diff --git a/public/2.6/get-pip.py b/public/2.6/get-pip.py
index b601fccb..b83a2ee6 100644
--- a/public/2.6/get-pip.py
+++ b/public/2.6/get-pip.py
@@ -147,11 +147,11 @@ def parse_args(self, args):
 
     # Add any implicit installations to the end of our args
     if implicit_pip:
-        args += ["pip<10"]
+        args += ["pip"]
     if implicit_setuptools:
-        args += ["setuptools<37"]
+        args += ["setuptools"]
     if implicit_wheel:
-        args += ["wheel<0.30"]
+        args += ["wheel"]
 
     delete_tmpdir = False
     try:
diff --git a/public/2.7/get-pip.py b/public/2.7/get-pip.py
index 3ef3d705..c2064943 100644
--- a/public/2.7/get-pip.py
+++ b/public/2.7/get-pip.py
@@ -149,9 +149,9 @@ def cert_parse_args(self, args):
 
     # Add any implicit installations to the end of our args
     if implicit_pip:
-        args += ["pip<21.0"]
+        args += ["pip"]
     if implicit_setuptools:
-        args += ["setuptools<45"]
+        args += ["setuptools"]
     if implicit_wheel:
         args += ["wheel"]
 
diff --git a/public/3.3/get-pip.py b/public/3.3/get-pip.py
index 77be6b0f..c5fb4a97 100644
--- a/public/3.3/get-pip.py
+++ b/public/3.3/get-pip.py
@@ -147,11 +147,11 @@ def parse_args(self, args):
 
     # Add any implicit installations to the end of our args
     if implicit_pip:
-        args += ["pip<18"]
+        args += ["pip"]
     if implicit_setuptools:
         args += ["setuptools"]
     if implicit_wheel:
-        args += ["wheel<0.30"]
+        args += ["wheel"]
 
     # Add our default arguments
     args = ["install", "--upgrade", "--force-reinstall"] + args
diff --git a/public/3.4/get-pip.py b/public/3.4/get-pip.py
index a52adebc..759d72e6 100644
--- a/public/3.4/get-pip.py
+++ b/public/3.4/get-pip.py
@@ -147,7 +147,7 @@ def parse_args(self, args):
 
     # Add any implicit installations to the end of our args
     if implicit_pip:
-        args += ["pip<19.2"]
+        args += ["pip"]
     if implicit_setuptools:
         args += ["setuptools"]
     if implicit_wheel:
diff --git a/public/3.5/get-pip.py b/public/3.5/get-pip.py
index 0761be8a..c2064943 100644
--- a/public/3.5/get-pip.py
+++ b/public/3.5/get-pip.py
@@ -149,7 +149,7 @@ def cert_parse_args(self, args):
 
     # Add any implicit installations to the end of our args
     if implicit_pip:
-        args += ["pip<21.0"]
+        args += ["pip"]
     if implicit_setuptools:
         args += ["setuptools"]
     if implicit_wheel:
diff --git a/public/3.6/get-pip.py b/public/3.6/get-pip.py
index efc3a26c..6ee0c6af 100644
--- a/public/3.6/get-pip.py
+++ b/public/3.6/get-pip.py
@@ -71,7 +71,7 @@ def determine_pip_install_arguments():
     pre_parser.add_argument("--no-wheel", action="store_true")
     pre, args = pre_parser.parse_known_args()
 
-    args.append("pip<22.0")
+    args.append("pip")
 
     if include_setuptools(pre):
         args.append("setuptools")
diff --git a/public/3.7/get-pip.py b/public/3.7/get-pip.py
index ca5622ec..0d1fc4e1 100644
--- a/public/3.7/get-pip.py
+++ b/public/3.7/get-pip.py
@@ -71,7 +71,7 @@ def determine_pip_install_arguments():
     pre_parser.add_argument("--no-wheel", action="store_true")
     pre, args = pre_parser.parse_known_args()
 
-    args.append("pip<24.1")
+    args.append("pip")
 
     if include_setuptools(pre):
         args.append("setuptools")
diff --git a/scripts/generate.py b/scripts/generate.py
index d6fd75b7..36993540 100644
--- a/scripts/generate.py
+++ b/scripts/generate.py
@@ -23,48 +23,34 @@
 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 older than v9.0.0 does not support Requires-Python so we have to manually
+        # constrain the pip, setuptools and wheel versions that are installed at runtime.
         "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": "",
     },
     "3.6": {
         "pip": "<22.0",
-        "setuptools": "",
-        "wheel": "",
     },
     "3.7": {
         "pip": "<24.1",
-        "setuptools": "",
-        "wheel": "",
     },
 }
 
