployment) Reconcile(request reconcile.Request) (reconcile.Re
 			}
 		}
 		// Handles creation or updating secrets for deployment if needed
-		if err := r.HandleApplyingDeployment(deployment.Namespace, annotations, request); err != nil {
+		if err := r.HandleApplyingDeployment(deployment, deployment.Namespace, annotations, request); err != nil {
 			return reconcile.Result{}, err
 		}
 		return reconcile.Result{}, nil
@@ -187,7 +189,7 @@ func (r *ReconcileDeployment) removeOnePasswordFinalizerFromDeployment(deploymen
 	return r.kubeClient.Update(context.Background(), deployment)
 }
 
-func (r *ReconcileDeployment) HandleApplyingDeployment(namespace string, annotations map[string]string, request reconcile.Request) error {
+func (r *ReconcileDeployment) HandleApplyingDeployment(deployment *appsv1.Deployment, namespace string, annotations map[string]string, request reconcile.Request) error {
 	reqLog := log.WithValues("Request.Namespace", request.Namespace, "Request.Name", request.Name)
 
 	secretName := annotations[op.NameAnnotation]
@@ -204,5 +206,17 @@ func (r *ReconcileDeployment) HandleApplyingDeployment(namespace string, annotat
 		return fmt.Errorf("Failed to retrieve item: %v", err)
 	}
 
-	return kubeSecrets.CreateKubernetesSecretFromItem(r.kubeClient, secretName, namespace, item, annotations[op.RestartDeploymentsAnnotation], secretLabels, secretType, annotations)
+	// Create owner reference.
+	gvk, err := apiutil.GVKForObject(deployment, r.scheme)
+	if err != nil {
+		return fmt.Errorf("could not to retrieve group version kind: %v", err)
+	}
+	ownerRef := &metav1.OwnerReference{
+		APIVersion: gvk.GroupVersion().String(),
+		Kind:       gvk.Kind,
+		Name:       deployment.GetName(),
+		UID:        deployment.GetUID(),
+	}
+
+	return kubeSecrets.CreateKubernetesSecretFromItem(r.kubeClient, secretName, namespace, item, annotations[op.RestartDeploymentsAnnotation], secretLabels, secretType, ownerRef)
 }

pkg/controller/deployment/deployment_controller_test.go

@@ -281,7 +281,6 @@ var tests = []testReconcileItem{
 				Annotations: map[string]string{
 					op.VersionAnnotation:  fmt.Sprint(version),
 					op.ItemPathAnnotation: itemPath,
-					op.NameAnnotation:     name,
 				},
 			},
 			Data: expectedSecretData,
@@ -294,7 +293,6 @@ var tests = []testReconcileItem{
 				Annotations: map[string]string{
 					op.VersionAnnotation:  fmt.Sprint(version),
 					op.ItemPathAnnotation: itemPath,
-					op.NameAnnotation:     name,
 				},
 				Labels: map[string]string(nil),
 			},
@@ -385,7 +383,7 @@ var tests = []testReconcileItem{
 	},
 }
 
-func TestReconcileDepoyment(t *testing.T) {
+func TestReconcileDeployment(t *testing.T) {
 	for _, testData := range tests {
 		t.Run(testData.testName, func(t *testing.T) {
 

pkg/controller/onepassworditem/onepassworditem_controller.go

@@ -14,9 +14,11 @@ import (
 
 	corev1 "k8s.io/api/core/v1"
 	"k8s.io/apimachinery/pkg/api/errors"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/apimachinery/pkg/runtime"
 	ctrl "sigs.k8s.io/controller-runtime"
 	kubeClient "sigs.k8s.io/controller-runtime/pkg/client"
+	"sigs.k8s.io/controller-runtime/pkg/client/apiutil"
 	"sigs.k8s.io/controller-runtime/pkg/controller"
 	"sigs.k8s.io/controller-runtime/pkg/handler"
 	logf "sigs.k8s.io/controller-runtime/pkg/log"
@@ -94,10 +96,11 @@ func (r *ReconcileOnePasswordItem) Reconcile(request reconcile.Request) (reconci
 		}
 
