diff --git a/.github/workflows/bump-latest-cdk8s-plus-library.yml b/.github/workflows/bump-latest-cdk8s-plus-library.yml
index 65338851d4..3fd702acc4 100644
--- a/.github/workflows/bump-latest-cdk8s-plus-library.yml
+++ b/.github/workflows/bump-latest-cdk8s-plus-library.yml
@@ -42,20 +42,40 @@ jobs:
         run: |-
           echo httpStatus="$(curl -sL -w "%{http_code}
           " "https://www.npmjs.com/package/cdk8s-plus-${{steps.k8s-latest-version.outputs.latestVersion}}" -o /dev/null)" >> $GITHUB_OUTPUT
-  generate-new-k8s-spec:
+  configure-testing-mode:
     needs: check-latest-k8s-release
     runs-on: ubuntu-latest
     permissions:
       contents: read
       pull-requests: write
-    env:
-      testingMode: "true"
+    outputs:
+      testingMode: ${{ steps.set-testing-mode-var.outputs.testingMode }}
+      labels: ${{ steps.set-auto-approve-label.outputs.labels }}
     if: needs.check-latest-k8s-release.outputs.httpStatus != 200
     steps:
       - name: Checkout
         uses: actions/checkout@v2
-      - name: Set testingMode env variable
+      - name: Set testingMode environment variable
+        id: set-testing-mode-var
         run: bash src/testModeSet.sh ${{ github.event.inputs.testingMode }}
+      - name: Set auto-approve label for PR
+        id: set-auto-approve-label
+        env:
+          GITHUB_TOKEN: ${{ secrets.PROJEN_GITHUB_TOKEN }}
+        run: if [${{steps.set-testing-mode-var.outputs.testingMode}} = "true"];then echo labels="auto-approve" >> $GITHUB_OUTPUT;fi
+        continue-on-error: false
+  generate-new-k8s-spec:
+    needs:
+      - check-latest-k8s-release
+      - configure-testing-mode
+    runs-on: ubuntu-latest
+    permissions:
+      contents: read
+      pull-requests: write
+    if: needs.check-latest-k8s-release.outputs.httpStatus != 200
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v2
       - name: Setup Node.js
         uses: actions/setup-node@v2
         with:
@@ -67,12 +87,6 @@ jobs:
           GITHUB_TOKEN: ${{ secrets.PROJEN_GITHUB_TOKEN }}
         run: ${{ github.workspace }}/tools/import-spec.sh 1.${{ needs.check-latest-k8s-release.outputs.latestVersion }}.0
         continue-on-error: false
-      - name: Set auto-approve label for PR if in testing mode
-        id: set-auto-approve-label
-        env:
-          GITHUB_TOKEN: ${{ secrets.PROJEN_GITHUB_TOKEN }}
-        run: if [$testingMode = "true"];then echo labels="auto-approve" >> $GITHUB_OUTPUT;fi
-        continue-on-error: false
       - name: Create Pull Request
         id: create-pr
         uses: peter-evans/create-pull-request@v4
@@ -90,7 +104,7 @@ jobs:
             *Automatically created by projen via the "create-pull-request" workflow*
           branch: github-actions/generate-k8s-spec-${{ needs.check-latest-k8s-release.outputs.latestVersion }}${{ steps.set-auto-approve-label.outputs.labels }}
           title: "chore: v${{ needs.check-latest-k8s-release.outputs.latestVersion }}${{ steps.set-auto-approve-label.outputs.labels }} kubernetes-spec"
-          labels: ${{ steps.set-auto-approve-label.outputs.labels }}
+          labels: ${{ needs.configure-testing-mode.set-auto-approve-label.outputs.labels }}
           body: |-
             This PR adds the v${{ needs.check-latest-k8s-release.outputs.latestVersion }} Kubernetes spec. This is required in order for us to add a new version to cdk8s-plus. See details in [workflow run].
 
