diff --git a/.github/workflows/check.yml b/.github/workflows/check.yml
new file mode 100644
index 00000000..27745a45
--- /dev/null
+++ b/.github/workflows/check.yml
@@ -0,0 +1,49 @@
+name: Check Scripts
+
+on:
+  push:
+  pull_request:
+
+jobs:
+  correctly-generated:
+    name: "are correctly generated"
+    runs-on: ubuntu-latest
+    steps:
+    - uses: actions/checkout@v2
+    - uses: actions/setup-python@v2
+    - run: pip install nox
+
+    - run: nox -s generate
+    - name: Check regenerated scripts vs what is generated by automation.
+      run: git diff --exit-code
+
+  work-as-advertised:
+    name: "work as advertised"
+    runs-on: ubuntu-latest
+    steps:
+    - uses: actions/checkout@v2
+    - uses: actions/setup-python@v2
+    - run: pip install nox
+
+    # Install supported Python versions
+    - uses: actions/setup-python@v2
+      with:
+        python-version: 2.7
+    - uses: actions/setup-python@v2
+      with:
+        python-version: 3.5
+    - uses: actions/setup-python@v2
+      with:
+        python-version: 3.6
+    - uses: actions/setup-python@v2
+      with:
+        python-version: 3.7
+    - uses: actions/setup-python@v2
+      with:
+        python-version: 3.8
+    - uses: actions/setup-python@v2
+      with:
+        python-version: 3.9
+
+    # Check that the scripts work.
+    - run: nox -s check
diff --git a/.github/workflows/tests.yml b/.github/workflows/tests.yml
deleted file mode 100644
index 80ac12af..00000000
--- a/.github/workflows/tests.yml
+++ /dev/null
@@ -1,29 +0,0 @@
-name: Tests
-
-on:
-  push:
-  pull_request:
-
-jobs:
-  tests:
-    name: ${{ matrix.os }} / ${{ matrix.python }}
-    runs-on: ${{ matrix.os }}-latest
-    strategy:
-      matrix:
-        os: [Ubuntu, Windows]
-        python: ['2.7', '3.7']
-    steps:
-    - uses: actions/checkout@master
-
-    - uses: actions/setup-python@v2
-    - run: pip install nox
-
-    - uses: actions/setup-python@v2
-      with:
-        python-version: ${{ matrix.python }}
-    - name: nox + Windows + Python 2.7 workaround
-      # This is in PATH, so nox resolves to it - but then subsequent steps fail
-      run: rm C:/ProgramData/Chocolatey/bin/python2.7.exe
-      if: matrix.os == 'Windows' && matrix.python == '2.7'
-
-    - run: nox -s tests-${{ matrix.python }}
diff --git a/.gitignore b/.gitignore
index 23276e9b..5ef39967 100644
--- a/.gitignore
+++ b/.gitignore
@@ -1,3 +1,4 @@
 /.nox/
 /venv/
 __pycache__/
+.web_cache/
diff --git a/README.md b/README.md
new file mode 100644
index 00000000..58a87c0a
--- /dev/null
+++ b/README.md
@@ -0,0 +1,72 @@
+# get-pip.py
+
+`get-pip.py` is a bootstrapping script that enables users to install pip,
+setuptools, and wheel in Python environments that don't already have them. You
+should not directly reference the files located in this repository and instead
+use the versions located at <https://bootstrap.pypa.io/>.
+
+## Usage
+
+```console
+$ curl -sSL https://bootstrap.pypa.io/get-pip.py -o get-pip.py
+$ python get-pip.py
+```
+
+Upon execution, `get-pip.py` will install `pip`, `setuptools` and `wheel` in
+the current Python environment.
+
+It is possible to provide additional arguments to the underlying script. These
+are passed through to the underlying `pip install` command, and can thus be
+used to constraint the versions of the packages, or to pass other pip options
+such as `--no-index`.
+
+```console
+$ python get-pip.py "pip < 21.0" "setuptools < 50.0" "wheel < 1.0"
+$ python get-pip.py --no-index --find-links=/local/copies
+```
+
+### get-pip.py options
+
+This script also has it's own options, which control which packages it will
+install.
