Merge pull request #78 from 1Password/autorestart-webhook

Preparing Operator to handle Deployments that use the Kubernetes Webhook

Makefile

@@ -19,17 +19,17 @@ test:	## Run test suite
 test/coverage:	## Run test suite with coverage report
 	go test -v ./... -cover
 
-build:	## Build operator Docker image
+build/operator:	## Build operator Docker image
-	@docker build -f Dockerfile --build-arg operator_version=$(curVersion) -t $(DOCKER_IMG_TAG) .
+	@docker build -f operator/Dockerfile --build-arg operator_version=$(curVersion) -t $(DOCKER_IMG_TAG) .
 	@echo "Successfully built and tagged image."
 	@echo "Tag: $(DOCKER_IMG_TAG)"
 
-build/local:	## Build local version of the operator Docker image
+build/operator/local:	## Build local version of the operator Docker image 
-	@docker build -f Dockerfile -t local/$(DOCKER_IMG_TAG) .
+	@docker build -f operator/Dockerfile -t local/$(DOCKER_IMG_TAG) .
 
-build/binary: clean	## Build operator binary
+build/operator/binary: clean	## Build operator binary
 	@mkdir -p dist
-	@go build -mod vendor -a -o manager ./cmd/manager/main.go
+	@go build -mod vendor -a -o manager ./operator/cmd/manager/main.go
 	@mv manager ./dist
 
 clean:

README.md

@@ -1,4 +1,8 @@
-# 1Password Connect Kubernetes Operator
+# 1Password for Kubernetes
+
+This repository includes various tooling for integrating 1Password secrets wtih Kubernetes.
+
+## 1Password Connect Kubernetes Operator
 
 The 1Password Connect Kubernetes Operator provides the ability to integrate Kubernetes with 1Password. This Operator manages `OnePasswordItem` Custom Resource Definitions (CRDs) that define the location of an Item stored in 1Password. The `OnePasswordItem` CRD, when created, will be used to compose a Kubernetes Secret containing the contents of the specified item.
 
@@ -6,227 +10,10 @@ The 1Password Connect Kubernetes Operator also allows for Kubernetes Secrets to
 
 The 1Password Connect Kubernetes Operator will continually check for updates from 1Password for any Kubernetes Secret that it has generated. If a Kubernetes Secret is updated, any Deployment using that secret can be automatically restarted.
 
-## Setup
+[Click here for more details on the 1Password Kubernetes Operator](operator/README.md)
-
-Prerequisites:
-
-- [1Password Command Line Tool Installed](https://1password.com/downloads/command-line/)
-- [kubectl installed](https://kubernetes.io/docs/tasks/tools/install-kubectl/)
-- [docker installed](https://docs.docker.com/get-docker/)
-- [Generated a 1password-credentials.json file and issued a 1Password Connect API Token for the K8s Operator integration](https://support.1password.com/secrets-automation/)
-- [1Password Connect deployed to Kubernetes](https://support.1password.com/connect-deploy-kubernetes/#step-2-deploy-a-1password-connect-server). **NOTE**: If customization of the 1Password Connect deployment is not required you can skip this prerequisite.
-
-### Quickstart for Deploying 1Password Connect to Kubernetes
 
 
-#### Deploy with Helm
+# Security
-The 1Password Connect Helm Chart helps to simplify the deployment of 1Password Connect and the 1Password Connect Kubernetes Operator to Kubernetes. 
-
-[The 1Password Connect Helm Chart can be found here.](https://github.com/1Password/connect-helm-charts)
-
-#### Deploy using the Connect Operator
-If 1Password Connect is already running, you can skip this step. This guide will provide a quickstart option for deploying a default configuration of 1Password Connect via starting the deploying the 1Password Connect Operator, however it is recommended that you instead deploy your own manifest file if customization of the 1Password Connect deployment is desired.
-
-Encode the 1password-credentials.json file you generated in the prerequisite steps and save it to a file named op-session:
-
-```bash
-$ cat 1password-credentials.json | base64 | \
-  tr '/+' '_-' | tr -d '=' | tr -d '\n' > op-session
-```
-
-Create a Kubernetes secret from the op-session file:
-```bash
-
-$  kubectl create secret generic op-credentials --from-file=1password-credentials.json
-```
-
-Add the following environment variable to the onepassword-connect-operator container in `deploy/operator.yaml`:
-```yaml
-- name: MANAGE_CONNECT
-  value: "true"
-```
-Adding this environment variable will have the operator automatically deploy a default configuration of 1Password Connect to the `default` namespace.
-### Kubernetes Operator Deployment
-
-**Create Kubernetes Secret for OP_CONNECT_TOKEN**
-
-"Create a Connect token for the operator and save it as a Kubernetes Secret: 
-
-```bash
-$ kubectl create secret generic onepassword-token --from-literal=token=<OP_CONNECT_TOKEN>"
-```
-
-If you do not have a token for the operator, you can generate a token and save it to kubernetes with the following command:
-```bash
-$ kubectl create secret generic onepassword-token --from-literal=token=$(op create connect token <server> op-k8s-operator --vault <vault>)
-```
-
-[More information on generating a token can be found here](https://support.1password.com/secrets-automation/#appendix-issue-additional-access-tokens)
-
-**Set Permissions For Operator**
-
-We must create a service account, role, and role binding and Kubernetes. Examples can be found in the `/deploy` folder.
-
-```bash
-$ kubectl apply -f deploy/permissions.yaml
-```
-
-**Create Custom One Password Secret Resource**
-
-```bash
-$ kubectl apply -f deploy/crds/onepassword.com_onepassworditems_crd.yaml
-```
-
-**Deploying the Operator**
-
-An sample Deployment yaml can be found at `/deploy/operator.yaml`.
-
-
-To further configure the 1Password Kubernetes Operator the Following Environment variables can be set in the operator yaml:
-
-- **OP_CONNECT_HOST** (required): Specifies the host name within Kubernetes in which to access the 1Password Connect.
-- **WATCH_NAMESPACE:** (default: watch all namespaces): Comma separated list of what Namespaces to watch for changes.
-- **POLLING_INTERVAL** (default: 600): The number of seconds the 1Password Kubernetes Operator will wait before checking for updates from 1Password Connect.
-- **MANAGE_CONNECT** (default: false): If set to true, on deployment of the operator, a default configuration of the OnePassword Connect Service will be deployed to the `default` namespace.
-- **AUTO_RESTART** (default: false): If set to true, the operator will restart any deployment using a secret from 1Password Connect. This can be overwritten by namespace, deployment, or individual secret. More details on AUTO_RESTART can be found in the ["Configuring Automatic Rolling Restarts of Deployments"](#configuring-automatic-rolling-restarts-of-deployments) section.
-
-Apply the deployment file:
-
-```yaml
-kubectl apply -f deploy/operator.yaml
-```
-
-## Usage
-
-To create a Kubernetes Secret from a 1Password item, create a yaml file with the following
-
-```yaml
-apiVersion: onepassword.com/v1
-kind: OnePasswordItem
-metadata:
-  name: <item_name> #this name will also be used for naming the generated kubernetes secret
-spec:
-  itemPath: "vaults/<vault_id_or_title>/items/<item_id_or_title>" 
-```
-
-Deploy the OnePasswordItem to Kubernetes:
-
-```bash
-$ kubectl apply -f <your_item>.yaml
-```
-
-To test that the Kubernetes Secret check that the following command returns a secret:
-
-```bash
-$ kubectl get secret <secret_name>
-```
-
-Note: Deleting the `OnePasswordItem` that you've created will automatically delete the created Kubernetes Secret.
-
-To create a single Kubernetes Secret for a deployment, add the following annotations to the deployment metadata:
-
-```yaml
-apiVersion: apps/v1
-kind: Deployment
-metadata:
-  name: deployment-example
-  annotations:
-    operator.1password.io/item-path: "vaults/<vault_id_or_title>/items/<item_id_or_title>"
-    operator.1password.io/item-name: "<secret_name>"
-```
-
-Applying this yaml file will create a Kubernetes Secret with the name `<secret_name>` and contents from the location specified at the specified Item Path.
-
-Note: Deleting the Deployment that you've created will automatically delete the created Kubernetes Secret only if the deployment is still annotated with `operator.1password.io/item-path` and `operator.1password.io/item-name` and no other deployment is using the secret.
-
-If a 1Password Item that is linked to a Kubernetes Secret is updated within the POLLING_INTERVAL the associated Kubernetes Secret will be updated. However, if you do not want a specific secret to be updated you can add the tag `operator.1password.io:ignore-secret` to the item stored in 1Password. While this tag is in place, any updates made to an item will not trigger an update to the associated secret in Kubernetes.
-
----
-**NOTE**
-
-If multiple 1Password vaults/items have the same `title` when using a title in the access path, the desired action will be performed on the oldest vault/item. 
-
-Titles and field names that include white space and other characters that are not a valid [DNS subdomain name](https://kubernetes.io/docs/concepts/configuration/secret/) will create Kubernetes secrets that have titles and fields in the following format:
- - Invalid characters before the first alphanumeric character and after the last alphanumeric character will be removed
- - All whitespaces between words will be replaced by `-`
- - All the letters will be lower-cased.
-
----
-
-### Configuring Automatic Rolling Restarts of Deployments
-
-If a 1Password Item that is linked to a Kubernetes Secret is updated, any deployments configured to `auto-restart` AND are using that secret will be given a rolling restart the next time 1Password Connect is polled for updates.
-
-There are many levels of granularity on which to configure auto restarts on deployments: at the operator level, per-namespace, or per-deployment.
-
-**On the operator**: This method allows for managing auto restarts on all deployments within the namespaces watched by operator. Auto restarts can be enabled by setting the environemnt variable  `AUTO_RESTART` to true. If the value is not set, the operator will default this value to false.
-
-**Per Namespace**: This method allows for managing auto restarts on all deployments within a namespace. Auto restarts can by managed by setting the annotation `operator.1password.io/auto-restart` to either `true` or `false` on the desired namespace. An example of this is shown below:
-```yaml
-# enabled auto restarts for all deployments within a namespace unless overwritten within a deployment
-apiVersion: v1
-kind: Namespace
-metadata:
-  name: "example-namespace"
-  annotations:
-    operator.1password.io/auto-restart: "true"
-```
-If the value is not set, the auto reset settings on the operator will be used. This value can be overwritten by deployment.
-
-**Per Deployment**
-This method allows for managing auto restarts on a given deployment. Auto restarts can by managed by setting the annotation `operator.1password.io/auto-restart` to either `true` or `false` on the desired deployment. An example of this is shown below:
-```yaml
-# enabled auto restarts for the deployment
-apiVersion: v1
-kind: Deployment
-metadata:
-  name: "example-deployment"
-  annotations:
-    operator.1password.io/auto-restart: "true"
-```
-If the value is not set, the auto reset settings on the namespace will be used.
-
-**Per OnePasswordItem Custom Resource**
-This method allows for managing auto restarts on a given OnePasswordItem custom resource. Auto restarts can by managed by setting the annotation `operator.1password.io/auto_restart` to either `true` or `false` on the desired OnePasswordItem. An example of this is shown below:
-```yaml
-# enabled auto restarts for the OnePasswordItem
-apiVersion: onepassword.com/v1
-kind: OnePasswordItem
-metadata:
-  name: example
-  annotations:
-    operator.1password.io/auto-restart: "true"
-```
-If the value is not set, the auto reset settings on the deployment will be used.
-
-## Development
-
-### Creating a Docker image
-
-To create a local version of the Docker image for testing, use the following `Makefile` target:
-```shell
-make build/local
-```
-
-### Building the Operator binary
-```shell
-make build/binary
-```
-
-The binary will be placed inside a `dist` folder within this repository.
-
-### Running Tests
-
-```shell
-make test
-```
-
-With coverage:
-```shell
-make test/coverage
-```
-
-## Security
 