@@ -103,7 +117,9 @@ jobs:
           committer: github-actions <github-actions@github.com>
           signoff: true
   add-backport-label:
-    needs: check-latest-k8s-release
+    needs:
+      - check-latest-k8s-release
+      - configure-testing-mode
     runs-on: ubuntu-latest
     permissions:
       contents: read
@@ -123,6 +139,7 @@ jobs:
     needs:
       - check-latest-k8s-release
       - generate-new-k8s-spec
+      - configure-testing-mode
     runs-on: ubuntu-latest
     permissions:
       contents: read
@@ -151,7 +168,7 @@ jobs:
       - name: Import the new k8s spec from the prerequisite step
         run: yarn run import
       - name: Disable publishing
-        run: npx projen disable-publishing
+        run: if [${{ needs.configure-testing-mode.outputs.testingMode }}"true"];then npx projen disable-publishing;fi
       - name: Test package json output
         run: cat package.json
       - name: Let projen update the remaining files
@@ -177,6 +194,7 @@ jobs:
     needs:
       - check-latest-k8s-release
       - create-new-plus-branch
+      - configure-testing-mode
     runs-on: ubuntu-latest
     permissions:
       contents: read
@@ -220,6 +238,7 @@ jobs:
             *Automatically created by projen via the "create-pull-request" workflow*
           branch: github-actions/website-update-${{ needs.check-latest-k8s-release.outputs.latestVersion }}
           title: "chore(website): cdk8s-plus-${{ needs.check-latest-k8s-release.outputs.latestVersion }}"
+          labels: ${{ needs.configure-testing-mode.set-auto-approve-label.outputs.labels }}
           body: |-
             This PR updates the website with the latest version of cdk8s-plus. See details in [workflow run].
 
@@ -235,6 +254,7 @@ jobs:
     needs:
       - check-latest-k8s-release
       - update-cdk8s-website
+      - configure-testing-mode
     runs-on: ubuntu-latest
     permissions:
       contents: read
@@ -266,6 +286,7 @@ jobs:
             *Automatically created by projen via the "create-pull-request" workflow*
           branch: github-actions/cdk-ops-k8s-upgrade-${{ needs.check-latest-k8s-release.outputs.latestVersion }}
           title: "chore: updating latest cdk8s-plus version to v${{ needs.check-latest-k8s-release.outputs.latestVersion }}"
+          labels: ${{ needs.configure-testing-mode.set-auto-approve-label.outputs.labels }}
           body: |-
             This PR updates the reference to of the latest cdk8s-plus version. See details in [workflow run].
 
diff --git a/src/k8s-automation.ts b/src/k8s-automation.ts
index 51dad20dac..8456c4f90a 100644
--- a/src/k8s-automation.ts
+++ b/src/k8s-automation.ts
@@ -40,7 +40,7 @@ export class K8sVersionUpgradeAutomation extends Component {
 
     const runsOn = ['ubuntu-latest'];
 
-    // PART 0: Check Latest Kubernetes Version Online
+    // PART 0: Check Latest Kubernetes Version Online and configure Testing Mode
 
     const checkLatestVersion: workflows.Job = {
       runsOn: runsOn,
@@ -93,9 +93,8 @@ export class K8sVersionUpgradeAutomation extends Component {
     };
 
     workflow.addJob('check-latest-k8s-release', checkLatestVersion);
-    // PART 1: Prerequisite
 