+
+- `--no-setuptools`: do not attempt to install `setuptools`.
+- `--no-wheel`: do not attempt to install `wheel`.
+
+## Development
+
+You need to have a [`nox`](https://nox.readthedocs.io/) available on the CLI.
+
+### How it works
+
+`get-pip.py` bundles a copy of pip with a tiny amount of glue code. This glue
+code comes from the `templates/` directory.
+
+### Updating after a pip release
+
+If you just made a pip release, run `nox -s update-for-release -- <version>`.
+This session will handle all the script updates (by running `generate`), commit
+the changes and tag the commit.
+
+IMPORTANT: Check that the correct files got modified before pushing. The session
+will pause to let you do this.
+
+### Generating the scripts
+
+Run `nox -s generate`.
+
+## Discussion
+
+If you run into bugs, you can file them in our [issue tracker].
+
+You can also join `#pypa` or `#pypa-dev` on Freenode to ask questions or
+get involved.
+
+[issue tracker]: https://github.com/pypa/get-pip/issues
+
+## Code of Conduct
+
+Everyone interacting in the get-pip project's codebases, issue trackers, chat
+rooms, and mailing lists is expected to follow the [PSF Code of Conduct].
+
+[PSF Code of Conduct]: https://github.com/pypa/.github/blob/main/CODE_OF_CONDUCT.md
diff --git a/README.rst b/README.rst
deleted file mode 100644
index d58210bc..00000000
--- a/README.rst
+++ /dev/null
@@ -1,86 +0,0 @@
-get-pip.py
-==========
-
-``get-pip.py`` is a bootstrapping script that enables users to install pip,
-setuptools, and wheel in Python environments that don't already have them. You
-should not directly reference the files located in this repository and instead
-use the versions located at https://bootstrap.pypa.io/.
-
-
-Usage
------
-
-.. code-block:: console
-
-    $ curl -sSL https://bootstrap.pypa.io/get-pip.py -o get-pip.py
-    $ python get-pip.py
-
-Upon execution, ``get-pip.py`` will install ``pip``, ``setuptools`` and
-``wheel`` in the current Python environment.
-
-It is possible to provide additional arguments to the underlying script. These
-are passed through to the underlying `pip install` command, and can thus be
-used to constraint the versions of the packages, or to pass other pip options
-such as ``--no-index``.
-
-.. code-block:: console
-
-    $ python get-pip.py "pip < 21.0" "setuptools < 50.0" "wheel < 1.0"
-    $ python get-pip.py --no-index --find-links=/local/copies
-
-get-pip.py options
-^^^^^^^^^^^^^^^^^^
-
-This script also has it's own options, which control which packages it will
-install.
-
-``--no-setuptools``
-    If set, do not attempt to install ``setuptools``.
-
-``--no-wheel``
-    If set, do not attempt to install ``wheel``.
-
-
-Development
------------
-
-Most of the work of ``get-pip.py`` comes from the copy of pip that is bundled
-inside of it. However, there is a tiny bit of glue code located inside of
-``template.py`` to enable ``get-pip.py`` to actually work.
-
-Install the dependencies from ``requirements.txt`` to get setup with the repo.
-You may want to perform something like:
-
-.. code-block:: console
-
-    $ python3 -m venv venv
-    $ source venv/bin/activate
-    $ pip install -r requirements.txt
-
-Any pull request should include regenerated files, which can be generated by
-running:
-
-.. code-block:: console
-
-    $ invoke generate
-
-
-Discussion
-----------
-
-If you run into bugs, you can file them in our `issue tracker`_.
-
-You can also join ``#pypa`` or ``#pypa-dev`` on Freenode to ask questions or
-get involved.
-
-
-.. _`issue tracker`: https://github.com/pypa/get-pip/issues
-
-
-Code of Conduct
----------------
-
-Everyone interacting in the get-pip project's codebases, issue trackers, chat
-rooms, and mailing lists is expected to follow the `PSF Code of Conduct`_.