@@ -248,7 +234,7 @@ def detect_newline(f: TextIO) -> str:
 
 
 def generate_one(variant, mapping, *, console, pip_versions):
-    # Determing the correct wheel to download
+    # Determine the correct wheel to download
     pip_version = determine_latest(pip_versions.keys(), constraint=mapping["pip"])
     wheel_url, wheel_hash = pip_versions[pip_version]
 
@@ -264,10 +250,11 @@ def generate_one(variant, mapping, *, console, pip_versions):
         newline = detect_newline(f)
         rendered_template = f.read().format(
             zipfile=encoded_wheel,
-            installed_version=pip_version,
-            pip_version=mapping["pip"],
-            setuptools_version=mapping["setuptools"],
-            wheel_version=mapping["wheel"],
+            bundled_pip_version=pip_version,
+            # These constraints are only used for pip versions that don't support Requires-Python.
+            pip_version_constraint=mapping.get("pip"),
+            setuptools_version_constraint=mapping.get("setuptools"),
+            wheel_version_constraint=mapping.get("wheel"),
             minimum_supported_version=mapping["minimum_supported_version"],
         )
     # Write the script to the correct location
diff --git a/templates/default.py b/templates/default.py
index 01f27a33..c90cc3d5 100644
--- a/templates/default.py
+++ b/templates/default.py
@@ -5,7 +5,7 @@
 # You may be wondering what this giant blob of binary data here is, you might
 # even be worried that we're up to something nefarious (good for you for being
 # paranoid!). This is a base85 encoding of a zip file, this zip file contains
-# an entire copy of pip (version {installed_version}).
+# an entire copy of pip (version {bundled_pip_version}).
 #
 # Pip is a thing that installs packages, pip itself is a package that someone
 # might want to install, especially if they're looking to run this get-pip.py
@@ -71,13 +71,13 @@ def determine_pip_install_arguments():
     pre_parser.add_argument("--no-wheel", action="store_true")
     pre, args = pre_parser.parse_known_args()
 
-    args.append("pip{pip_version}")
+    args.append("pip")
 
     if include_setuptools(pre):
-        args.append("setuptools{setuptools_version}")
+        args.append("setuptools")
 
     if include_wheel(pre):
-        args.append("wheel{wheel_version}")
+        args.append("wheel")
 
     return ["install", "--upgrade", "--force-reinstall"] + args
 
diff --git a/templates/pre-10.py b/templates/pre-10.py
index acbea9d8..280a1d8c 100644
--- a/templates/pre-10.py
+++ b/templates/pre-10.py
@@ -5,7 +5,7 @@
 # You may be wondering what this giant blob of binary data here is, you might
 # even be worried that we're up to something nefarious (good for you for being
 # paranoid!). This is a base85 encoding of a zip file, this zip file contains
-# an entire copy of pip (version {installed_version}).
+# an entire copy of pip (version {bundled_pip_version}).
 #
 # Pip is a thing that installs packages, pip itself is a package that someone
 # might want to install, especially if they're looking to run this get-pip.py
@@ -147,11 +147,11 @@ def parse_args(self, args):
 
     # Add any implicit installations to the end of our args
     if implicit_pip:
-        args += ["pip{pip_version}"]
+        args += ["pip"]
     if implicit_setuptools:
-        args += ["setuptools{setuptools_version}"]
+        args += ["setuptools"]
     if implicit_wheel:
-        args += ["wheel{wheel_version}"]
+        args += ["wheel"]
 
     delete_tmpdir = False
     try:
diff --git a/templates/pre-18.1.py b/templates/pre-18.1.py
index dd10d083..dfe760f8 100644
--- a/templates/pre-18.1.py
+++ b/templates/pre-18.1.py
@@ -5,7 +5,7 @@
 # You may be wondering what this giant blob of binary data here is, you might
 # even be worried that we're up to something nefarious (good for you for being
 # paranoid!). This is a base85 encoding of a zip file, this zip file contains
-# an entire copy of pip (version {installed_version}).
+# an entire copy of pip (version {bundled_pip_version}).
 #
 # Pip is a thing that installs packages, pip itself is a package that someone
 # might want to install, especially if they're looking to run this get-pip.py
@@ -147,11 +147,11 @@ def parse_args(self, args):
 
     # Add any implicit installations to the end of our args
     if implicit_pip:
-        args += ["pip{pip_version}"]
+        args += ["pip"]
     if implicit_setuptools:
-        args += ["setuptools{setuptools_version}"]
+        args += ["setuptools"]
     if implicit_wheel:
-        args += ["wheel{wheel_version}"]
+        args += ["wheel"]
 