 1Password requests you practice responsible disclosure if you discover a vulnerability. 
 

build/Dockerfile

@@ -1,15 +0,0 @@
-FROM registry.access.redhat.com/ubi8/ubi-minimal:latest
-
-ENV OPERATOR=/usr/local/bin/onepassword-connect-operator \
-    USER_UID=1001 \
-    USER_NAME=onepassword-connect-operator
-
-# install operator binary
-COPY build/_output/bin/op-kubernetes-connect-operator ${OPERATOR}
-
-COPY build/bin /usr/local/bin
-RUN  /usr/local/bin/user_setup
-
-ENTRYPOINT ["/usr/local/bin/entrypoint"]
-
-USER ${USER_UID}

build/bin/entrypoint

@@ -1,3 +0,0 @@
-#!/bin/sh -e
-
-exec ${OPERATOR} $@

build/bin/user_setup

@@ -1,11 +0,0 @@
-#!/bin/sh
-set -x
-
-# ensure $HOME exists and is accessible by group 0 (we don't know what the runtime UID will be)
-echo "${USER_NAME}:x:${USER_UID}:0:${USER_NAME} user:${HOME}:/sbin/nologin" >> /etc/passwd
-mkdir -p "${HOME}"
-chown "${USER_UID}:0" "${HOME}"
-chmod ug+rwx "${HOME}"
-
-# no need for this script to remain in the image after running
-rm "$0"

operator/Dockerfile

@@ -7,18 +7,18 @@ COPY go.mod go.mod
 COPY go.sum go.sum
 
 # Copy the go source
-COPY cmd/manager/main.go main.go
+COPY operator/cmd/manager/main.go operator/main.go
-COPY pkg/ pkg/
+COPY operator/pkg/ operator/pkg/
-COPY version/ version/
+COPY operator/version/ operator/version/
 COPY vendor/ vendor/
 # Build
 ARG operator_version=dev
 RUN CGO_ENABLED=0 \
     GO111MODULE=on \
     go build \
-    -ldflags "-X \"github.com/1Password/onepassword-operator/version.Version=$operator_version\"" \
+    -ldflags "-X \"github.com/1Password/onepassword-operator/operator/version.Version=$operator_version\"" \
     -mod vendor \
-    -a -o manager main.go
+    -a -o manager operator/main.go
 
 # Use distroless as minimal base image to package the manager binary
 # Refer to https://github.com/GoogleContainerTools/distroless for more details
@@ -26,6 +26,6 @@ FROM gcr.io/distroless/static:nonroot
 WORKDIR /
 COPY --from=builder /workspace/manager .
 USER nonroot:nonroot
-COPY deploy/connect/ deploy/connect/
+COPY operator/deploy/connect/ operator/deploy/connect/
 
 ENTRYPOINT ["/manager"]

