diff --git a/.github/workflows/release-k8-operator-helm.yml b/.github/workflows/release-k8-operator-helm.yml
new file mode 100644
index 000000000..f3731fb46
--- /dev/null
+++ b/.github/workflows/release-k8-operator-helm.yml
@@ -0,0 +1,27 @@
+name: Release K8 Operator Helm Chart
+on:
+    workflow_dispatch:
+
+jobs:
+    release-helm:
+        name: Release Helm Chart
+        runs-on: ubuntu-latest
+        steps:
+            - name: Checkout
+              uses: actions/checkout@v2
+
+            - name: Install Helm
+              uses: azure/setup-helm@v3
+              with:
+                  version: v3.10.0
+
+            - name: Install python
+              uses: actions/setup-python@v4
+
+            - name: Install Cloudsmith CLI
+              run: pip install --upgrade cloudsmith-cli
+
+            - name: Build and push helm package to CloudSmith
+              run: cd helm-charts && sh upload-k8s-operator-cloudsmith.sh
+              env:
+                  CLOUDSMITH_API_KEY: ${{ secrets.CLOUDSMITH_API_KEY }}
diff --git a/.github/workflows/release_docker_k8_operator.yaml b/.github/workflows/release_docker_k8_operator.yaml
index 162cc9dc0..4af62df1c 100644
--- a/.github/workflows/release_docker_k8_operator.yaml
+++ b/.github/workflows/release_docker_k8_operator.yaml
@@ -1,52 +1,103 @@
-name: Release image + Helm chart K8s Operator
+name: Release K8 Operator Docker Image
 on:
-  push:
-    tags:
-      - "infisical-k8-operator/v*.*.*"
+    push:
+        tags:
+            - "infisical-k8-operator/v*.*.*"
 
 jobs:
-  release:
-    runs-on: ubuntu-latest
-    steps:
-      - name: Extract version from tag
-        id: extract_version
-        run: echo "::set-output name=version::${GITHUB_REF_NAME#infisical-k8-operator/}"
-      - uses: actions/checkout@v2
+    release-image:
+        name: Generate Helm Chart PR
+        runs-on: ubuntu-latest
+        outputs:
+            pr_number: ${{ steps.create-pr.outputs.pull-request-number }}
+        steps:
+            - name: Extract version from tag
+              id: extract_version
+              run: echo "::set-output name=version::${GITHUB_REF_NAME#infisical-k8-operator/}"
 
-      - name: 🔧 Set up QEMU
-        uses: docker/setup-qemu-action@v1
+            - name: Checkout code
+              uses: actions/checkout@v2
 
-      - name: 🔧 Set up Docker Buildx
-        uses: docker/setup-buildx-action@v1
+            # Dependency for helm generation
+            - name: Install Helm
+              uses: azure/setup-helm@v3
+              with:
+                  version: v3.10.0
 
-      - name: 🐋 Login to Docker Hub
-        uses: docker/login-action@v1
-        with:
-          username: ${{ secrets.DOCKERHUB_USERNAME }}
-          password: ${{ secrets.DOCKERHUB_TOKEN }}
+            # Dependency for helm generation
+            - name: Install Go
+              uses: actions/setup-go@v4
+              with:
+                  go-version: 1.21
 
-      - name: Build and push
-        id: docker_build
-        uses: docker/build-push-action@v2
-        with:
-          context: k8-operator
-          push: true
-          platforms: linux/amd64,linux/arm64
-          tags: |
-            infisical/kubernetes-operator:latest
-            infisical/kubernetes-operator:${{ steps.extract_version.outputs.version }}
+            # Install binaries for helm generation
+            - name: Install dependencies
+              working-directory: k8-operator
+              run: |
+                  make helmify
+                  make kustomize
+                  make controller-gen
 
-      - name: Checkout
-        uses: actions/checkout@v2
-      - name: Install Helm
-        uses: azure/setup-helm@v3
-        with:
-          version: v3.10.0
-      - name: Install python
-        uses: actions/setup-python@v4
-      - name: Install Cloudsmith CLI
-        run: pip install --upgrade cloudsmith-cli
-      - name: Build and push helm package to Cloudsmith
-        run: cd helm-charts && sh upload-k8s-operator-cloudsmith.sh
-        env:
-          CLOUDSMITH_API_KEY: ${{ secrets.CLOUDSMITH_API_KEY }}
+            - name: Generate Helm Chart
+              working-directory: k8-operator
+              run: make helm
+
+            - name: Update Helm Chart Version
+              run: ./k8-operator/scripts/update-version.sh ${{ steps.extract_version.outputs.version }}
+
+            - name: Debug - Check file changes
+              run: |
+                  echo "Current git status:"
+                  git status
+                  echo ""
+                  echo "Modified files:"
+                  git diff --name-only
+
+                  # If there is no diff, exit with error. Version should always be changed, so if there is no diff, something is wrong and we should exit.
+                  if [ -z "$(git diff --name-only)" ]; then
+                    echo "No helm changes or version changes. Invalid release detected, Exiting."
+                    exit 1
+                  fi
+
+            - name: Create Helm Chart PR
+              id: create-pr
+              uses: peter-evans/create-pull-request@v5
+              with:
+                  token: ${{ secrets.GITHUB_TOKEN }}
+                  commit-message: "Update Helm chart to version ${{ steps.extract_version.outputs.version }}"
+                  committer: GitHub <noreply@github.com>
+                  author: ${{ github.actor }} <${{ github.actor }}@users.noreply.github.com>
+                  branch: helm-update-${{ steps.extract_version.outputs.version }}
+                  delete-branch: true
+                  title: "Update Helm chart to version ${{ steps.extract_version.outputs.version }}"
+                  body: |
+                      This PR updates the Helm chart to version `${{ steps.extract_version.outputs.version }}`.
+                      Additionally the helm chart has been updated to match the latest operator code changes.
+
+                      Associated Release Workflow: https://github.com/${{ github.repository }}/actions/runs/${{ github.run_id }}
+
+                      Once you have approved this PR, you can trigger the helm release workflow manually.
+                  base: main
+
+            - name: 🔧 Set up QEMU
+              uses: docker/setup-qemu-action@v1
+
+            - name: 🔧 Set up Docker Buildx
+              uses: docker/setup-buildx-action@v1
+
+            - name: 🐋 Login to Docker Hub
+              uses: docker/login-action@v1
+              with:
+                  username: ${{ secrets.DOCKERHUB_USERNAME }}
+                  password: ${{ secrets.DOCKERHUB_TOKEN }}
+
+            - name: Build and push
+              id: docker_build
+              uses: docker/build-push-action@v2
+              with:
+                  context: k8-operator
+                  push: true
+                  platforms: linux/amd64,linux/arm64
+                  tags: |
+                      infisical/kubernetes-operator:latest
+                      infisical/kubernetes-operator:${{ steps.extract_version.outputs.version }}