 		// Handles creation or updating secrets for deployment if needed
-		if err := r.HandleOnePasswordItem(onepassworditem, request); err != nil {
-			return reconcile.Result{}, err
+		err := r.HandleOnePasswordItem(onepassworditem, request)
+		if updateStatusErr := r.updateStatus(onepassworditem, err); updateStatusErr != nil {
+			return reconcile.Result{}, fmt.Errorf("cannot update status: %s", updateStatusErr)
 		}
-		return reconcile.Result{}, nil
+		return reconcile.Result{}, err
 	}
 	// If one password finalizer exists then we must cleanup associated secrets
 	if utils.ContainsString(onepassworditem.ObjectMeta.Finalizers, finalizer) {
@@ -145,14 +148,56 @@ func (r *ReconcileOnePasswordItem) removeOnePasswordFinalizerFromOnePasswordItem
 func (r *ReconcileOnePasswordItem) HandleOnePasswordItem(resource *onepasswordv1.OnePasswordItem, request reconcile.Request) error {
 	secretName := resource.GetName()
 	labels := resource.Labels
-	annotations := resource.Annotations
 	secretType := resource.Type
-	autoRestart := annotations[op.RestartDeploymentsAnnotation]
+	autoRestart := resource.Annotations[op.RestartDeploymentsAnnotation]
 
 	item, err := onepassword.GetOnePasswordItemByPath(r.opConnectClient, resource.Spec.ItemPath)
 	if err != nil {
 		return fmt.Errorf("Failed to retrieve item: %v", err)
 	}
 
-	return kubeSecrets.CreateKubernetesSecretFromItem(r.kubeClient, secretName, resource.Namespace, item, autoRestart, labels, secretType, annotations)
+	// Create owner reference.
+	gvk, err := apiutil.GVKForObject(resource, r.scheme)
+	if err != nil {
+		return fmt.Errorf("could not to retrieve group version kind: %v", err)
+	}
+	ownerRef := &metav1.OwnerReference{
+		APIVersion: gvk.GroupVersion().String(),
+		Kind:       gvk.Kind,
+		Name:       resource.GetName(),
+		UID:        resource.GetUID(),
+	}
+
+	return kubeSecrets.CreateKubernetesSecretFromItem(r.kubeClient, secretName, resource.Namespace, item, autoRestart, labels, secretType, ownerRef)
+}
+
+func (r *ReconcileOnePasswordItem) updateStatus(resource *onepasswordv1.OnePasswordItem, err error) error {
+	existingCondition := findCondition(resource.Status.Conditions, onepasswordv1.OnePasswordItemReady)
+	updatedCondition := existingCondition
+	if err != nil {
+		updatedCondition.Message = err.Error()
+		updatedCondition.Status = metav1.ConditionFalse
+	} else {
+		updatedCondition.Message = ""
+		updatedCondition.Status = metav1.ConditionTrue
+	}
+
+	if existingCondition.Status != updatedCondition.Status {
+		updatedCondition.LastTransitionTime = metav1.Now()
+	}
+
+	resource.Status.Conditions = []onepasswordv1.OnePasswordItemCondition{updatedCondition}
+	return r.kubeClient.Status().Update(context.Background(), resource)
+}
+
+func findCondition(conditions []onepasswordv1.OnePasswordItemCondition, t onepasswordv1.OnePasswordItemConditionType) onepasswordv1.OnePasswordItemCondition {
+	for _, c := range conditions {
+		if c.Type == t {
+			return c
+		}
+	}
+	return onepasswordv1.OnePasswordItemCondition{
+		Type:   t,
+		Status: metav1.ConditionUnknown,
+	}
 }

pkg/controller/onepassworditem/onepassworditem_test.go

@@ -101,7 +101,7 @@ var tests = []testReconcileItem{
 		},
 	},
 	{
-		testName: "Test Do not update if OnePassword Version has not changed",
+		testName: "Test Do not update if OnePassword Version or VaultPath has not changed",
 		customResource: &onepasswordv1.OnePasswordItem{
 			TypeMeta: metav1.TypeMeta{
 				Kind:       onePasswordItemKind,

pkg/kubernetessecrets/kubernetes_secrets_builder.go

@@ -27,7 +27,6 @@ import (
 const OnepasswordPrefix = "operator.1password.io"
 const NameAnnotation = OnepasswordPrefix + "/item-name"
 const VersionAnnotation = OnepasswordPrefix + "/item-version"
-const restartAnnotation = OnepasswordPrefix + "/last-restarted"
 const ItemPathAnnotation = OnepasswordPrefix + "/item-path"
 const RestartDeploymentsAnnotation = OnepasswordPrefix + "/auto-restart"
 