operator/README.md

@@ -0,0 +1,235 @@
+# 1Password Connect Kubernetes Operator
+
+The 1Password Connect Kubernetes Operator provides the ability to integrate Kubernetes with 1Password. This Operator manages `OnePasswordItem` Custom Resource Definitions (CRDs) that define the location of an Item stored in 1Password. The `OnePasswordItem` CRD, when created, will be used to compose a Kubernetes Secret containing the contents of the specified item.
+
+The 1Password Connect Kubernetes Operator also allows for Kubernetes Secrets to be composed from a 1Password Item through annotation of an Item Path on a deployment.
+
+The 1Password Connect Kubernetes Operator will continually check for updates from 1Password for any Kubernetes Secret that it has generated. If a Kubernetes Secret is updated, any Deployment using that secret can be automatically restarted.
+
+## Setup
+
+Prerequisites:
+
+- [1Password Command Line Tool Installed](https://1password.com/downloads/command-line/)
+- [kubectl installed](https://kubernetes.io/docs/tasks/tools/install-kubectl/)
+- [docker installed](https://docs.docker.com/get-docker/)
+- [Generated a 1password-credentials.json file and issued a 1Password Connect API Token for the K8s Operator integration](https://support.1password.com/secrets-automation/)
+- [1Password Connect deployed to Kubernetes](https://support.1password.com/connect-deploy-kubernetes/#step-2-deploy-a-1password-connect-server). **NOTE**: If customization of the 1Password Connect deployment is not required you can skip this prerequisite.
+
+### Quickstart for Deploying 1Password Connect to Kubernetes
+
+
+#### Deploy with Helm
+The 1Password Connect Helm Chart helps to simplify the deployment of 1Password Connect and the 1Password Connect Kubernetes Operator to Kubernetes. 
+
+[The 1Password Connect Helm Chart can be found here.](https://github.com/1Password/connect-helm-charts)
+
+#### Deploy using the Connect Operator
+If 1Password Connect is already running, you can skip this step. This guide will provide a quickstart option for deploying a default configuration of 1Password Connect via starting the deploying the 1Password Connect Operator, however it is recommended that you instead deploy your own manifest file if customization of the 1Password Connect deployment is desired.
+
+Encode the 1password-credentials.json file you generated in the prerequisite steps and save it to a file named op-session:
+
+```bash
+$ cat 1password-credentials.json | base64 | \
+  tr '/+' '_-' | tr -d '=' | tr -d '\n' > op-session
+```
+
+Create a Kubernetes secret from the op-session file:
+```bash
+
+$  kubectl create secret generic op-credentials --from-file=1password-credentials.json
+```
+
+Add the following environment variable to the onepassword-connect-operator container in `deploy/operator.yaml`:
+```yaml
+- name: MANAGE_CONNECT
+  value: "true"
+```
+Adding this environment variable will have the operator automatically deploy a default configuration of 1Password Connect to the `default` namespace.
+### Kubernetes Operator Deployment
+
+**Create Kubernetes Secret for OP_CONNECT_TOKEN**
+
+"Create a Connect token for the operator and save it as a Kubernetes Secret: 
+
+```bash
+$ kubectl create secret generic onepassword-token --from-literal=token=<OP_CONNECT_TOKEN>"
+```
+
+If you do not have a token for the operator, you can generate a token and save it to kubernetes with the following command:
+```bash
+$ kubectl create secret generic onepassword-token --from-literal=token=$(op create connect token <server> op-k8s-operator --vault <vault>)
+```
+
+[More information on generating a token can be found here](https://support.1password.com/secrets-automation/#appendix-issue-additional-access-tokens)
+
+**Set Permissions For Operator**
+
+We must create a service account, role, and role binding and Kubernetes. Examples can be found in the `/deploy` folder.
+
+```bash
+$ kubectl apply -f deploy/permissions.yaml
+```
+
+**Create Custom One Password Secret Resource**
+
+```bash
+$ kubectl apply -f deploy/crds/onepassword.com_onepassworditems_crd.yaml
+```
+
+**Deploying the Operator**
+
+An sample Deployment yaml can be found at `/deploy/operator.yaml`.
+
+
+To further configure the 1Password Kubernetes Operator the Following Environment variables can be set in the operator yaml:
+
+- **OP_CONNECT_HOST** (required): Specifies the host name within Kubernetes in which to access the 1Password Connect.
+- **WATCH_NAMESPACE:** (default: watch all namespaces): Comma separated list of what Namespaces to watch for changes.
+- **POLLING_INTERVAL** (default: 600): The number of seconds the 1Password Kubernetes Operator will wait before checking for updates from 1Password Connect.
+- **MANAGE_CONNECT** (default: false): If set to true, on deployment of the operator, a default configuration of the OnePassword Connect Service will be deployed to the `default` namespace.
+- **AUTO_RESTART** (default: false): If set to true, the operator will restart any deployment using a secret from 1Password Connect. This can be overwritten by namespace, deployment, or individual secret. More details on AUTO_RESTART can be found in the ["Configuring Automatic Rolling Restarts of Deployments"](#configuring-automatic-rolling-restarts-of-deployments) section.
+
+Apply the deployment file:
+
+```yaml
+kubectl apply -f deploy/operator.yaml
+```
+
+## Usage
+
+To create a Kubernetes Secret from a 1Password item, create a yaml file with the following
+
+```yaml
+apiVersion: onepassword.com/v1
+kind: OnePasswordItem
+metadata:
+  name: <item_name> #this name will also be used for naming the generated kubernetes secret
+spec:
+  itemPath: "vaults/<vault_id_or_title>/items/<item_id_or_title>" 
+```
+
+Deploy the OnePasswordItem to Kubernetes:
+
+```bash
+$ kubectl apply -f <your_item>.yaml
+```
+
+To test that the Kubernetes Secret check that the following command returns a secret:
+
+```bash
+$ kubectl get secret <secret_name>
+```
+
+Note: Deleting the `OnePasswordItem` that you've created will automatically delete the created Kubernetes Secret.
+
+To create a single Kubernetes Secret for a deployment, add the following annotations to the deployment metadata:
+
+```yaml
+apiVersion: apps/v1
+kind: Deployment
+metadata:
+  name: deployment-example
+  annotations:
+    operator.1password.io/item-path: "vaults/<vault_id_or_title>/items/<item_id_or_title>"
+    operator.1password.io/item-name: "<secret_name>"
+```
+
+Applying this yaml file will create a Kubernetes Secret with the name `<secret_name>` and contents from the location specified at the specified Item Path.
+
+Note: Deleting the Deployment that you've created will automatically delete the created Kubernetes Secret only if the deployment is still annotated with `operator.1password.io/item-path` and `operator.1password.io/item-name` and no other deployment is using the secret.
+
+If a 1Password Item that is linked to a Kubernetes Secret is updated within the POLLING_INTERVAL the associated Kubernetes Secret will be updated. However, if you do not want a specific secret to be updated you can add the tag `operator.1password.io:ignore-secret` to the item stored in 1Password. While this tag is in place, any updates made to an item will not trigger an update to the associated secret in Kubernetes.
+
+---
+**NOTE**
+
+If multiple 1Password vaults/items have the same `title` when using a title in the access path, the desired action will be performed on the oldest vault/item. 
+
+Titles and field names that include white space and other characters that are not a valid [DNS subdomain name](https://kubernetes.io/docs/concepts/configuration/secret/) will create Kubernetes secrets that have titles and fields in the following format:
+ - Invalid characters before the first alphanumeric character and after the last alphanumeric character will be removed
+ - All whitespaces between words will be replaced by `-`
+ - All the letters will be lower-cased.
+
+---
+
+### Configuring Automatic Rolling Restarts of Deployments
+
+If a 1Password Item that is linked to a Kubernetes Secret is updated, any deployments configured to `auto-restart` AND are using that secret will be given a rolling restart the next time 1Password Connect is polled for updates.
+
+There are many levels of granularity on which to configure auto restarts on deployments: at the operator level, per-namespace, or per-deployment.
+
+**On the operator**: This method allows for managing auto restarts on all deployments within the namespaces watched by operator. Auto restarts can be enabled by setting the environemnt variable  `AUTO_RESTART` to true. If the value is not set, the operator will default this value to false.
+
+**Per Namespace**: This method allows for managing auto restarts on all deployments within a namespace. Auto restarts can by managed by setting the annotation `operator.1password.io/auto-restart` to either `true` or `false` on the desired namespace. An example of this is shown below:
+```yaml
+# enabled auto restarts for all deployments within a namespace unless overwritten within a deployment
+apiVersion: v1
+kind: Namespace
+metadata:
+  name: "example-namespace"
+  annotations:
+    operator.1password.io/auto-restart: "true"
+```
+If the value is not set, the auto reset settings on the operator will be used. This value can be overwritten by deployment.
+
+**Per Deployment**
+This method allows for managing auto restarts on a given deployment. Auto restarts can by managed by setting the annotation `operator.1password.io/auto-restart` to either `true` or `false` on the desired deployment. An example of this is shown below:
+```yaml
+# enabled auto restarts for the deployment
+apiVersion: v1
+kind: Deployment
+metadata:
+  name: "example-deployment"
+  annotations:
+    operator.1password.io/auto-restart: "true"
+```
+If the value is not set, the auto reset settings on the namespace will be used.
+
+**Per OnePasswordItem Custom Resource**
+This method allows for managing auto restarts on a given OnePasswordItem custom resource. Auto restarts can by managed by setting the annotation `operator.1password.io/auto_restart` to either `true` or `false` on the desired OnePasswordItem. An example of this is shown below:
+```yaml
+# enabled auto restarts for the OnePasswordItem
+apiVersion: onepassword.com/v1
+kind: OnePasswordItem
+metadata:
+  name: example
+  annotations:
+    operator.1password.io/auto-restart: "true"
+```
+If the value is not set, the auto reset settings on the deployment will be used.
+
+## Development
+
+### Creating a Docker image
+
+To create a local version of the Docker image for testing, use the following `Makefile` target:
+```shell
+make build/local
+```
+
+### Building the Operator binary
+```shell
+make build/binary
+```
+
+The binary will be placed inside a `dist` folder within this repository.
+
+### Running Tests
+
+```shell
+make test
+```
+
+With coverage:
+```shell
+make test/coverage
+```
+
+## Security
+
+1Password requests you practice responsible disclosure if you discover a vulnerability. 
+
+Please file requests via [**BugCrowd**](https://bugcrowd.com/agilebits). 
+
+For information about security practices, please visit our [Security homepage](https://bugcrowd.com/agilebits).

operator/cmd/manager/main.go

@@ -11,16 +11,16 @@ import (
 	"strings"
 	"time"
 
-	"github.com/1Password/onepassword-operator/pkg/controller"
+	"github.com/1Password/onepassword-operator/operator/pkg/controller"
-	op "github.com/1Password/onepassword-operator/pkg/onepassword"
+	op "github.com/1Password/onepassword-operator/operator/pkg/onepassword"
 
 	// Import all Kubernetes client auth plugins (e.g. Azure, GCP, OIDC, etc.)
 