-
-.. _PSF Code of Conduct: https://github.com/pypa/.github/blob/main/CODE_OF_CONDUCT.md
diff --git a/noxfile.py b/noxfile.py
index b2081f45..a542f74d 100644
--- a/noxfile.py
+++ b/noxfile.py
@@ -1,9 +1,94 @@
 import os
+import textwrap
+from pathlib import Path
 
 import nox
 
+nox.options.sessions = ["check", "generate"]
 
-@nox.session(python=['2.7', '3.7'])
-def tests(session):
-    session.install('pytest')
-    session.run('pytest')
+
+# Keep versions in sync with .github/workflows/check.yml
+@nox.session(
+    python=["2.6", "2.7", "3.2", "3.3", "3.4", "3.5", "3.6", "3.7", "3.8", "3.9"]
+)
+def check(session):
+    """Ensure that get-pip.py for various Python versions, works on that version."""
+
+    # Find the appropriate get-pip.py file
+    public = Path(".")
+    locations = [
+        public / session.python / "get-pip.py",
+        public / "get-pip.py",
+    ]
+    for location in locations:
+        if location.exists():
+            break
+    else:  # AKA nobreak
+        raise RuntimeError("There is no public get-pip.py")
+
+    # Get rid of provided-by-nox pip
+    session.run("python", "-m", "pip", "uninstall", "pip", "--yes")
+    # Run the get-pip.py file
+    session.run("python", str(location))
+    # Ensure that pip is installed
+    session.run("python", "-m", "pip", "--version")
+    session.run("pip", "--version")
+
+
+@nox.session
+def generate(session):
+    """Update the scripts, to the latest versions."""
+    session.install("packaging", "requests", "cachecontrol[filecache]")
+
+    session.run("python", "scripts/generate.py")
+
+
+@nox.session(name="update-for-release")
+def update_for_release(session):
+    """Automation to run after a pip release."""
+    allowed_upstreams = [
+        "git@github.com:pypa/get-pip.git",
+        "https://github.com/pypa/get-pip.git",
+    ]
+
+    if len(session.posargs) != 1:
+        session.error("Usage: nox -s update-for-release -- <released-pip-version>")
+
+    release_version, = session.posargs
+
+    session.install("release-helper")
+    session.run("release-helper", "version-check-validity", release_version)
+    session.run("release-helper", "git-check-tag", release_version, "--does-not-exist")
+    session.run("release-helper", "git-check-remote", "upstream", *allowed_upstreams)
+    session.run("release-helper", "git-check-branch", "master")
+    session.run("release-helper", "git-check-clean")
+
+    # Generate the scripts.
+    generate(session)
+
+    # Make the commit and present it to the user.
+    session.run("git", "add", ".", external=True)
+    session.run(
+        "git", "commit", "-m", f"Update to {release_version}", external=True
+    )
+    session.run("git", "show", "HEAD", "--stat")
+
+    input(textwrap.dedent(
+        """\
+        **********************************************
+        * IMPORTANT: Check which files got modified. *
+        **********************************************
+
+        Press enter to continue. This script will generate a signed tag for this
+        commit and push it -- which will publish these changes.
+        """
+    ))
+
+    session.run(
+        # fmt: off
+        "git", "tag", release_version, "-m", f"Release {release_version}",
+        "--annotate", "--sign",
+        external=True,
+        # fmt: on
+    )
+    session.run("git", "push", "upstream", "master", release_version, external=True)
diff --git a/requirements.txt b/requirements.txt
deleted file mode 100644
index 0c13a44b..00000000
--- a/requirements.txt
+++ /dev/null
@@ -1,2 +0,0 @@
-invoke
-packaging
diff --git a/scripts/generate.py b/scripts/generate.py
new file mode 100644
index 00000000..e7e142e1
--- /dev/null
+++ b/scripts/generate.py
@@ -0,0 +1,197 @@
+"""Update all the get-pip.py scripts."""