@@ -35,29 +34,23 @@ var ErrCannotUpdateSecretType = errs.New("Cannot change secret type. Secret type
 
 var log = logf.Log
 
-func CreateKubernetesSecretFromItem(kubeClient kubernetesClient.Client, secretName, namespace string, item *onepassword.Item, autoRestart string, labels map[string]string, secretType string, secretAnnotations map[string]string) error {
-
+func CreateKubernetesSecretFromItem(kubeClient kubernetesClient.Client, secretName, namespace string, item *onepassword.Item, autoRestart string, labels map[string]string, secretType string, ownerRef *metav1.OwnerReference) error {
 	itemVersion := fmt.Sprint(item.Version)
-
-	// If secretAnnotations is nil we create an empty map so we can later assign values for the OP Annotations in the map
-	if secretAnnotations == nil {
-		secretAnnotations = map[string]string{}
+	secretAnnotations := map[string]string{
+		VersionAnnotation:  itemVersion,
+		ItemPathAnnotation: fmt.Sprintf("vaults/%v/items/%v", item.Vault.ID, item.ID),
 	}
 
-	secretAnnotations[VersionAnnotation] = itemVersion
-	secretAnnotations[ItemPathAnnotation] = fmt.Sprintf("vaults/%v/items/%v", item.Vault.ID, item.ID)
-
 	if autoRestart != "" {
 		_, err := utils.StringToBool(autoRestart)
 		if err != nil {
-			log.Error(err, "Error parsing %v annotation on Secret %v. Must be true or false. Defaulting to false.", RestartDeploymentsAnnotation, secretName)
-			return err
+			return fmt.Errorf("Error parsing %v annotation on Secret %v. Must be true or false. Defaulting to false.", RestartDeploymentsAnnotation, secretName)
 		}
 		secretAnnotations[RestartDeploymentsAnnotation] = autoRestart
 	}
 
 	// "Opaque" and "" secret types are treated the same by Kubernetes.
-	secret := BuildKubernetesSecretFromOnePasswordItem(secretName, namespace, secretAnnotations, labels, secretType, *item)
+	secret := BuildKubernetesSecretFromOnePasswordItem(secretName, namespace, secretAnnotations, labels, secretType, *item, ownerRef)
 
 	currentSecret := &corev1.Secret{}
 	err := kubeClient.Get(context.Background(), types.NamespacedName{Name: secret.Name, Namespace: secret.Namespace}, currentSecret)
@@ -68,32 +61,50 @@ func CreateKubernetesSecretFromItem(kubeClient kubernetesClient.Client, secretNa
 		return err
 	}
 
-	currentAnnotations := currentSecret.Annotations
-	currentLabels := currentSecret.Labels
+	// Check if the secret types are being changed on the update.
+	// Avoid Opaque and "" are treated as different on check.
+	wantSecretType := secretType
+	if wantSecretType == "" {
+		wantSecretType = string(corev1.SecretTypeOpaque)
+	}
 	currentSecretType := string(currentSecret.Type)
-	if !reflect.DeepEqual(currentSecretType, secretType) {
+	if currentSecretType == "" {
+		currentSecretType = string(corev1.SecretTypeOpaque)
+	}
+	if currentSecretType != wantSecretType {
 		return ErrCannotUpdateSecretType
 	}
 
+	currentAnnotations := currentSecret.Annotations
+	currentLabels := currentSecret.Labels
 	if !reflect.DeepEqual(currentAnnotations, secretAnnotations) || !reflect.DeepEqual(currentLabels, labels) {
 		log.Info(fmt.Sprintf("Updating Secret %v at namespace '%v'", secret.Name, secret.Namespace))
 		currentSecret.ObjectMeta.Annotations = secretAnnotations
 		currentSecret.ObjectMeta.Labels = labels
 		currentSecret.Data = secret.Data
-		return kubeClient.Update(context.Background(), currentSecret)
+		if err := kubeClient.Update(context.Background(), currentSecret); err != nil {
+			return fmt.Errorf("Kubernetes secret update failed: %w", err)
+		}
+		return nil
 	}
 
 	log.Info(fmt.Sprintf("Secret with name %v and version %v already exists", secret.Name, secret.Annotations[VersionAnnotation]))
 	return nil
 }
 