 	_ "k8s.io/client-go/plugin/pkg/client/auth"
 	"k8s.io/client-go/rest"
 
-	"github.com/1Password/onepassword-operator/pkg/apis"
+	"github.com/1Password/onepassword-operator/operator/pkg/apis"
-	"github.com/1Password/onepassword-operator/version"
+	"github.com/1Password/onepassword-operator/operator/version"
 
 	"github.com/1Password/connect-sdk-go/connect"
 

operator/pkg/apis/addtoscheme_onepassword_v1.go

@@ -1,7 +1,7 @@
 package apis
 
 import (
-	v1 "github.com/1Password/onepassword-operator/pkg/apis/onepassword/v1"
+	v1 "github.com/1Password/onepassword-operator/operator/pkg/apis/onepassword/v1"
 )
 
 func init() {

operator/pkg/controller/add_deployment.go

@@ -1,7 +1,7 @@
 package controller
 
 import (
-	"github.com/1Password/onepassword-operator/pkg/controller/deployment"
+	"github.com/1Password/onepassword-operator/operator/pkg/controller/deployment"
 )
 
 func init() {

operator/pkg/controller/add_onepassworditem.go

@@ -1,7 +1,7 @@
 package controller
 
 import (
-	"github.com/1Password/onepassword-operator/pkg/controller/onepassworditem"
+	"github.com/1Password/onepassword-operator/operator/pkg/controller/onepassworditem"
 )
 
 func init() {

operator/pkg/controller/deployment/deployment_controller.go

@@ -3,10 +3,12 @@ package deployment
 import (
 	"context"
 	"fmt"
+	"strings"
 
-	kubeSecrets "github.com/1Password/onepassword-operator/pkg/kubernetessecrets"
+	kubeSecrets "github.com/1Password/onepassword-operator/operator/pkg/kubernetessecrets"
-	op "github.com/1Password/onepassword-operator/pkg/onepassword"
+	"github.com/1Password/onepassword-operator/operator/pkg/onepassword"
-	"github.com/1Password/onepassword-operator/pkg/utils"
+	op "github.com/1Password/onepassword-operator/operator/pkg/onepassword"
+	"github.com/1Password/onepassword-operator/operator/pkg/utils"
 
 	"regexp"
 
@@ -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, annotations, request); err != nil {
 			return reconcile.Result{}, err
 		}
 		return reconcile.Result{}, nil
@@ -187,8 +189,16 @@ 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, annotations map[string]string, request reconcile.Request) error {
 	reqLog := log.WithValues("Request.Namespace", request.Namespace, "Request.Name", request.Name)
+	namespace := deployment.Namespace
+
+	// check if deployment is marked to be injected with secrets via the webhook
+	injectedContainers, injected := annotations[op.ContainerInjectAnnotation]
+	if injected {
+		parsedInjectedContainers := strings.Split(injectedContainers, ",")
+		return onepassword.CreateOnePasswordItemResourceFromDeployment(r.opConnectClient, r.kubeClient, deployment, parsedInjectedContainers)
+	}
 
 	secretName := annotations[op.NameAnnotation]
 	secretLabels := map[string]string(nil)

operator/pkg/controller/deployment/deployment_controller_test.go

@@ -6,8 +6,8 @@ import (
 	"regexp"
 	"testing"
 
-	"github.com/1Password/onepassword-operator/pkg/mocks"
+	"github.com/1Password/onepassword-operator/operator/pkg/mocks"
-	op "github.com/1Password/onepassword-operator/pkg/onepassword"
+	op "github.com/1Password/onepassword-operator/operator/pkg/onepassword"
 
 	"github.com/1Password/connect-sdk-go/onepassword"
 	"github.com/stretchr/testify/assert"

operator/pkg/controller/onepassworditem/onepassworditem_controller.go

@@ -3,11 +3,12 @@ package onepassworditem
 import (
 	"context"
 	"fmt"
-	onepasswordv1 "github.com/1Password/onepassword-operator/pkg/apis/onepassword/v1"
+
-	kubeSecrets "github.com/1Password/onepassword-operator/pkg/kubernetessecrets"
+	onepasswordv1 "github.com/1Password/onepassword-operator/operator/pkg/apis/onepassword/v1"
-	"github.com/1Password/onepassword-operator/pkg/onepassword"
+	kubeSecrets "github.com/1Password/onepassword-operator/operator/pkg/kubernetessecrets"
-	op "github.com/1Password/onepassword-operator/pkg/onepassword"
+	"github.com/1Password/onepassword-operator/operator/pkg/onepassword"
-	"github.com/1Password/onepassword-operator/pkg/utils"
+	op "github.com/1Password/onepassword-operator/operator/pkg/onepassword"
+	"github.com/1Password/onepassword-operator/operator/pkg/utils"
 
 	"github.com/1Password/connect-sdk-go/connect"
 
@@ -147,6 +148,13 @@ func (r *ReconcileOnePasswordItem) HandleOnePasswordItem(resource *onepasswordv1
 	annotations := resource.Annotations
 	autoRestart := annotations[op.RestartDeploymentsAnnotation]
 
+	// do not create kubernetes secret if the OnePasswordItem was generated
+	// due to secret being injected container via webhook
+	_, injectedSecret := annotations[op.InjectedAnnotation]
+	if injectedSecret {
+		return nil
+	}
+
 	item, err := onepassword.GetOnePasswordItemByPath(r.opConnectClient, resource.Spec.ItemPath)
 	if err != nil {
 		return fmt.Errorf("Failed to retrieve item: %v", err)

operator/pkg/controller/onepassworditem/onepassworditem_test.go

@@ -5,10 +5,10 @@ import (
 	"fmt"
 	"testing"
 
-	"github.com/1Password/onepassword-operator/pkg/mocks"
+	"github.com/1Password/onepassword-operator/operator/pkg/mocks"
-	op "github.com/1Password/onepassword-operator/pkg/onepassword"
+	op "github.com/1Password/onepassword-operator/operator/pkg/onepassword"
 
-	onepasswordv1 "github.com/1Password/onepassword-operator/pkg/apis/onepassword/v1"
+	onepasswordv1 "github.com/1Password/onepassword-operator/operator/pkg/apis/onepassword/v1"
 
 	"github.com/1Password/connect-sdk-go/onepassword"
 	"github.com/stretchr/testify/assert"

operator/pkg/kubernetessecrets/kubernetes_secrets_builder.go

@@ -5,15 +5,15 @@ import (
 	"fmt"
 
 	"regexp"
-	"strings"
+
+	"reflect"
 
 	"github.com/1Password/connect-sdk-go/onepassword"
-	"github.com/1Password/onepassword-operator/pkg/utils"
+	"github.com/1Password/onepassword-operator/operator/pkg/utils"
 	corev1 "k8s.io/api/core/v1"
 	"k8s.io/apimachinery/pkg/api/errors"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/apimachinery/pkg/types"
-	"reflect"
 	kubeValidate "k8s.io/apimachinery/pkg/util/validation"
 
 	kubernetesClient "sigs.k8s.io/controller-runtime/pkg/client"
@@ -75,7 +75,7 @@ func CreateKubernetesSecretFromItem(kubeClient kubernetesClient.Client, secretNa
 func BuildKubernetesSecretFromOnePasswordItem(name, namespace string, annotations map[string]string, labels map[string]string, item onepassword.Item) *corev1.Secret {
 	return &corev1.Secret{
 		ObjectMeta: metav1.ObjectMeta{
-			Name:        formatSecretName(name),
+			Name:        utils.FormatSecretName(name),
 			Namespace:   namespace,
 			Annotations: annotations,
 			Labels:      labels,
@@ -95,17 +95,6 @@ func BuildKubernetesSecretData(fields []*onepassword.ItemField) map[string][]byt
 	return secretData
 }
 
-// formatSecretName rewrites a value to be a valid Secret name.
-//
-// The Secret meta.name and data keys must be valid DNS subdomain names
-// (https://kubernetes.io/docs/concepts/configuration/secret/#overview-of-secrets)
-func formatSecretName(value string) string {
-	if errs := kubeValidate.IsDNS1123Subdomain(value); len(errs) == 0 {
-		return value
-	}
-	return createValidSecretName(value)
-}
-
 // formatSecretDataName rewrites a value to be a valid Secret data key.
 //
 // The Secret data keys must consist of alphanumeric numbers, `-`, `_` or `.`
@@ -117,20 +106,6 @@ func formatSecretDataName(value string) string {
 	return createValidSecretDataName(value)
 }
 