-    const generateK8sSpecJob: workflows.Job = {
+    const configureTestingMode: workflows.Job = {
       runsOn: runsOn,
       permissions: {
         contents: workflows.JobPermission.READ,
@@ -103,8 +102,15 @@ export class K8sVersionUpgradeAutomation extends Component {
       },
       needs: ['check-latest-k8s-release'],
       if: 'needs.check-latest-k8s-release.outputs.httpStatus != 200',
-      env: {
-        testingMode: 'true',
+      outputs: {
+        testingMode: {
+          stepId: 'set-testing-mode-var',
+          outputName: 'testingMode',
+        },
+        labels: {
+          stepId: 'set-auto-approve-label',
+          outputName: 'labels',
+        },
       },
       steps: [
         {
@@ -112,9 +118,37 @@ export class K8sVersionUpgradeAutomation extends Component {
           uses: 'actions/checkout@v2',
         },
         {
-          name: 'Set testingMode env variable',
+          name: 'Set testingMode environment variable',
+          id: 'set-testing-mode-var',
           run: 'bash src/testModeSet.sh ${{ github.event.inputs.testingMode }}',
         },
+        {
+          name: 'Set auto-approve label for PR',
+          id: 'set-auto-approve-label',
+          run: 'if [${{steps.set-testing-mode-var.outputs.testingMode}} = "true"];then echo labels="auto-approve" >> $GITHUB_OUTPUT;fi',
+          env: { GITHUB_TOKEN: '${{ secrets.PROJEN_GITHUB_TOKEN }}' },
+          continueOnError: false,
+        },
+      ],
+    };
+
+    workflow.addJob('configure-testing-mode', configureTestingMode);
+
+    // PART 1: Prerequisite
+
+    const generateK8sSpecJob: workflows.Job = {
+      runsOn: runsOn,
+      permissions: {
+        contents: workflows.JobPermission.READ,
+        pullRequests: workflows.JobPermission.WRITE,
+      },
+      needs: ['check-latest-k8s-release', 'configure-testing-mode'],
+      if: 'needs.check-latest-k8s-release.outputs.httpStatus != 200',
+      steps: [
+        {
+          name: 'Checkout',
+          uses: 'actions/checkout@v2',
+        },
         {
           name: 'Setup Node.js',
           uses: 'actions/setup-node@v2',
@@ -130,26 +164,13 @@ export class K8sVersionUpgradeAutomation extends Component {
           env: { GITHUB_TOKEN: '${{ secrets.PROJEN_GITHUB_TOKEN }}' },
           continueOnError: false,
         },
-        {
-          name: 'Set auto-approve label for PR if in testing mode',
-          id: 'set-auto-approve-label',
-          // if: '!(${{ github.event_name }} == "push")',
-          // run: 'echo labels="bug" >> $GITHUB_OUTPUT;',
-          //${{ github.event.inputs.testingMode }}
-          // run: 'bash src/testingModeScript.sh ${{ github.event_name }} ${{ github.event.inputs.testingMode }}',
-          run: 'if [$testingMode = "true"];then echo labels="auto-approve" >> $GITHUB_OUTPUT;fi',
-          // if: 'github.event.inputs.testingMode == false',
-          // run: 'echo labels="auto-approve" >> $GITHUB_OUTPUT',
-          env: { GITHUB_TOKEN: '${{ secrets.PROJEN_GITHUB_TOKEN }}' },
-          continueOnError: false,
-        },
         ...WorkflowActions.createPullRequest({
           workflowName: 'create-pull-request',
           pullRequestTitle: 'chore: v${{ needs.check-latest-k8s-release.outputs.latestVersion }}${{ steps.set-auto-approve-label.outputs.labels }} kubernetes-spec',
           pullRequestDescription: 'This PR adds the v${{ needs.check-latest-k8s-release.outputs.latestVersion }} Kubernetes spec. This is required in order for us to add a new version to cdk8s-plus.',
           branchName: 'github-actions/generate-k8s-spec-${{ needs.check-latest-k8s-release.outputs.latestVersion }}${{ steps.set-auto-approve-label.outputs.labels }}',
           labels: [
-            '${{ steps.set-auto-approve-label.outputs.labels }}',
+            '${{ needs.configure-testing-mode.set-auto-approve-label.outputs.labels }}',
           ],
           credentials: GithubCredentials.fromPersonalAccessToken(),
         }),
@@ -164,7 +185,7 @@ export class K8sVersionUpgradeAutomation extends Component {
         contents: workflows.JobPermission.READ,
         pullRequests: workflows.JobPermission.WRITE,
       },
-      needs: ['check-latest-k8s-release'],
+      needs: ['check-latest-k8s-release', 'configure-testing-mode'],
       if: 'needs.check-latest-k8s-release.outputs.httpStatus != 200',
       steps: [
         {
@@ -195,7 +216,7 @@ export class K8sVersionUpgradeAutomation extends Component {
         contents: workflows.JobPermission.READ,
         pullRequests: workflows.JobPermission.WRITE,
       },
-      needs: ['check-latest-k8s-release', 'generate-new-k8s-spec'],
+      needs: ['check-latest-k8s-release', 'generate-new-k8s-spec', 'configure-testing-mode'],
       steps: [
         {
           name: 'Checkout',
@@ -230,11 +251,8 @@ export class K8sVersionUpgradeAutomation extends Component {
           run: 'yarn run import',
         },
         {
-          // TESTING MODE: Disable publishing. Delete / comment this out before running it for real.
-          // if: '${{ github.event.inputs.testingMode }} == true',
-          // name: 'Disable publishing if testingMode is true',
           name: 'Disable publishing',
-          run: 'npx projen disable-publishing',
+          run: 'if [${{ needs.configure-testing-mode.outputs.testingMode }}"true"];then npx projen disable-publishing;fi',
         },
         {
           name: 'Test package json output',
@@ -282,7 +300,7 @@ export class K8sVersionUpgradeAutomation extends Component {
         pullRequests: workflows.JobPermission.WRITE,
       },
       // add the cdk8s-plus update job to needs when it's done:
-      needs: ['check-latest-k8s-release', 'create-new-plus-branch'],
+      needs: ['check-latest-k8s-release', 'create-new-plus-branch', 'configure-testing-mode'],
       if: 'needs.check-latest-k8s-release.outputs.httpStatus != 200',
       steps: [
         {
@@ -315,14 +333,6 @@ export class K8sVersionUpgradeAutomation extends Component {
           env: { GITHUB_TOKEN: '${{ secrets.PROJEN_GITHUB_TOKEN }}' },
           continueOnError: false,
         },
-        // {
-        //   name: 'Set auto-approve label for PR if in testing mode',
-        //   id: 'set-auto-approve-label',
-        //   if: '${{ github.event.inputs.testingMode }} == false',
-        //   run: 'echo labels="auto-approve" >> $GITHUB_OUTPUT',
-        //   env: { GITHUB_TOKEN: '${{ secrets.PROJEN_GITHUB_TOKEN }}' },
-        //   continueOnError: false,
-        // },
         ...WorkflowActions.createPullRequest({
           workflowName: 'create-pull-request',
           pullRequestTitle: 'chore(website): cdk8s-plus-${{ needs.check-latest-k8s-release.outputs.latestVersion }}',
@@ -330,7 +340,7 @@ export class K8sVersionUpgradeAutomation extends Component {
           branchName: 'github-actions/website-update-${{ needs.check-latest-k8s-release.outputs.latestVersion }}',
           credentials: GithubCredentials.fromPersonalAccessToken(),
           labels: [
-            // '${{ steps.set-auto-approve-label.outputs.labels }}',
+            '${{ needs.configure-testing-mode.set-auto-approve-label.outputs.labels }}',
           ],
         }),
       ],
@@ -338,13 +348,15 @@ export class K8sVersionUpgradeAutomation extends Component {
 