-func BuildKubernetesSecretFromOnePasswordItem(name, namespace string, annotations map[string]string, labels map[string]string, secretType string, item onepassword.Item) *corev1.Secret {
+func BuildKubernetesSecretFromOnePasswordItem(name, namespace string, annotations map[string]string, labels map[string]string, secretType string, item onepassword.Item, ownerRef *metav1.OwnerReference) *corev1.Secret {
+	var ownerRefs []metav1.OwnerReference
+	if ownerRef != nil {
+		ownerRefs = []metav1.OwnerReference{*ownerRef}
+	}
+
 	return &corev1.Secret{
 		ObjectMeta: metav1.ObjectMeta{
-			Name:        formatSecretName(name),
-			Namespace:   namespace,
-			Annotations: annotations,
-			Labels:      labels,
+			Name:            formatSecretName(name),
+			Namespace:       namespace,
+			Annotations:     annotations,
+			Labels:          labels,
+			OwnerReferences: ownerRefs,
 		},
 		Data: BuildKubernetesSecretData(item.Fields, item.Files),
 		Type: corev1.SecretType(secretType),

pkg/kubernetessecrets/kubernetes_secrets_builder_test.go

@@ -8,6 +8,7 @@ import (
 
 	"github.com/1Password/connect-sdk-go/onepassword"
 	corev1 "k8s.io/api/core/v1"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/apimachinery/pkg/types"
 	kubeValidate "k8s.io/apimachinery/pkg/util/validation"
 	"k8s.io/client-go/kubernetes"
@@ -32,12 +33,9 @@ func TestCreateKubernetesSecretFromOnePasswordItem(t *testing.T) {
 
 	kubeClient := fake.NewFakeClient()
 	secretLabels := map[string]string{}
-	secretAnnotations := map[string]string{
-		"testAnnotation": "exists",
-	}
 	secretType := ""
 
-	err := CreateKubernetesSecretFromItem(kubeClient, secretName, namespace, &item, restartDeploymentAnnotation, secretLabels, secretType, secretAnnotations)
+	err := CreateKubernetesSecretFromItem(kubeClient, secretName, namespace, &item, restartDeploymentAnnotation, secretLabels, secretType, nil)
 	if err != nil {
 		t.Errorf("Unexpected error: %v", err)
 	}
@@ -49,9 +47,50 @@ func TestCreateKubernetesSecretFromOnePasswordItem(t *testing.T) {
 	}
 	compareFields(item.Fields, createdSecret.Data, t)
 	compareAnnotationsToItem(createdSecret.Annotations, item, t)
+}
 
-	if createdSecret.Annotations["testAnnotation"] != "exists" {
-		t.Errorf("Expected testAnnotation to be merged with existing annotations, but wasn't.")
+func TestKubernetesSecretFromOnePasswordItemOwnerReferences(t *testing.T) {
+	secretName := "test-secret-name"
+	namespace := "test"
+
+	item := onepassword.Item{}
+	item.Fields = generateFields(5)
+	item.Version = 123
+	item.Vault.ID = "hfnjvi6aymbsnfc2xeeoheizda"
+	item.ID = "h46bb3jddvay7nxopfhvlwg35q"
+
+	kubeClient := fake.NewFakeClient()
+	secretLabels := map[string]string{}
+	secretType := ""
+
+	ownerRef := &metav1.OwnerReference{
+		Kind:       "Deployment",
+		APIVersion: "apps/v1",
+		Name:       "test-deployment",
+		UID:        types.UID("test-uid"),
+	}
+	err := CreateKubernetesSecretFromItem(kubeClient, secretName, namespace, &item, restartDeploymentAnnotation, secretLabels, secretType, ownerRef)
+	if err != nil {
+		t.Errorf("Unexpected error: %v", err)
+	}
+	createdSecret := &corev1.Secret{}
+	err = kubeClient.Get(context.Background(), types.NamespacedName{Name: secretName, Namespace: namespace}, createdSecret)
+
+	// Check owner references.
+	gotOwnerRefs := createdSecret.ObjectMeta.OwnerReferences
+	if len(gotOwnerRefs) != 1 {
+		t.Errorf("Expected owner references length: 1 but got: %d", len(gotOwnerRefs))
+	}
+
+	expOwnerRef := metav1.OwnerReference{
+		Kind:       "Deployment",
+		APIVersion: "apps/v1",
+		Name:       "test-deployment",
+		UID:        types.UID("test-uid"),
+	}
+	gotOwnerRef := gotOwnerRefs[0]
+	if gotOwnerRef != expOwnerRef {
+		t.Errorf("Expected owner reference value: %v but got: %v", expOwnerRef, gotOwnerRef)
 	}
 }
 