-var invalidDNS1123Chars = regexp.MustCompile("[^a-z0-9-.]+")
-
-func createValidSecretName(value string) string {
-	result := strings.ToLower(value)
-	result = invalidDNS1123Chars.ReplaceAllString(result, "-")
-
-	if len(result) > kubeValidate.DNS1123SubdomainMaxLength {
-		result = result[0:kubeValidate.DNS1123SubdomainMaxLength]
-	}
-
-	// first and last character MUST be alphanumeric
-	return strings.Trim(result, "-.")
-}
-
 var invalidDataChars = regexp.MustCompile("[^a-zA-Z0-9-._]+")
 var invalidStartEndChars = regexp.MustCompile("(^[^a-zA-Z0-9-._]+|[^a-zA-Z0-9-._]+$)")
 

operator/pkg/onepassword/annotations.go

@@ -14,6 +14,8 @@ const (
 	VersionAnnotation            = OnepasswordPrefix + "/item-version"
 	RestartAnnotation            = OnepasswordPrefix + "/last-restarted"
 	RestartDeploymentsAnnotation = OnepasswordPrefix + "/auto-restart"
+	ContainerInjectAnnotation    = OnepasswordPrefix + "/inject"
+	InjectedAnnotation           = OnepasswordPrefix + "/injected"
 )
 
 func GetAnnotationsForDeployment(deployment *appsv1.Deployment, regex *regexp.Regexp) (map[string]string, bool) {

operator/pkg/onepassword/containers.go

@@ -1,6 +1,10 @@
 package onepassword
 
-import corev1 "k8s.io/api/core/v1"
+import (
+	onepasswordv1 "github.com/1Password/onepassword-operator/operator/pkg/apis/onepassword/v1"
+	"github.com/1Password/onepassword-operator/operator/pkg/utils"
+	corev1 "k8s.io/api/core/v1"
+)
 
 func AreContainersUsingSecrets(containers []corev1.Container, secrets map[string]*corev1.Secret) bool {
 	for i := 0; i < len(containers); i++ {
@@ -31,3 +35,29 @@ func AppendUpdatedContainerSecrets(containers []corev1.Container, secrets map[st
 	}
 	return updatedDeploymentSecrets
 }
+
+func AreContainersUsingInjectedSecrets(containers []corev1.Container, injectedContainers []string, items map[string]*onepasswordv1.OnePasswordItem) bool {
+	for _, container := range containers {
+		envVariables := container.Env
+
+		// check if container was set to be injected with secrets
+		for _, injectedContainer := range injectedContainers {
+			if injectedContainer != container.Name {
+				continue
+			}
+		}
+
+		// check if any environment variables are using an updated injected secret
+		for _, envVariable := range envVariables {
+			referenceVault, referenceItem, err := ParseReference(envVariable.Value)
+			if err != nil {
+				continue
+			}
+			_, itemFound := items[utils.BuildInjectedOnePasswordItemName(referenceVault, referenceItem)]
+			if itemFound {
+				return true
+			}
+		}
+	}
+	return false
+}

operator/pkg/onepassword/deployments.go

@@ -1,6 +1,9 @@
 package onepassword
 
 import (
+	"strings"
+
+	onepasswordv1 "github.com/1Password/onepassword-operator/operator/pkg/apis/onepassword/v1"
 	appsv1 "k8s.io/api/apps/v1"
 	corev1 "k8s.io/api/core/v1"
 )
@@ -24,3 +27,14 @@ func GetUpdatedSecretsForDeployment(deployment *appsv1.Deployment, secrets map[s
 
 	return updatedSecretsForDeployment
 }
+
+func IsDeploymentUsingInjectedSecrets(deployment *appsv1.Deployment, items map[string]*onepasswordv1.OnePasswordItem) bool {
+	containers := deployment.Spec.Template.Spec.Containers
+	containers = append(containers, deployment.Spec.Template.Spec.InitContainers...)
+	injectedContainers, enabled := deployment.Spec.Template.Annotations[ContainerInjectAnnotation]
+	if !enabled {
+		return false
+	}
+	parsedInjectedContainers := strings.Split(injectedContainers, ",")
+	return AreContainersUsingInjectedSecrets(containers, parsedInjectedContainers, items)
+}

operator/pkg/onepassword/items.go

@@ -11,6 +11,16 @@ import (
 
 var logger = logf.Log.WithName("retrieve_item")
 
+const secretReferencePrefix = "op://"
+
+type InvalidOPFormatError struct {
+	Reference string
+}
+
+func (e *InvalidOPFormatError) Error() string {
+	return fmt.Sprintf("Invalid secret reference : %s. Secret references should start with op://", e.Reference)
+}
+
 func GetOnePasswordItemByPath(opConnectClient connect.Client, path string) (*onepassword.Item, error) {
 	vaultValue, itemValue, err := ParseVaultAndItemFromPath(path)
 	if err != nil {
@@ -33,6 +43,30 @@ func GetOnePasswordItemByPath(opConnectClient connect.Client, path string) (*one
 	return item, nil
 }
 
+func ParseReference(reference string) (string, string, error) {
+	if !strings.HasPrefix(reference, secretReferencePrefix) {
+		return "", "", &InvalidOPFormatError{Reference: reference}
+	}
+	path := strings.TrimPrefix(reference, secretReferencePrefix)
+
+	splitPath := strings.Split(path, "/")
+	if len(splitPath) != 3 {
+		return "", "", fmt.Errorf("Invalid secret reference : %s. Secret references should match op://<vault>/<item>/<field>", reference)
+	}
+
+	vault := splitPath[0]
+	if vault == "" {
+		return "", "", fmt.Errorf("Invalid secret reference : %s. Vault can't be empty.", reference)
+	}
+
+	item := splitPath[1]
+	if item == "" {
+		return "", "", fmt.Errorf("Invalid secret reference : %s. Item can't be empty.", reference)
+	}
+
+	return vault, item, nil
+}
+
 func ParseVaultAndItemFromPath(path string) (string, string, error) {
 	splitPath := strings.Split(path, "/")
 	if len(splitPath) == 4 && splitPath[0] == "vaults" && splitPath[2] == "items" {

operator/pkg/onepassword/onepassword_item.go

@@ -0,0 +1,95 @@
+package onepassword
+
+import (
+	"context"
+	"errors"
+	"fmt"
+
+	"github.com/1Password/connect-sdk-go/connect"
+	onepasswordv1 "github.com/1Password/onepassword-operator/operator/pkg/apis/onepassword/v1"
+	"github.com/1Password/onepassword-operator/operator/pkg/utils"
+	k8sErrors "k8s.io/apimachinery/pkg/api/errors"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+	"k8s.io/apimachinery/pkg/types"
+
+	appsv1 "k8s.io/api/apps/v1"
+	corev1 "k8s.io/api/core/v1"
+	kubernetesClient "sigs.k8s.io/controller-runtime/pkg/client"
+)
+
+func CreateOnePasswordItemResourceFromDeployment(opClient connect.Client, kubeClient kubernetesClient.Client, deployment *appsv1.Deployment, injectedContainers []string) error {
+	containers := deployment.Spec.Template.Spec.Containers
+	containers = append(containers, deployment.Spec.Template.Spec.InitContainers...)
+	for _, container := range containers {
+		// check if container is listed is one of the containers
+		// set to have injected secrets
+		for _, injectedContainer := range injectedContainers {
+			if injectedContainer != container.Name {
+				continue
+			}
+			// create a one password item custom resource to track updates for injected secrets
+			err := CreateOnePasswordCRSecretsFromContainer(opClient, kubeClient, container, deployment.Namespace)
+			if err != nil {
+				return err
+			}
+		}
+	}
+	return nil
+}
+
+func CreateOnePasswordCRSecretsFromContainer(opClient connect.Client, kubeClient kubernetesClient.Client, container corev1.Container, namespace string) error {
+	for _, env := range container.Env {
+		// if value is not of format op://<vault>/<item>/<field> then ignore
+		vault, item, err := ParseReference(env.Value)
+		if err != nil {
+			var ev *InvalidOPFormatError
+			if !errors.As(err, &ev) {
+				return err
+			}
+			continue
+		}
+		// create a one password item custom resource to track updates for injected secrets
+		err = CreateOnePasswordCRSecretFromReference(opClient, kubeClient, vault, item, namespace)
+		if err != nil {
+			return err
+		}
+	}
+	return nil
+}
+
+func CreateOnePasswordCRSecretFromReference(opClient connect.Client, kubeClient kubernetesClient.Client, vault, item, namespace string) error {
+
+	retrievedItem, err := GetOnePasswordItemByPath(opClient, fmt.Sprintf("vaults/%s/items/%s", vault, item))
+	if err != nil {
+		return fmt.Errorf("Failed to retrieve item: %v", err)
+	}
+
+	name := utils.BuildInjectedOnePasswordItemName(vault, item)
+	onepassworditem := BuildOnePasswordItemCRFromPath(vault, item, name, namespace, fmt.Sprint(retrievedItem.Version))
+
+	currentOnepassworditem := &onepasswordv1.OnePasswordItem{}
+	err = kubeClient.Get(context.Background(), types.NamespacedName{Name: onepassworditem.Name, Namespace: onepassworditem.Namespace}, currentOnepassworditem)
+	if k8sErrors.IsNotFound(err) {
+		log.Info(fmt.Sprintf("Creating OnePasswordItem CR %v at namespace '%v'", onepassworditem.Name, onepassworditem.Namespace))
+		return kubeClient.Create(context.Background(), onepassworditem)
+	} else if err != nil {
+		return err
+	}
+	return nil
+}
+
+func BuildOnePasswordItemCRFromPath(vault, item, name, namespace, version string) *onepasswordv1.OnePasswordItem {
+	return &onepasswordv1.OnePasswordItem{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      name,
+			Namespace: namespace,
+			Annotations: map[string]string{
+				InjectedAnnotation: "true",
+				VersionAnnotation:  version,
+			},
+		},
+		Spec: onepasswordv1.OnePasswordItemSpec{
+			ItemPath: fmt.Sprintf("vaults/%s/items/%s", vault, item),
+		},
+	}
+}

