diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 7043ab9..aadd60a 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -14,6 +14,56 @@ on:
     - cron: "0 9 * * 1"
 
 jobs:
+  engines:
+    name: Engines - ${{ matrix.platform.name }} - ${{ matrix.node-version }}
+    if: github.repository_owner == 'npm'
+    strategy:
+      fail-fast: false
+      matrix:
+        platform:
+          - name: Linux
+            os: ubuntu-latest
+            shell: bash
+        node-version:
+          - 14.17.0
+          - 16.13.0
+          - 18.0.0
+    runs-on: ${{ matrix.platform.os }}
+    defaults:
+      run:
+        shell: ${{ matrix.platform.shell }}
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v3
+      - name: Setup Git User
+        run: |
+          git config --global user.email "npm-cli+bot@github.com"
+          git config --global user.name "npm CLI robot"
+      - name: Setup Node
+        uses: actions/setup-node@v3
+        with:
+          node-version: ${{ matrix.node-version }}
+      - name: Update Windows npm
+        # node 12 and 14 ship with npm@6, which is known to fail when updating itself in windows
+        if: matrix.platform.os == 'windows-latest' && (startsWith(matrix.node-version, '12.') || startsWith(matrix.node-version, '14.'))
+        run: |
+          curl -sO https://registry.npmjs.org/npm/-/npm-7.5.4.tgz
+          tar xf npm-7.5.4.tgz
+          cd package
+          node lib/npm.js install --no-fund --no-audit -g ..\npm-7.5.4.tgz
+          cd ..
+          rmdir /s /q package
+      - name: Install npm@7
+        if: startsWith(matrix.node-version, '10.')
+        run: npm i --prefer-online --no-fund --no-audit -g npm@7
+      - name: Install npm@latest
+        if: ${{ !startsWith(matrix.node-version, '10.') }}
+        run: npm i --prefer-online --no-fund --no-audit -g npm@latest
+      - name: npm Version
+        run: npm -v
+      - name: Install Dependencies
+        run: npm i --ignore-scripts --no-audit --no-fund --engines-strict
+
   lint:
     name: Lint
     if: github.repository_owner == 'npm'
diff --git a/.github/workflows/post-dependabot.yml b/.github/workflows/post-dependabot.yml
index 98acf69..e854e12 100644
--- a/.github/workflows/post-dependabot.yml
+++ b/.github/workflows/post-dependabot.yml
@@ -19,7 +19,7 @@ jobs:
       - name: Checkout
         uses: actions/checkout@v3
         with:
-          ref: ${{ github.event.pull_request.head_ref }}
+          ref: ${{ github.ref_name }}
       - name: Setup Git User
         run: |
           git config --global user.email "npm-cli+bot@github.com"
@@ -46,10 +46,13 @@ jobs:
         if: contains(steps.metadata.outputs.dependency-names, '@npmcli/template-oss')
         id: flags
         run: |
-          if [[ "${{ steps.metadata.outputs.directory }}" == "/" ]]; then
+          dependabot_dir="${{ steps.metadata.outputs.directory }}"
+          if [[ "$dependabot_dir" == "/" ]]; then
             echo "::set-output name=workspace::-iwr"
           else
-            echo "::set-output name=workspace::-w ${{ steps.metadata.outputs.directory }}"
+            # strip leading slash from directory so it works as a
+            # a path to the workspace flag
+            echo "::set-output name=workspace::-w ${dependabot_dir#/}"
           fi
 
       - name: Apply Changes
@@ -60,6 +63,15 @@ jobs:
           if [[ `git status --porcelain` ]]; then
             echo "::set-output name=changes::true"
           fi
+          # This only sets the conventional commit prefix. This workflow can't reliably determine
+          # what the breaking change is though. If a BREAKING CHANGE message is required then
+          # this PR check will fail and the commit will be amended with stafftools
+          if [[ "${{ steps.dependabot-metadata.outputs.update-type }}" == "version-update:semver-major" ]]; then
+            prefix='feat!'
+          else
+            prefix='chore!'
+          fi
+          echo "::set-output name=message::$prefix: postinstall for dependabot template-oss PR"
 
       # This step will fail if template-oss has made any workflow updates. It is impossible
       # for a workflow to update other workflows. In the case it does fail, we continue
@@ -71,21 +83,39 @@ jobs:
         env:
           GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
         run: |
-          git commit -am "chore: postinstall for dependabot template-oss PR"
+          git commit -am "${{ steps.apply.outputs.message }}"
           git push
 
+      # If the previous step failed, then reset the commit and remove any workflow changes
+      # and attempt to commit and push again. This is helpful because we will have a commit
+      # with the correct prefix that we can then --amend with @npmcli/stafftools later.
       - name: Push All Changes Except Workflows
-        if: steps.push.outcome == 'failure'
+        if: steps.apply.outputs.changes && steps.push-all.outcome == 'failure'
         env:
           GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
         run: |
           git reset HEAD~
           git checkout HEAD -- .github/workflows/
           git clean -fd .github/workflows/
-          git commit -am "chore: postinstall for dependabot template-oss PR"
+          git commit -am "${{ steps.apply.outputs.message }}"
           git push
 
+      # Check if all the necessary template-oss changes were applied. Since we continued
+      # on errors in one of the previous steps, this check will fail if our follow up
+      # only applied a portion of the changes and we need to followup manually.
+      #
+      # Note that this used to run `lint` and `postlint` but that will fail this action
+      # if we've also shipped any linting changes separate from template-oss. We do
+      # linting in another action, so we want to fail this one only if there are
+      # template-oss changes that could not be applied.
       - name: Check Changes
         if: steps.apply.outputs.changes
         run: |
           npm exec --offline ${{ steps.flags.outputs.workspace }} -- template-oss-check
+
+      - name: Fail on Breaking Change
+        if: steps.apply.outputs.changes && startsWith(steps.apply.outputs.message, 'feat!')
+        run: |
+          echo "This PR has a breaking change. Run 'npx -p @npmcli/stafftools gh template-oss-fix'"
+          echo "for more information on how to fix this with a BREAKING CHANGE footer."
+          exit 1
diff --git a/package.json b/package.json
index de40fab..6486526 100644
--- a/package.json
+++ b/package.json
@@ -43,6 +43,6 @@
   "author": "GitHub Inc.",
   "templateOSS": {
     "//@npmcli/template-oss": "This file is partially managed by @npmcli/template-oss. Edits may be overwritten.",
-    "version": "4.3.2"
+    "version": "4.4.4"
   }
 }