@@ -67,10 +106,9 @@ func TestUpdateKubernetesSecretFromOnePasswordItem(t *testing.T) {
 
 	kubeClient := fake.NewFakeClient()
 	secretLabels := map[string]string{}
-	secretAnnotations := map[string]string{}
 	secretType := ""
 
-	err := CreateKubernetesSecretFromItem(kubeClient, secretName, namespace, &item, restartDeploymentAnnotation, secretLabels, secretType, secretAnnotations)
+	err := CreateKubernetesSecretFromItem(kubeClient, secretName, namespace, &item, restartDeploymentAnnotation, secretLabels, secretType, nil)
 
 	if err != nil {
 		t.Errorf("Unexpected error: %v", err)
@@ -82,7 +120,7 @@ func TestUpdateKubernetesSecretFromOnePasswordItem(t *testing.T) {
 	newItem.Version = 456
 	newItem.Vault.ID = "hfnjvi6aymbsnfc2xeeoheizda"
 	newItem.ID = "h46bb3jddvay7nxopfhvlwg35q"
-	err = CreateKubernetesSecretFromItem(kubeClient, secretName, namespace, &newItem, restartDeploymentAnnotation, secretLabels, secretType, secretAnnotations)
+	err = CreateKubernetesSecretFromItem(kubeClient, secretName, namespace, &newItem, restartDeploymentAnnotation, secretLabels, secretType, nil)
 	if err != nil {
 		t.Errorf("Unexpected error: %v", err)
 	}
@@ -118,7 +156,7 @@ func TestBuildKubernetesSecretFromOnePasswordItem(t *testing.T) {
 	labels := map[string]string{}
 	secretType := ""
 
-	kubeSecret := BuildKubernetesSecretFromOnePasswordItem(name, namespace, annotations, labels, secretType, item)
+	kubeSecret := BuildKubernetesSecretFromOnePasswordItem(name, namespace, annotations, labels, secretType, item, nil)
 	if kubeSecret.Name != strings.ToLower(name) {
 		t.Errorf("Expected name value: %v but got: %v", name, kubeSecret.Name)
 	}
@@ -153,7 +191,7 @@ func TestBuildKubernetesSecretFixesInvalidLabels(t *testing.T) {
 		},
 	}
 
-	kubeSecret := BuildKubernetesSecretFromOnePasswordItem(name, namespace, annotations, labels, secretType, item)
+	kubeSecret := BuildKubernetesSecretFromOnePasswordItem(name, namespace, annotations, labels, secretType, item, nil)
 
 	// Assert Secret's meta.name was fixed
 	if kubeSecret.Name != expectedName {
@@ -183,12 +221,9 @@ func TestCreateKubernetesTLSSecretFromOnePasswordItem(t *testing.T) {
 
 	kubeClient := fake.NewFakeClient()
 	secretLabels := map[string]string{}
-	secretAnnotations := map[string]string{
-		"testAnnotation": "exists",
-	}
 	secretType := "kubernetes.io/tls"
 
-	err := CreateKubernetesSecretFromItem(kubeClient, secretName, namespace, &item, restartDeploymentAnnotation, secretLabels, secretType, secretAnnotations)
+	err := CreateKubernetesSecretFromItem(kubeClient, secretName, namespace, &item, restartDeploymentAnnotation, secretLabels, secretType, nil)
 	if err != nil {
 		t.Errorf("Unexpected error: %v", err)
 	}

pkg/onepassword/secret_update_handler.go

@@ -5,6 +5,8 @@ import (
 	"fmt"
 	"time"
 
+	v1 "github.com/1Password/onepassword-operator/pkg/apis/onepassword/v1"
+
 	kubeSecrets "github.com/1Password/onepassword-operator/pkg/kubernetessecrets"
 	"github.com/1Password/onepassword-operator/pkg/utils"
 