     # Add our default arguments
     args = ["install", "--upgrade", "--force-reinstall"] + args
diff --git a/templates/pre-19.3.py b/templates/pre-19.3.py
index 38fb75c4..1d198f4c 100644
--- a/templates/pre-19.3.py
+++ b/templates/pre-19.3.py
@@ -5,7 +5,7 @@
 # You may be wondering what this giant blob of binary data here is, you might
 # even be worried that we're up to something nefarious (good for you for being
 # paranoid!). This is a base85 encoding of a zip file, this zip file contains
-# an entire copy of pip (version {installed_version}).
+# an entire copy of pip (version {bundled_pip_version}).
 #
 # Pip is a thing that installs packages, pip itself is a package that someone
 # might want to install, especially if they're looking to run this get-pip.py
@@ -147,11 +147,11 @@ def parse_args(self, args):
 
     # Add any implicit installations to the end of our args
     if implicit_pip:
-        args += ["pip{pip_version}"]
+        args += ["pip"]
     if implicit_setuptools:
-        args += ["setuptools{setuptools_version}"]
+        args += ["setuptools"]
     if implicit_wheel:
-        args += ["wheel{wheel_version}"]
+        args += ["wheel"]
 
     # Add our default arguments
     args = ["install", "--upgrade", "--force-reinstall"] + args
diff --git a/templates/pre-21.0.py b/templates/pre-21.0.py
index 038c6249..6006bfdf 100644
--- a/templates/pre-21.0.py
+++ b/templates/pre-21.0.py
@@ -5,7 +5,7 @@
 # You may be wondering what this giant blob of binary data here is, you might
 # even be worried that we're up to something nefarious (good for you for being
 # paranoid!). This is a base85 encoding of a zip file, this zip file contains
-# an entire copy of pip (version {installed_version}).
+# an entire copy of pip (version {bundled_pip_version}).
 #
 # Pip is a thing that installs packages, pip itself is a package that someone
 # might want to install, especially if they're looking to run this get-pip.py
@@ -149,11 +149,11 @@ def cert_parse_args(self, args):
 
     # Add any implicit installations to the end of our args
     if implicit_pip:
-        args += ["pip{pip_version}"]
+        args += ["pip"]
     if implicit_setuptools:
-        args += ["setuptools{setuptools_version}"]
+        args += ["setuptools"]
     if implicit_wheel:
-        args += ["wheel{wheel_version}"]
+        args += ["wheel"]
 