operator/pkg/onepassword/onepassword_item_test.go

@@ -0,0 +1,234 @@
+package onepassword
+
+import (
+	"context"
+	"fmt"
+	"strings"
+	"testing"
+
+	"github.com/1Password/onepassword-operator/operator/pkg/mocks"
+
+	"github.com/1Password/connect-sdk-go/onepassword"
+	onepasswordv1 "github.com/1Password/onepassword-operator/operator/pkg/apis/onepassword/v1"
+	"github.com/stretchr/testify/assert"
+	appsv1 "k8s.io/api/apps/v1"
+	corev1 "k8s.io/api/core/v1"
+	errors2 "k8s.io/apimachinery/pkg/api/errors"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+	"k8s.io/apimachinery/pkg/runtime"
+	"k8s.io/apimachinery/pkg/types"
+	"k8s.io/kubectl/pkg/scheme"
+	"sigs.k8s.io/controller-runtime/pkg/client/fake"
+)
+
+type onepassworditemInjections struct {
+	testName           string
+	existingDeployment *appsv1.Deployment
+	existingNamespace  *corev1.Namespace
+	expectedError      error
+	expectedEvents     []string
+	opItem             map[string]string
+	expectedOPItem     *onepasswordv1.OnePasswordItem
+}
+
+var onepassworditemTests = []onepassworditemInjections{
+	{
+		testName:          "Try to Create OnePasswordItem with container with valid op reference",
+		existingNamespace: defaultNamespace,
+		existingDeployment: &appsv1.Deployment{
+			TypeMeta: metav1.TypeMeta{
+				Kind:       deploymentKind,
+				APIVersion: deploymentAPIVersion,
+			},
+			ObjectMeta: metav1.ObjectMeta{
+				Name:      name,
+				Namespace: namespace,
+			},
+			Spec: appsv1.DeploymentSpec{
+				Template: corev1.PodTemplateSpec{
+					ObjectMeta: metav1.ObjectMeta{
+						Name:      name,
+						Namespace: namespace,
+						Annotations: map[string]string{
+							ContainerInjectAnnotation: "test-app",
+						},
+					},
+					Spec: corev1.PodSpec{
+						Containers: []corev1.Container{
+							{
+								Name: "test-app",
+								Env: []corev1.EnvVar{
+									{
+										Name:  name,
+										Value: fmt.Sprintf("op://%s/%s/test", vaultId, itemId),
+									},
+								},
+							},
+						},
+					},
+				},
+			},
+		},
+		expectedError: nil,
+		opItem: map[string]string{
+			userKey: username,
+			passKey: password,
+		},
+		expectedOPItem: &onepasswordv1.OnePasswordItem{
+			TypeMeta: metav1.TypeMeta{
+				Kind:       "OnePasswordItem",
+				APIVersion: "onepassword.com/v1",
+			},
+			ObjectMeta: metav1.ObjectMeta{
+				Name:      injectedOnePasswordItemName,
+				Namespace: namespace,
+				Annotations: map[string]string{
+					InjectedAnnotation: "true",
+					VersionAnnotation:  "old",
+				},
+			},
+			Spec: onepasswordv1.OnePasswordItemSpec{
+				ItemPath: itemPath,
+			},
+		},
+	},
+	{
+		testName:          "Container with no op:// reference does not create OnePasswordItem",
+		existingNamespace: defaultNamespace,
+		existingDeployment: &appsv1.Deployment{
+			TypeMeta: metav1.TypeMeta{
+				Kind:       deploymentKind,
+				APIVersion: deploymentAPIVersion,
+			},
+			ObjectMeta: metav1.ObjectMeta{
+				Name:      name,
+				Namespace: namespace,
+			},
+			Spec: appsv1.DeploymentSpec{
+				Template: corev1.PodTemplateSpec{
+					ObjectMeta: metav1.ObjectMeta{
+						Name:      name,
+						Namespace: namespace,
+						Annotations: map[string]string{
+							ContainerInjectAnnotation: "test-app",
+						},
+					},
+					Spec: corev1.PodSpec{
+						Containers: []corev1.Container{
+							{
+								Name: "test-app",
+								Env: []corev1.EnvVar{
+									{
+										Name:  name,
+										Value: fmt.Sprintf("some value"),
+									},
+								},
+							},
+						},
+					},
+				},
+			},
+		},
+		expectedError: nil,
+		opItem: map[string]string{
+			userKey: username,
+			passKey: password,
+		},
+		expectedOPItem: nil,
+	},
+	{
+		testName:          "Container with op:// reference missing vault and item does not create OnePasswordItem and returns error",
+		existingNamespace: defaultNamespace,
+		existingDeployment: &appsv1.Deployment{
+			TypeMeta: metav1.TypeMeta{
+				Kind:       deploymentKind,
+				APIVersion: deploymentAPIVersion,
+			},
+			ObjectMeta: metav1.ObjectMeta{
+				Name:      name,
+				Namespace: namespace,
+			},
+			Spec: appsv1.DeploymentSpec{
+				Template: corev1.PodTemplateSpec{
+					ObjectMeta: metav1.ObjectMeta{
+						Name:      name,
+						Namespace: namespace,
+						Annotations: map[string]string{
+							ContainerInjectAnnotation: "test-app",
+						},
+					},
+					Spec: corev1.PodSpec{
+						Containers: []corev1.Container{
+							{
+								Name: "test-app",
+								Env: []corev1.EnvVar{
+									{
+										Name:  name,
+										Value: fmt.Sprintf("op://"),
+									},
+								},
+							},
+						},
+					},
+				},
+			},
+		},
+		expectedError: fmt.Errorf("Invalid secret reference : %s. Secret references should match op://<vault>/<item>/<field>", "op://"),
+		opItem: map[string]string{
+			userKey: username,
+			passKey: password,
+		},
+		expectedOPItem: nil,
+	},
+}
+
+func TestOnePasswordItemSecretInjected(t *testing.T) {
+	for _, testData := range onepassworditemTests {
+		t.Run(testData.testName, func(t *testing.T) {
+
+			// Register operator types with the runtime scheme.
+			s := scheme.Scheme
+			s.AddKnownTypes(appsv1.SchemeGroupVersion, &onepasswordv1.OnePasswordItem{}, &onepasswordv1.OnePasswordItemList{}, &appsv1.Deployment{})
+
+			// Objects to track in the fake client.
+			objs := []runtime.Object{
+				testData.existingDeployment,
+				testData.existingNamespace,
+			}
+
+			// Create a fake client to mock API calls.
+			cl := fake.NewFakeClientWithScheme(s, objs...)
+
+			opConnectClient := &mocks.TestClient{}
+			mocks.GetGetItemFunc = func(uuid string, vaultUUID string) (*onepassword.Item, error) {
+
+				item := onepassword.Item{}
+				item.Fields = generateFields(testData.opItem["username"], testData.opItem["password"])
+				item.Version = itemVersion
+				item.Vault.ID = vaultUUID
+				item.ID = uuid
+				return &item, nil
+			}
+
+			injectedContainers := testData.existingDeployment.Spec.Template.ObjectMeta.Annotations[ContainerInjectAnnotation]
+			parsedInjectedContainers := strings.Split(injectedContainers, ",")
+			err := CreateOnePasswordItemResourceFromDeployment(opConnectClient, cl, testData.existingDeployment, parsedInjectedContainers)
+
+			assert.Equal(t, testData.expectedError, err)
+
+			// Check if Secret has been created and has the correct data
+			opItemCR := &onepasswordv1.OnePasswordItem{}
+			err = cl.Get(context.TODO(), types.NamespacedName{Name: injectedOnePasswordItemName, Namespace: namespace}, opItemCR)
+
+			if testData.expectedOPItem == nil {
+				assert.Error(t, err)
+				assert.True(t, errors2.IsNotFound(err))
+			} else {
+				assert.Equal(t, testData.expectedOPItem.Spec.ItemPath, opItemCR.Spec.ItemPath)
+				assert.Equal(t, testData.expectedOPItem.Name, opItemCR.Name)
+				assert.Equal(t, testData.expectedOPItem.Annotations[InjectedAnnotation], opItemCR.Annotations[InjectedAnnotation])
+			}
+
+		})
+	}
+}