+
+import hashlib
+import operator
+import re
+import subprocess
+import sys
+from base64 import b85encode
+from functools import lru_cache
+from io import BytesIO
+from pathlib import Path, PosixPath
+from typing import Dict, Iterable, List, Tuple
+from zipfile import ZipFile
+
+import requests
+from cachecontrol import CacheControl
+from cachecontrol.caches.file_cache import FileCache
+from packaging.specifiers import SpecifierSet
+from packaging.version import Version
+
+SCRIPT_CONSTRAINTS = {
+    "default": {
+        "pip": "",
+        "setuptools": "",
+        "wheel": "",
+    },
+    "2.6": {
+        "pip": "<10",
+        "setuptools": "<37",
+        "wheel": "<0.30",
+    },
+    "2.7": {
+        "pip": "<21.0",
+        "setuptools": "<45",
+        "wheel": "",
+    },
+    "3.2": {
+        "pip": "<8",
+        "setuptools": "<30",
+        "wheel": "<0.30",
+    },
+    "3.3": {
+        "pip": "<18",
+        "setuptools": "",
+        "wheel": "<0.30",
+    },
+    "3.4": {
+        "pip": "<19.2",
+        "setuptools": "",
+        "wheel": "",
+    },
+    "3.5": {
+        "pip": "<21.0",
+        "setuptools": "",
+        "wheel": "",
+    },
+}
+
+
+def get_all_pip_versions() -> Dict[Version, Tuple[str, str]]:
+    data = requests.get("https://pypi.python.org/pypi/pip/json").json()
+
+    versions = sorted(Version(s) for s in data["releases"].keys())
+
+    retval = {}
+    for version in versions:
+        wheels = [
+            (file["url"], file["md5_digest"])
+            for file in data["releases"][str(version)]
+            if file["url"].endswith(".whl")
+        ]
+        if not wheels:
+            continue
+        assert len(wheels) == 1, (version, wheels)
+        retval[version] = wheels[0]
+    return retval
+
+
+def determine_latest(versions: Iterable[Version], *, constraint: str):
+    assert sorted(versions) == list(versions)
+    return list(SpecifierSet(constraint).filter(versions))[-1]
+
+
+@lru_cache
+def get_ordered_templates() -> List[Tuple[Version, Path]]:
+    all_templates = list(Path("./templates").iterdir())
+
+    fallback = None
+    ordered_templates = []
+    for template in all_templates:
+        if template.name == "default.py":
+            fallback = template
+            continue
+        assert template.name.startswith("pre-")
+
+        version_str = template.name[4:-3]  # "pre-{version}.py"
+        version = Version(version_str)
+        ordered_templates.append((version, template))
+
+    # Use the epoch mechanism, to force the fallback to the end.
+    assert fallback is not None
+    ordered_templates.append((Version("1!0"), fallback))
+
+    # Order the (version, template) tuples, by increasing version numbers.
+    return sorted(ordered_templates, key=operator.itemgetter(0))
+
+
+def determine_template(version: Version):
+    ordered_templates = get_ordered_templates()
+    for template_version, template in ordered_templates:
+        if version < template_version:
+            return template
+    else:
+        assert template.name == "default.py"
+        return template
+
+
+def download_wheel(url: str, expected_md5: str) -> bytes:
+    session = requests.session()
+    cached_session = CacheControl(session, cache=FileCache(".web_cache"))
+
+    response = cached_session.get(url)
+    return response.content
+
+
+def repack_wheel(data: bytes):
+    """Remove the .dist-info, so that this is no longer a valid wheel."""
+    new_data = BytesIO()
+    with ZipFile(BytesIO(data)) as existing_zip:
+        with ZipFile(new_data, mode="w") as new_zip:
+            for zipinfo in existing_zip.infolist():
+                if re.search(r"pip-.+\.dist-info/", zipinfo.filename):
+                    continue
+                new_zip.writestr(zipinfo, existing_zip.read(zipinfo))
+
+    return new_data.getvalue()
+
+
+def encode_wheel_contents(data: bytes) -> str:
+    zipdata = b85encode(data).decode("utf8")
+
+    chunked = []
+    for i in range(0, len(zipdata), 79):
+        chunked.append(zipdata[i : i + 79])
+
+    return "\n".join(chunked)
+
+
+def determine_destination(version: str) -> Path:
+    public = Path(".")
