diff --git a/.github/workflows/update-licenses.yml b/.github/workflows/update-licenses.yml
new file mode 100644
index 0000000000..344120e1dc
--- /dev/null
+++ b/.github/workflows/update-licenses.yml
@@ -0,0 +1,34 @@
+name: Update Licenses
+
+on:
+  # Every day at 2am
+  schedule:
+    - cron: "0 2 * * *"
+  # Manual trigger
+  workflow_dispatch:
+
+jobs:
+  build:
+    runs-on: ubuntu-latest
+
+    steps:
+    - uses: actions/checkout@v2
+
+    - name: Set up Python
+      uses: actions/setup-python@v2
+      with:
+        python-version: 3.8
+    - name: Install dependencies
+      run: |
+        python -m pip install --upgrade pip
+        pip install -r requirements.txt
+    - name: Update list
+      run: python scripts/update_licenses.py
+      env:
+        GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+
+    - name: Commit changes
+      uses: stefanzweifel/git-auto-commit-action@v4.9.1
+      with:
+        commit_message: Update Licenses
+        file_pattern: cookiecutter.json {{cookiecutter.project_slug}}/licenses/*.txt
diff --git a/scripts/update_licenses.py b/scripts/update_licenses.py
new file mode 100644
index 0000000000..457471b612
--- /dev/null
+++ b/scripts/update_licenses.py
@@ -0,0 +1,35 @@
+import json
+import os
+from pathlib import Path
+from github import Github
+
+CURRENT_FILE = Path(__file__)
+ROOT = CURRENT_FILE.parents[1]
+GITHUB_TOKEN = os.getenv("GITHUB_TOKEN", None)
+
+
+def main() -> None:
+    """
+    Script entry point.
+    """
+    repo = Github(login_or_token=GITHUB_TOKEN).get_repo("github/choosealicense.com")
+    license_dir = ROOT / "{{cookiecutter.project_slug}}" / "licenses"
+    titles = []
+    for file in repo.get_contents("_licenses", "gh-pages"):
+        content = file.decoded_content.decode(file.encoding)
+        titles.append(content.split("\n", maxsplit=2)[1].replace("title: ", ""))
+        (license_dir / file.name).write_text(content)
+    # Put "Not open source" at front so people know it's an option
+    update_cookiecutter(["Not open source"] + sorted(titles))
+
+
+def update_cookiecutter(titles: list):
+    with open("cookiecutter.json") as f:
+        data = json.load(f)
+    data["open_source_license"] = titles
+    with open("cookiecutter.json", "wt") as f:
+        json.dump(data, f, indent=2)
+
+
+if __name__ == "__main__":
+    main()