operator/pkg/onepassword/secret_update_handler.go

@@ -5,8 +5,9 @@ import (
 	"fmt"
 	"time"
 
-	kubeSecrets "github.com/1Password/onepassword-operator/pkg/kubernetessecrets"
+	onepasswordv1 "github.com/1Password/onepassword-operator/operator/pkg/apis/onepassword/v1"
-	"github.com/1Password/onepassword-operator/pkg/utils"
+	kubeSecrets "github.com/1Password/onepassword-operator/operator/pkg/kubernetessecrets"
+	"github.com/1Password/onepassword-operator/operator/pkg/utils"
 
 	"github.com/1Password/connect-sdk-go/connect"
 	"github.com/1Password/connect-sdk-go/onepassword"
@@ -41,12 +42,17 @@ func (h *SecretUpdateHandler) UpdateKubernetesSecretsTask() error {
 		return err
 	}
 
-	return h.restartDeploymentsWithUpdatedSecrets(updatedKubernetesSecrets)
+	updatedInjectedSecrets, err := h.updateInjectedSecrets()
+	if err != nil {
+		return err
 	}
 
-func (h *SecretUpdateHandler) restartDeploymentsWithUpdatedSecrets(updatedSecretsByNamespace map[string]map[string]*corev1.Secret) error {
+	return h.restartDeploymentsWithUpdatedSecrets(updatedKubernetesSecrets, updatedInjectedSecrets)
-	// No secrets to update. Exit
+}
-	if len(updatedSecretsByNamespace) == 0 || updatedSecretsByNamespace == nil {
+
+func (h *SecretUpdateHandler) restartDeploymentsWithUpdatedSecrets(updatedSecretsByNamespace map[string]map[string]*corev1.Secret, updatedInjectedSecretsByNamespace map[string]map[string]*onepasswordv1.OnePasswordItem) error {
+
+	if len(updatedSecretsByNamespace) == 0 && len(updatedInjectedSecretsByNamespace) == 0 {
 		return nil
 	}
 
@@ -63,6 +69,7 @@ func (h *SecretUpdateHandler) restartDeploymentsWithUpdatedSecrets(updatedSecret
 
 	setForAutoRestartByNamespaceMap, err := h.getIsSetForAutoRestartByNamespaceMap()
 	if err != nil {
+		log.Error(err, "Error determining which namespaces allow restarts")
 		return err
 	}
 
@@ -70,16 +77,23 @@ func (h *SecretUpdateHandler) restartDeploymentsWithUpdatedSecrets(updatedSecret
 		deployment := &deployments.Items[i]
 		updatedSecrets := updatedSecretsByNamespace[deployment.Namespace]
 
+		// check if deployment is using one of the updated secrets
 		updatedDeploymentSecrets := GetUpdatedSecretsForDeployment(deployment, updatedSecrets)
-		if len(updatedDeploymentSecrets) == 0 {
+		if len(updatedDeploymentSecrets) != 0 {
-			continue
-		}
 			for _, secret := range updatedDeploymentSecrets {
 				if isSecretSetForAutoRestart(secret, deployment, setForAutoRestartByNamespaceMap) {
 					h.restartDeployment(deployment)
 					continue
 				}
 			}
+		}
+
+		// check if the deployment is using one of the updated injected secrets
+		updatedInjection := IsDeploymentUsingInjectedSecrets(deployment, updatedInjectedSecretsByNamespace[deployment.Namespace])
+		if updatedInjection && isDeploymentSetForAutoRestart(deployment, setForAutoRestartByNamespaceMap) {
+			h.restartDeployment(deployment)
+			continue
+		}
 
 		log.Info(fmt.Sprintf("Deployment %q at namespace %q is up to date", deployment.GetName(), deployment.Namespace))
 
@@ -89,9 +103,10 @@ 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{
+	if deployment.Spec.Template.Annotations == nil {
-		RestartAnnotation: time.Now().String(),
+		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")
@@ -142,6 +157,52 @@ func (h *SecretUpdateHandler) updateKubernetesSecrets() (map[string]map[string]*
 	return updatedSecrets, nil
 }
 
+func (h *SecretUpdateHandler) updateInjectedSecrets() (map[string]map[string]*onepasswordv1.OnePasswordItem, error) {
+	// fetch all onepassworditems
+	onepasswordItems := &onepasswordv1.OnePasswordItemList{}
+	err := h.client.List(context.Background(), onepasswordItems)
+	if err != nil {
+		log.Error(err, "Failed to list OnePasswordItems")
+		return nil, err
+	}
+
+	updatedItems := map[string]map[string]*onepasswordv1.OnePasswordItem{}
+	for _, item := range onepasswordItems.Items {
+
+		// if onepassworditem was not generated by injecting a secret into a deployment then ignore
+		_, injected := item.Annotations[InjectedAnnotation]
+		if !injected {
+			continue
+		}
+
+		itemPath := item.Spec.ItemPath
+		currentVersion := item.Annotations[VersionAnnotation]
+		if len(itemPath) == 0 || len(currentVersion) == 0 {
+			continue
+		}
+
+		storedItem, err := GetOnePasswordItemByPath(h.opConnectClient, itemPath)
+		if err != nil {
+			return nil, fmt.Errorf("Failed to retrieve item: %v", err)
+		}
+
+		itemVersion := fmt.Sprint(storedItem.Version)
+		if currentVersion != itemVersion {
+			item.Annotations[VersionAnnotation] = itemVersion
+			h.client.Update(context.Background(), &item)
+			if isItemLockedForForcedRestarts(storedItem) {
+				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 OnePasswordItem secret or a rolling restart.", item.Name))
+				continue
+			}
+			if updatedItems[item.Namespace] == nil {
+				updatedItems[item.Namespace] = make(map[string]*onepasswordv1.OnePasswordItem)
+			}
+			updatedItems[item.Namespace][item.Name] = &item
+		}
+	}
+	return updatedItems, nil
+}
+
 func isItemLockedForForcedRestarts(item *onepassword.Item) bool {
 	tags := item.Tags
 	for i := 0; i < len(tags); i++ {
@@ -178,7 +239,7 @@ func (h *SecretUpdateHandler) getIsSetForAutoRestartByNamespaceMap() (map[string
 
 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
+	//If annotation for auto restarts for deployment is not set. Check for the annotation on its deployment
 	if restartDeployment == "" {
 		return isDeploymentSetForAutoRestart(deployment, setForAutoRestartByNamespace)
 	}

operator/pkg/onepassword/secret_update_handler_test.go

@@ -5,9 +5,10 @@ import (
 	"fmt"
 	"testing"
 
-	"github.com/1Password/onepassword-operator/pkg/mocks"
+	"github.com/1Password/onepassword-operator/operator/pkg/mocks"
 