     # Add our default arguments
     args = ["install", "--upgrade", "--force-reinstall"] + args
diff --git a/templates/pre-9.py b/templates/pre-9.py
new file mode 100644
index 00000000..232f48c6
--- /dev/null
+++ b/templates/pre-9.py
@@ -0,0 +1,207 @@
+#!/usr/bin/env python
+#
+# Hi There!
+#
+# You may be wondering what this giant blob of binary data here is, you might
+# even be worried that we're up to something nefarious (good for you for being
+# paranoid!). This is a base85 encoding of a zip file, this zip file contains
+# an entire copy of pip (version {bundled_pip_version}).
+#
+# Pip is a thing that installs packages, pip itself is a package that someone
+# might want to install, especially if they're looking to run this get-pip.py
+# script. Pip has a lot of code to deal with the security of installing
+# packages, various edge cases on various platforms, and other such sort of
+# "tribal knowledge" that has been encoded in its code base. Because of this
+# we basically include an entire copy of pip inside this blob. We do this
+# because the alternatives are attempt to implement a "minipip" that probably
+# doesn't do things correctly and has weird edge cases, or compress pip itself
+# down into a single file.
+#
+# If you're wondering how this is created, it is generated using
+# `scripts/generate.py` in https://github.com/pypa/get-pip.
+
+import os.path
+import pkgutil
+import shutil
+import sys
+import struct
+import tempfile
+
+# Useful for very coarse version differentiation.
+PY2 = sys.version_info[0] == 2
+PY3 = sys.version_info[0] == 3
+
+if PY3:
+    iterbytes = iter
+else:
+    def iterbytes(buf):
+        return (ord(byte) for byte in buf)
+
+try:
+    from base64 import b85decode
+except ImportError:
+    _b85alphabet = (b"0123456789ABCDEFGHIJKLMNOPQRSTUVWXYZ"
+                    b"abcdefghijklmnopqrstuvwxyz!#$%&()*+-;<=>?@^_`{{|}}~")
+
+    def b85decode(b):
+        _b85dec = [None] * 256
+        for i, c in enumerate(iterbytes(_b85alphabet)):
+            _b85dec[c] = i
+
+        padding = (-len(b)) % 5
+        b = b + b'~' * padding
+        out = []
+        packI = struct.Struct('!I').pack
+        for i in range(0, len(b), 5):
+            chunk = b[i:i + 5]
+            acc = 0
+            try:
+                for c in iterbytes(chunk):
+                    acc = acc * 85 + _b85dec[c]
+            except TypeError:
+                for j, c in enumerate(iterbytes(chunk)):
+                    if _b85dec[c] is None:
+                        raise ValueError(
+                            'bad base85 character at position %d' % (i + j)
+                        )
+                raise
+            try:
+                out.append(packI(acc))
+            except struct.error:
+                raise ValueError('base85 overflow in hunk starting at byte %d'
+                                 % i)
+
+        result = b''.join(out)
+        if padding:
+            result = result[:-padding]
+        return result
+
+
+def bootstrap(tmpdir=None):
+    # Import pip so we can use it to install pip and maybe setuptools too
+    import pip
+    from pip.commands.install import InstallCommand
+    from pip.req import InstallRequirement
+
+    # Wrapper to provide default certificate with the lowest priority
+    class CertInstallCommand(InstallCommand):
+        def parse_args(self, args):
+            # If cert isn't specified in config or environment, we provide our
+            # own certificate through defaults.
+            # This allows user to specify custom cert anywhere one likes:
+            # config, environment variable or argv.
+            if not self.parser.get_default_values().cert:
+                self.parser.defaults["cert"] = cert_path  # calculated below
+            return super(CertInstallCommand, self).parse_args(args)
+
+    pip.commands_dict["install"] = CertInstallCommand
+
+    implicit_pip = True
+    implicit_setuptools = True
+    implicit_wheel = True
+
+    # Check if the user has requested us not to install setuptools
+    if "--no-setuptools" in sys.argv or os.environ.get("PIP_NO_SETUPTOOLS"):
+        args = [x for x in sys.argv[1:] if x != "--no-setuptools"]
+        implicit_setuptools = False
+    else:
+        args = sys.argv[1:]
+
+    # Check if the user has requested us not to install wheel
+    if "--no-wheel" in args or os.environ.get("PIP_NO_WHEEL"):
+        args = [x for x in args if x != "--no-wheel"]
+        implicit_wheel = False
+
+    # We only want to implicitly install setuptools and wheel if they don't
+    # already exist on the target platform.
+    if implicit_setuptools:
+        try:
+            import setuptools  # noqa
+            implicit_setuptools = False
+        except ImportError:
+            pass
+    if implicit_wheel:
+        try:
+            import wheel  # noqa
+            implicit_wheel = False
+        except ImportError:
+            pass
+
+    # We want to support people passing things like 'pip<8' to get-pip.py which
+    # will let them install a specific version. However because of the dreaded
+    # DoubleRequirement error if any of the args look like they might be a
+    # specific for one of our packages, then we'll turn off the implicit
+    # install of them.
+    for arg in args:
+        try:
+            req = InstallRequirement.from_line(arg)
+        except Exception:
+            continue
+
+        if implicit_pip and req.name == "pip":
+            implicit_pip = False
+        elif implicit_setuptools and req.name == "setuptools":
+            implicit_setuptools = False
+        elif implicit_wheel and req.name == "wheel":
+            implicit_wheel = False
+
+    # Add any implicit installations to the end of our args
+    if implicit_pip:
+        args += ["pip{pip_version_constraint}"]
+    if implicit_setuptools:
+        args += ["setuptools{setuptools_version_constraint}"]
+    if implicit_wheel:
+        args += ["wheel{wheel_version_constraint}"]
+
+    delete_tmpdir = False
+    try:
+        # Create a temporary directory to act as a working directory if we were
+        # not given one.
+        if tmpdir is None:
+            tmpdir = tempfile.mkdtemp()
+            delete_tmpdir = True
+
+        # We need to extract the SSL certificates from requests so that they
+        # can be passed to --cert
+        cert_path = os.path.join(tmpdir, "cacert.pem")
+        with open(cert_path, "wb") as cert:
+            cert.write(pkgutil.get_data("pip._vendor.requests", "cacert.pem"))
+
+        # Execute the included pip and use it to install the latest pip and
+        # setuptools from PyPI
+        sys.exit(pip.main(["install", "--upgrade"] + args))
+    finally:
+        # Remove our temporary directory
+        if delete_tmpdir and tmpdir:
+            shutil.rmtree(tmpdir, ignore_errors=True)
+
+
+def main():
+    tmpdir = None
+    try:
+        # Create a temporary working directory
+        tmpdir = tempfile.mkdtemp()
+
+        # Unpack the zipfile into the temporary directory
+        pip_zip = os.path.join(tmpdir, "pip.zip")
+        with open(pip_zip, "wb") as fp:
+            fp.write(b85decode(DATA.replace(b"\n", b"")))
+
+        # Add the zipfile to sys.path so that we can import it
+        sys.path.insert(0, pip_zip)
+
+        # Run the bootstrap
+        bootstrap(tmpdir=tmpdir)
+    finally:
+        # Clean up our temporary working directory
+        if tmpdir:
+            shutil.rmtree(tmpdir, ignore_errors=True)
+
+
+DATA = b"""
+{zipfile}
+"""
+
+
+if __name__ == "__main__":
+    main()