+    if not public.exists():
+        public.mkdir()
+
+    if version == "default":
+        return public / "get-pip.py"
+
+    retval = public / version / "get-pip.py"
+    if not retval.parent.exists():
+        retval.parent.mkdir()
+
+    return retval
+
+
+def main() -> None:
+    print("Fetch available pip versions...")
+    pip_versions = get_all_pip_versions()
+
+    for version, mapping in SCRIPT_CONSTRAINTS.items():
+        print(f"Working on {version}")
+        destination = determine_destination(version)
+        pip_version = determine_latest(
+            pip_versions.keys(),
+            constraint=mapping["pip"],
+        )
+        template = determine_template(pip_version)
+
+        wheel_url, wheel_hash = pip_versions[pip_version]
+        print(f"  Downloading {PosixPath(wheel_url).name}")
+        original_wheel = download_wheel(wheel_url, wheel_hash)
+        repacked_wheel = repack_wheel(original_wheel)
+        encoded_wheel = encode_wheel_contents(repacked_wheel)
+
+        print(f"  Generating with {template}")
+        rendered_template = template.read_text().format(
+            zipfile=encoded_wheel,
+            installed_version=pip_version,
+            pip_version=mapping["pip"],
+            setuptools_version=mapping["setuptools"],
+            wheel_version=mapping["wheel"],
+        )
+
+        print(f"  Writing to {destination}")
+        destination.write_text(rendered_template)
+
+
+if __name__ == "__main__":
+    main()
diff --git a/tasks/__init__.py b/tasks/__init__.py
deleted file mode 100644
index 250fe9c4..00000000
--- a/tasks/__init__.py
+++ /dev/null
@@ -1,5 +0,0 @@
-import invoke
-
-from . import generate
-
-ns = invoke.Collection(generate)
diff --git a/tasks/generate.py b/tasks/generate.py
deleted file mode 100644
index 0933821c..00000000
--- a/tasks/generate.py
+++ /dev/null
@@ -1,150 +0,0 @@
-import base64
-import hashlib
-import io
-import json
-import os
-import os.path
-import re
-import zipfile
-
-import urllib.request
-
-import invoke
-import packaging.specifiers
-import packaging.version
-
-
-PROJECT_ROOT = os.path.abspath(os.path.dirname(os.path.dirname(__file__)))
-
-
-def _path(pyversion=None):
-    parts = [PROJECT_ROOT, pyversion, "get-pip.py"]
-    return os.path.join(*filter(None, parts))
-
-
-def _template(name="default.py"):
-    return os.path.join(PROJECT_ROOT, "templates", name)
-
-
-@invoke.task
-def installer(ctx,
-              pip_version=None, wheel_version=None, setuptools_version=None,
-              installer_path=_path(), template_path=_template()):
-
-    print("[generate.installer] Generating installer {} (using {})".format(
-        os.path.relpath(installer_path, PROJECT_ROOT),
-        "pip" + pip_version if pip_version is not None else "latest"
-    ))
-
-    # Load our wrapper template
-    with open(template_path, "r", encoding="utf8") as fp:
-        WRAPPER_TEMPLATE = fp.read()
-
-    # Get all of the versions on PyPI
-    resp = urllib.request.urlopen("https://pypi.python.org/pypi/pip/json")
-    data = json.loads(resp.read().decode("utf8"))
-    versions = sorted(data["releases"].keys(), key=packaging.version.parse)
-
-    # Filter our list of versions based on the given specifier
-    s = packaging.specifiers.SpecifierSet(
-        "" if pip_version is None else pip_version)
-    versions = list(s.filter(versions))
-
-    # Select the latest version that matches our specifier is
-    latest = versions[-1]
-
-    # Select the wheel file (we assume there will be only one per release)
-    file_urls = [
-        (x["url"], x["md5_digest"])
-        for x in data["releases"][latest]
-        if x["url"].endswith(".whl")
-    ]
-    assert len(file_urls) == 1
-    url, expected_hash = file_urls[0]
-
-    # Fetch the  file itself.