     workflow.addJob('update-cdk8s-website', updateCdk8s);
 
+    // PART 4: Update CDK Ops
+
     const updateCdkOps: workflows.Job = {
       runsOn: runsOn,
       permissions: {
         contents: workflows.JobPermission.READ,
         pullRequests: workflows.JobPermission.WRITE,
       },
-      needs: ['check-latest-k8s-release', 'update-cdk8s-website'],
+      needs: ['check-latest-k8s-release', 'update-cdk8s-website', 'configure-testing-mode'],
       steps: [
         {
           name: 'Checkout',
@@ -360,21 +372,13 @@ export class K8sVersionUpgradeAutomation extends Component {
           env: { GITHUB_TOKEN: '${{ secrets.PROJEN_GITHUB_TOKEN }}' },
           continueOnError: false,
         },
-        // {
-        //   name: 'Set auto-approve label for PR if in testing mode',
-        //   id: 'set-auto-approve-label',
-        //   if: '${{ github.event.inputs.testingMode }} == false',
-        //   run: 'echo labels="auto-approve" >> $GITHUB_OUTPUT',
-        //   env: { GITHUB_TOKEN: '${{ secrets.PROJEN_GITHUB_TOKEN }}' },
-        //   continueOnError: false,
-        // },
         ...WorkflowActions.createPullRequest({
           workflowName: 'create-pull-request',
           pullRequestTitle: 'chore: updating latest cdk8s-plus version to v${{ needs.check-latest-k8s-release.outputs.latestVersion }}',
           pullRequestDescription: 'This PR updates the reference to of the latest cdk8s-plus version',
           branchName: 'github-actions/cdk-ops-k8s-upgrade-${{ needs.check-latest-k8s-release.outputs.latestVersion }}',
           labels: [
-          //   // '${{ steps.set-auto-approve-label.outputs.labels }}',
+            '${{ needs.configure-testing-mode.set-auto-approve-label.outputs.labels }}',
           ],
           credentials: GithubCredentials.fromPersonalAccessToken(),
         }),
diff --git a/src/testModeSet.sh b/src/testModeSet.sh
index 19185f444b..a8a35f71fa 100644
--- a/src/testModeSet.sh
+++ b/src/testModeSet.sh
@@ -1,5 +1,4 @@
 #!/bin/bash
 
 TESTING_MODE_INPUT="$1"
-echo testingMode=${TESTING_MODE_INPUT:-"true"} >> $GITHUB_ENV
-# echo testingMode=${TESTING_MODE_INPUT:-"true"}
\ No newline at end of file
+echo testingMode=${TESTING_MODE_INPUT:-"true"} >> >> $GITHUB_OUTPUT