 	"github.com/1Password/connect-sdk-go/onepassword"
+	onepasswordv1 "github.com/1Password/onepassword-operator/operator/pkg/apis/onepassword/v1"
 	"github.com/stretchr/testify/assert"
 	appsv1 "k8s.io/api/apps/v1"
 	corev1 "k8s.io/api/core/v1"
@@ -31,12 +32,14 @@ const (
 	userKey                     = "username"
 	passKey                     = "password"
 	itemVersion                 = 123
+	injectedOnePasswordItemName = "injectedsecret-" + vaultId + "-" + itemId
 )
 
 type testUpdateSecretTask struct {
 	testName                 string
 	existingDeployment       *appsv1.Deployment
 	existingNamespace        *corev1.Namespace
+	existingOnePasswordItem  *onepasswordv1.OnePasswordItem
 	existingSecret           *corev1.Secret
 	expectedError            error
 	expectedResultSecret     *corev1.Secret
@@ -755,6 +758,123 @@ var tests = []testUpdateSecretTask{
 		expectedRestart:          true,
 		globalAutoRestartEnabled: false,
 	},
+	{
+		testName:          "OP item has new version. Secret needs update. Deployment is restarted based on injected secrets in containers",
+		existingNamespace: defaultNamespace,
+		existingDeployment: &appsv1.Deployment{
+			TypeMeta: metav1.TypeMeta{
+				Kind:       deploymentKind,
+				APIVersion: deploymentAPIVersion,
+			},
+			ObjectMeta: metav1.ObjectMeta{
+				Name:      name,
+				Namespace: namespace,
+			},
+			Spec: appsv1.DeploymentSpec{
+				Template: corev1.PodTemplateSpec{
+					ObjectMeta: metav1.ObjectMeta{
+						Name:      name,
+						Namespace: namespace,
+						Annotations: map[string]string{
+							ContainerInjectAnnotation: "test-app",
+						},
+					},
+					Spec: corev1.PodSpec{
+						Containers: []corev1.Container{
+							{
+								Name: "test-app",
+								Env: []corev1.EnvVar{
+									{
+										Name:  name,
+										Value: fmt.Sprintf("op://%s/%s/test", vaultId, itemId),
+									},
+								},
+							},
+						},
+					},
+				},
+			},
+		},
+		existingOnePasswordItem: &onepasswordv1.OnePasswordItem{
+			TypeMeta: metav1.TypeMeta{
+				Kind:       "OnePasswordItem",
+				APIVersion: "onepassword.com/v1",
+			},
+			ObjectMeta: metav1.ObjectMeta{
+				Name:      injectedOnePasswordItemName,
+				Namespace: namespace,
+				Annotations: map[string]string{
+					InjectedAnnotation: "true",
+					VersionAnnotation:  "old",
+				},
+			},
+			Spec: onepasswordv1.OnePasswordItemSpec{
+				ItemPath: itemPath,
+			},
+		},
+		expectedError: nil,
+		opItem: map[string]string{
+			userKey: username,
+			passKey: password,
+		},
+		expectedRestart:          true,
+		globalAutoRestartEnabled: true,
+	},
+	{
+		testName:          "OP item has new version. Secret needs update. Deployment does not have a inject annotation",
+		existingNamespace: defaultNamespace,
+		existingDeployment: &appsv1.Deployment{
+			TypeMeta: metav1.TypeMeta{
+				Kind:       deploymentKind,
+				APIVersion: deploymentAPIVersion,
+			},
+			ObjectMeta: metav1.ObjectMeta{
+				Name:      name,
+				Namespace: namespace,
+			},
+			Spec: appsv1.DeploymentSpec{
+				Template: corev1.PodTemplateSpec{
+					Spec: corev1.PodSpec{
+						Containers: []corev1.Container{
+							{
+								Name: "test-app",
+								Env: []corev1.EnvVar{
+									{
+										Name:  name,
+										Value: fmt.Sprintf("op://%s/%s/test", vaultId, itemId),
+									},
+								},
+							},
+						},
+					},
+				},
+			},
+		},
+		existingOnePasswordItem: &onepasswordv1.OnePasswordItem{
+			TypeMeta: metav1.TypeMeta{
+				Kind:       "OnePasswordItem",
+				APIVersion: "onepassword.com/v1",
+			},
+			ObjectMeta: metav1.ObjectMeta{
+				Name:      fmt.Sprintf("%s-%s", vaultId, itemId),
+				Namespace: namespace,
+				Annotations: map[string]string{
+					InjectedAnnotation: "true",
+					VersionAnnotation:  "old",
+				},
+			},
+			Spec: onepasswordv1.OnePasswordItemSpec{
+				ItemPath: itemPath,
+			},
+		},
+		expectedError: nil,
+		opItem: map[string]string{
+			userKey: username,
+			passKey: password,
+		},
+		expectedRestart:          false,
+		globalAutoRestartEnabled: true,
+	},
 }
 
 func TestUpdateSecretHandler(t *testing.T) {
@@ -763,7 +883,7 @@ func TestUpdateSecretHandler(t *testing.T) {
 
 			// Register operator types with the runtime scheme.
 			s := scheme.Scheme
-			s.AddKnownTypes(appsv1.SchemeGroupVersion, testData.existingDeployment)
+			s.AddKnownTypes(appsv1.SchemeGroupVersion, &onepasswordv1.OnePasswordItem{}, &onepasswordv1.OnePasswordItemList{}, &appsv1.Deployment{})
 
 			// Objects to track in the fake client.
 			objs := []runtime.Object{
@@ -775,6 +895,10 @@ func TestUpdateSecretHandler(t *testing.T) {
 				objs = append(objs, testData.existingSecret)
 			}
 
+			if testData.existingOnePasswordItem != nil {
+				objs = append(objs, testData.existingOnePasswordItem)
+			}
+
 			// Create a fake client to mock API calls.
 			cl := fake.NewFakeClientWithScheme(s, objs...)
 
@@ -825,9 +949,9 @@ func TestUpdateSecretHandler(t *testing.T) {
 
 			_, ok := deployment.Spec.Template.Annotations[RestartAnnotation]
 			if ok {
-				assert.True(t, testData.expectedRestart, "Expected deployment to restart but it did not")
+				assert.True(t, testData.expectedRestart, "Deployment was restarted but should not have been.")
 			} else {
-				assert.False(t, testData.expectedRestart, "Deployment was restarted but should not have been.")
+				assert.False(t, testData.expectedRestart, "Expected deployment to restart but it did not")
 			}
 		})
 	}

operator/pkg/utils/string.go

@@ -0,0 +1,66 @@
+package utils
+
+import (
+	"fmt"
+	"regexp"
+	"strconv"
+	"strings"
+
+	kubeValidate "k8s.io/apimachinery/pkg/util/validation"
+)
+
+var invalidDNS1123Chars = regexp.MustCompile("[^a-z0-9-.]+")
+
+func ContainsString(slice []string, s string) bool {
+	for _, item := range slice {
+		if item == s {
+			return true
+		}
+	}
+	return false
+}
+
+func RemoveString(slice []string, s string) (result []string) {
+	for _, item := range slice {
+		if item == s {
+			continue
+		}
+		result = append(result, item)
+	}
+	return
+}
+
+func StringToBool(str string) (bool, error) {
+	restartDeploymentBool, err := strconv.ParseBool(strings.ToLower(str))
+	if err != nil {
+		return false, err
+	}
+	return restartDeploymentBool, nil
+}
+
+// formatSecretName rewrites a value to be a valid Secret name.
+//
+// The Secret meta.name and data keys must be valid DNS subdomain names
+// (https://kubernetes.io/docs/concepts/configuration/secret/#overview-of-secrets)
+func FormatSecretName(value string) string {
+	if errs := kubeValidate.IsDNS1123Subdomain(value); len(errs) == 0 {
+		return value
+	}
+	return CreateValidSecretName(value)
+}
+
+func CreateValidSecretName(value string) string {
+	result := strings.ToLower(value)
+	result = invalidDNS1123Chars.ReplaceAllString(result, "-")
+
+	if len(result) > kubeValidate.DNS1123SubdomainMaxLength {
+		result = result[0:kubeValidate.DNS1123SubdomainMaxLength]
+	}
+
+	// first and last character MUST be alphanumeric
+	return strings.Trim(result, "-.")
+}
+
+func BuildInjectedOnePasswordItemName(vaultId, injectedId string) string {
+	return FormatSecretName(fmt.Sprintf("injectedsecret-%s-%s", vaultId, injectedId))
+}

pkg/utils/string.go

@@ -1,33 +0,0 @@
-package utils
-
-import (
-	"strconv"
-	"strings"
-)
-
-func ContainsString(slice []string, s string) bool {
-	for _, item := range slice {
-		if item == s {
-			return true
-		}
-	}
-	return false
-}
-
-func RemoveString(slice []string, s string) (result []string) {
-	for _, item := range slice {
-		if item == s {
-			continue
-		}
-		result = append(result, item)
-	}
-	return
-}
-
-func StringToBool(str string) (bool, error) {
-	restartDeploymentBool, err := strconv.ParseBool(strings.ToLower(str))
-	if err != nil {
-		return false, err
-	}
-	return restartDeploymentBool, nil
-}