@@ -89,9 +91,10 @@ func (h *SecretUpdateHandler) restartDeploymentsWithUpdatedSecrets(updatedSecret
 
 func (h *SecretUpdateHandler) restartDeployment(deployment *appsv1.Deployment) {
 	log.Info(fmt.Sprintf("Deployment %q at namespace %q references an updated secret. Restarting", deployment.GetName(), deployment.Namespace))
-	deployment.Spec.Template.Annotations = map[string]string{
-		RestartAnnotation: time.Now().String(),
+	if deployment.Spec.Template.Annotations == nil {
+		deployment.Spec.Template.Annotations = map[string]string{}
 	}
+	deployment.Spec.Template.Annotations[RestartAnnotation] = time.Now().String()
 	err := h.client.Update(context.Background(), deployment)
 	if err != nil {
 		log.Error(err, "Problem restarting deployment")
@@ -116,24 +119,37 @@ func (h *SecretUpdateHandler) updateKubernetesSecrets() (map[string]map[string]*
 			continue
 		}
 
-		item, err := GetOnePasswordItemByPath(h.opConnectClient, secret.Annotations[ItemPathAnnotation])
+		OnePasswordItemPath := h.getPathFromOnePasswordItem(secret)
+
+		item, err := GetOnePasswordItemByPath(h.opConnectClient, OnePasswordItemPath)
 		if err != nil {
 			log.Error(err, "failed to retrieve 1Password item at path \"%s\" for secret \"%s\"", secret.Annotations[ItemPathAnnotation], secret.Name)
 			continue
 		}
 
 		itemVersion := fmt.Sprint(item.Version)
-		if currentVersion != itemVersion {
+		itemPathString := fmt.Sprintf("vaults/%v/items/%v", item.Vault.ID, item.ID)
+
+		if currentVersion != itemVersion || secret.Annotations[ItemPathAnnotation] != itemPathString {
 			if isItemLockedForForcedRestarts(item) {
 				log.Info(fmt.Sprintf("Secret '%v' has been updated in 1Password but is set to be ignored. Updates to an ignored secret will not trigger an update to a kubernetes secret or a rolling restart.", secret.GetName()))
 				secret.Annotations[VersionAnnotation] = itemVersion
-				h.client.Update(context.Background(), &secret)
+				secret.Annotations[ItemPathAnnotation] = itemPathString
+				if err := h.client.Update(context.Background(), &secret); err != nil {
+					log.Error(err, "failed to update secret %s annotations to version %d: %s", secret.Name, itemVersion, err)
+					continue
+				}
 				continue
 			}
 			log.Info(fmt.Sprintf("Updating kubernetes secret '%v'", secret.GetName()))
 			secret.Annotations[VersionAnnotation] = itemVersion
-			updatedSecret := kubeSecrets.BuildKubernetesSecretFromOnePasswordItem(secret.Name, secret.Namespace, secret.Annotations, secret.Labels, string(secret.Type), *item)
-			h.client.Update(context.Background(), updatedSecret)
+			secret.Annotations[ItemPathAnnotation] = itemPathString
+			secret.Data = kubeSecrets.BuildKubernetesSecretData(item.Fields, item.Files)
+			log.Info(fmt.Sprintf("New secret path: %v and version: %v", secret.Annotations[ItemPathAnnotation], secret.Annotations[VersionAnnotation]))
+			if err := h.client.Update(context.Background(), &secret); err != nil {
+				log.Error(err, "failed to update secret %s to version %d: %s", secret.Name, itemVersion, err)
+				continue
+			}
 			if updatedSecrets[secret.Namespace] == nil {
 				updatedSecrets[secret.Namespace] = make(map[string]*corev1.Secret)
 			}
@@ -177,6 +193,22 @@ func (h *SecretUpdateHandler) getIsSetForAutoRestartByNamespaceMap() (map[string
 	return namespacesMap, nil
 }
 
+func (h *SecretUpdateHandler) getPathFromOnePasswordItem(secret corev1.Secret) string {
+	onePasswordItem := &v1.OnePasswordItem{}
+
+	// Search for our original OnePasswordItem if it exists
+	err := h.client.Get(context.TODO(), client.ObjectKey{
+		Namespace: secret.Namespace,
+		Name:      secret.Name}, onePasswordItem)
+
+	if err == nil {
+		return onePasswordItem.Spec.ItemPath
+	}
+
+	// If we can't find the OnePassword Item we'll just return the annotation from the secret item.
+	return secret.Annotations[ItemPathAnnotation]
+}
+
 func isSecretSetForAutoRestart(secret *corev1.Secret, deployment *appsv1.Deployment, setForAutoRestartByNamespace map[string]bool) bool {
 	restartDeployment := secret.Annotations[RestartDeploymentsAnnotation]
 	//If annotation for auto restarts for deployment is not set. Check for the annotation on its namepsace