-    data = urllib.request.urlopen(url).read()
-    assert hashlib.md5(data).hexdigest() == expected_hash
-
-    # We need to repack the downloaded wheel file to remove the .dist-info,
-    # after this it will no longer be a valid wheel, but it will still work
-    # perfectly fine for our use cases.
-    new_data = io.BytesIO()
-    with zipfile.ZipFile(io.BytesIO(data)) as existing_zip:
-        with zipfile.ZipFile(new_data, mode="w") as new_zip:
-            for zinfo in existing_zip.infolist():
-                if re.search(r"pip-.+\.dist-info/", zinfo.filename):
-                    continue
-                new_zip.writestr(zinfo, existing_zip.read(zinfo))
-    data = new_data.getvalue()
-
-    # Write out the wrapper script that will take the place of the zip script
-    # The reason we need to do this instead of just directly executing the
-    # zip script is that while Python will happily execute a zip script if
-    # passed it on the file system, it will not however allow this to work if
-    # passed it via stdin. This means that this wrapper script is required to
-    # make ``curl https://...../get-pip.py | python`` continue to work.
-    print(
-        "[generate.installer] Write the wrapper script with the bundled zip "
-        "file"
-    )
-
-    zipdata = base64.b85encode(data).decode("utf8")
-    chunked = []
-
-    for i in range(0, len(zipdata), 79):
-        chunked.append(zipdata[i:i + 79])
-
-    os.makedirs(os.path.dirname(installer_path), exist_ok=True)
-    with open(installer_path, "w") as fp:
-        fp.write(
-            WRAPPER_TEMPLATE.format(
-                pip_version="" if pip_version is None else pip_version,
-                wheel_version="" if wheel_version is None else wheel_version,
-                setuptools_version=(
-                    "" if setuptools_version is None else setuptools_version),
-                installed_version=latest,
-                zipfile="\n".join(chunked),
-            ),
-        )
-
-    # Ensure the permissions on the newly created file
-    oldmode = os.stat(installer_path).st_mode & 0o7777
-    newmode = (oldmode | 0o555) & 0o7777
-    os.chmod(installer_path, newmode)
-
-    print("[generate.installer] Generated installer")
-
-
-@invoke.task(
-    default=True,
-    pre=[
-        invoke.call(installer),
-        invoke.call(installer, installer_path=_path("2.6"),
-                    template_path=_template("pre-10.py"),
-                    pip_version="<10",
-                    wheel_version="<0.30",
-                    setuptools_version="<37"),
-        invoke.call(installer, installer_path=_path("2.7"),
-                    template_path=_template("pre-21.0.py"),
-                    pip_version="<21.0",
-                    setuptools_version="<45"),
-        invoke.call(installer, installer_path=_path("3.2"),
-                    template_path=_template("pre-10.py"),
-                    pip_version="<8",
-                    wheel_version="<0.30",
-                    setuptools_version="<30"),
-        invoke.call(installer, installer_path=_path("3.3"),
-                    template_path=_template("pre-18.1.py"),
-                    pip_version="<18",
-                    wheel_version="<0.30"),
-        invoke.call(installer, installer_path=_path("3.4"),
-                    template_path=_template("pre-19.3.py"),
-                    pip_version="<19.2"),
-        invoke.call(installer, installer_path=_path("3.5"),
-                    template_path=_template("pre-21.0.py"),
-                    pip_version="<21.0"),
-    ],
-)
-def all(ctx):
-    pass
diff --git a/tests/__init__.py b/tests/__init__.py
deleted file mode 100644
index e69de29b..00000000
diff --git a/tests/test_basics.py b/tests/test_basics.py
deleted file mode 100644
index 7f2df179..00000000
--- a/tests/test_basics.py
+++ /dev/null
@@ -1,2 +0,0 @@
-def test_basics():
-    pass