diff --git a/.github/workflows/regen-examples-and-docs.yml b/.github/workflows/regen-examples-and-docs.yml
new file mode 100644
index 00000000..081fb4fc
--- /dev/null
+++ b/.github/workflows/regen-examples-and-docs.yml
@@ -0,0 +1,59 @@
+name: Regenerate examples and docs
+
+on:
+  cron: "0 */12 * * *"
+  push:
+    branches:
+      - main
+    paths:
+      - '.github/workflows/regen-examples-and-docs.yml'
+      - 'src/**'
+      - 'scripts/**'
+  workflow_dispatch:
+
+env:
+  PIP_DISABLE_PIP_VERSION_CHECK: 1
+
+jobs:
+  regen_examples_and_docs:
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/checkout@v3
+      - uses: actions/setup-python@v4
+        with:
+          cache: "pip"
+          cache-dependency-path: |
+            requirements-dev.txt
+            pyproject.toml
+          python-version: "3.10"
+      - name: Install wheel
+        run: pip install "wheel<1"
+      - name: Install requirements
+        run: |
+          pip install -r requirements-dev.txt
+          pip install -e .[everything]
+      - name: Regenerate examples and docs
+        run: |
+          python scripts/regenerate_examples_and_docs.py
+          git commit -a -m "Automated regeneration of examples and docs"
+      - name: Deploy docs
+        run: mkdocs gh-deploy --force
+
+  create-issue-on-failure:
+    name: Create an issue if the automated regeneration failed
+    runs-on: ubuntu-latest
+    needs: [regen_examples_and_docs]
+    if: ${{ github.repository == 'AlexWaygood/typeshed-stats' && always() && github.event_name != 'workflow_dispatch' && (needs.regen_examples_and_docs.result == 'failure') }}
+    permissions:
+      issues: write
+    steps:
+      - uses: actions/github-script@v6
+        with:
+          github-token: ${{ secrets.GITHUB_TOKEN }}
+          script: |
+            await github.rest.issues.create({
+              owner: "AlexWaygood",
+              repo: "typeshed-stats",
+              title: `Automated regeneration of examples failed on ${new Date().toDateString()}`,
+              body: "Runs are listed here: https://github.com/AlexWaygood/typeshed-stats/actions/workflows/regen-examples-and-docs.yml",
+            })