pkg/onepassword/secret_update_handler_test.go

@@ -122,6 +122,9 @@ var tests = []testUpdateSecretTask{
 			},
 			Spec: appsv1.DeploymentSpec{
 				Template: corev1.PodTemplateSpec{
+					ObjectMeta: metav1.ObjectMeta{
+						Annotations: map[string]string{"external-annotation": "some-value"},
+					},
 					Spec: corev1.PodSpec{
 						Containers: []corev1.Container{
 							{
@@ -235,6 +238,9 @@ var tests = []testUpdateSecretTask{
 			},
 			Spec: appsv1.DeploymentSpec{
 				Template: corev1.PodTemplateSpec{
+					ObjectMeta: metav1.ObjectMeta{
+						Annotations: map[string]string{"external-annotation": "some-value"},
+					},
 					Spec: corev1.PodSpec{
 						Volumes: []corev1.Volume{
 							{
@@ -342,6 +348,9 @@ var tests = []testUpdateSecretTask{
 			},
 			Spec: appsv1.DeploymentSpec{
 				Template: corev1.PodTemplateSpec{
+					ObjectMeta: metav1.ObjectMeta{
+						Annotations: map[string]string{"external-annotation": "some-value"},
+					},
 					Spec: corev1.PodSpec{
 						Containers: []corev1.Container{
 							{
@@ -411,6 +420,9 @@ var tests = []testUpdateSecretTask{
 			},
 			Spec: appsv1.DeploymentSpec{
 				Template: corev1.PodTemplateSpec{
+					ObjectMeta: metav1.ObjectMeta{
+						Annotations: map[string]string{"external-annotation": "some-value"},
+					},
 					Spec: corev1.PodSpec{
 						Containers: []corev1.Container{
 							{
@@ -482,6 +494,9 @@ var tests = []testUpdateSecretTask{
 			},
 			Spec: appsv1.DeploymentSpec{
 				Template: corev1.PodTemplateSpec{
+					ObjectMeta: metav1.ObjectMeta{
+						Annotations: map[string]string{"external-annotation": "some-value"},
+					},
 					Spec: corev1.PodSpec{
 						Containers: []corev1.Container{
 							{
@@ -553,6 +568,9 @@ var tests = []testUpdateSecretTask{
 			},
 			Spec: appsv1.DeploymentSpec{
 				Template: corev1.PodTemplateSpec{
+					ObjectMeta: metav1.ObjectMeta{
+						Annotations: map[string]string{"external-annotation": "some-value"},
+					},
 					Spec: corev1.PodSpec{
 						Containers: []corev1.Container{
 							{
@@ -630,6 +648,9 @@ var tests = []testUpdateSecretTask{
 			},
 			Spec: appsv1.DeploymentSpec{
 				Template: corev1.PodTemplateSpec{
+					ObjectMeta: metav1.ObjectMeta{
+						Annotations: map[string]string{"external-annotation": "some-value"},
+					},
 					Spec: corev1.PodSpec{
 						Containers: []corev1.Container{
 							{
@@ -703,6 +724,9 @@ var tests = []testUpdateSecretTask{
 			},
 			Spec: appsv1.DeploymentSpec{
 				Template: corev1.PodTemplateSpec{
+					ObjectMeta: metav1.ObjectMeta{
+						Annotations: map[string]string{"external-annotation": "some-value"},
+					},
 					Spec: corev1.PodSpec{
 						Containers: []corev1.Container{
 							{
@@ -829,6 +853,16 @@ func TestUpdateSecretHandler(t *testing.T) {
 			} else {
 				assert.False(t, testData.expectedRestart, "Deployment was restarted but should not have been.")
 			}
+
+			oldPodTemplateAnnotations := testData.existingDeployment.Spec.Template.ObjectMeta.Annotations
+			newPodTemplateAnnotations := deployment.Spec.Template.Annotations
+			for name, expected := range oldPodTemplateAnnotations {
+				actual, ok := newPodTemplateAnnotations[name]
+				if assert.Truef(t, ok, "Annotation %s was present in original pod template but was dropped after update", name) {
+					assert.Equalf(t, expected, actual, "Annotation value for %s original pod template has changed", name)
+					continue
+				}
+			}
 		})
 	}
 }