diff --git a/CHANGES.md b/CHANGES.md
index c77aa1120..90290589d 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -1,5 +1,15 @@
 # Release Notes
 
+## 2.17.0
+
+This release brings support for overriding the versions of setuptools
+and wheel Pex bootstraps for non-vendored Pip versions (the modern ones
+you select with `--pip-version`) using the existing
+`--extra-pip-requirement` option introduced in the [2.10.0 release](
+https://github.com/pex-tool/pex/releases/tag/v2.10.0).
+
+* Support custom setuptools & wheel versions. (#2514)
+
 ## 2.16.2
 
 This release brings a slew of small fixes across the code base.
diff --git a/pex/build_system/pep_517.py b/pex/build_system/pep_517.py
index f7d87ef93..22de3925d 100644
--- a/pex/build_system/pep_517.py
+++ b/pex/build_system/pep_517.py
@@ -45,7 +45,7 @@ def _default_build_system(
             resolved_reqs = set()  # type: Set[str]
             resolved_dists = []  # type: List[Distribution]
             if selected_pip_version is PipVersion.VENDORED:
-                requires = ["setuptools", selected_pip_version.wheel_requirement]
+                requires = ["setuptools", str(selected_pip_version.wheel_requirement)]
                 resolved_dists.extend(
                     Distribution.load(dist_location)
                     for dist_location in third_party.expose(
@@ -56,8 +56,8 @@ def _default_build_system(
                 extra_env.update(__PEX_UNVENDORED__="setuptools")
             else:
                 requires = [
-                    selected_pip_version.setuptools_requirement,
-                    selected_pip_version.wheel_requirement,
+                    str(selected_pip_version.setuptools_requirement),
+                    str(selected_pip_version.wheel_requirement),
                 ]
             unresolved = [
                 requirement for requirement in requires if requirement not in resolved_reqs
diff --git a/pex/pip/installation.py b/pex/pip/installation.py
index 0ef28406e..176f1e1ca 100644
--- a/pex/pip/installation.py
+++ b/pex/pip/installation.py
@@ -5,6 +5,7 @@
 
 import hashlib
 import os
+from collections import OrderedDict
 from textwrap import dedent
 
 from pex import pex_warnings, third_party
@@ -13,6 +14,7 @@
 from pex.dist_metadata import Requirement
 from pex.interpreter import PythonInterpreter
 from pex.orderedset import OrderedSet
+from pex.pep_503 import ProjectName
 from pex.pex import PEX
 from pex.pex_bootstrapper import ensure_venv
 from pex.pip.tool import Pip, PipVenv
@@ -21,6 +23,7 @@
 from pex.result import Error, try_
 from pex.targets import LocalInterpreter, RequiresPythonError, Targets
 from pex.third_party import isolated
+from pex.tracer import TRACER
 from pex.typing import TYPE_CHECKING
 from pex.util import named_temporary_file
 from pex.variables import ENV
@@ -86,6 +89,11 @@ def _fingerprint(requirements):
     return hashlib.sha1("\n".join(sorted(map(str, requirements))).encode("utf-8")).hexdigest()
 
 
+_PIP_PROJECT_NAME = ProjectName("pip")
+_SETUPTOOLS_PROJECT_NAME = ProjectName("setuptools")
+_WHEEL_PROJECT_NAME = ProjectName("wheel")
+
+
 def _vendored_installation(
     interpreter=None,  # type: Optional[PythonInterpreter]
     resolver=None,  # type: Optional[Resolver]
@@ -114,6 +122,33 @@ def expose_vendored():
             )
         )
 
+    # Ensure user-specified extra requirements do not override vendored Pip or its setuptools and
+    # wheel dependencies. These are arranged just so with some patching to Pip and setuptools as
+    # well as a low enough standard wheel version to support Python 2.7.
+    for extra_req in extra_requirements:
+        if _PIP_PROJECT_NAME == extra_req.project_name:
+            raise ValueError(
+                "An `--extra-pip-requirement` cannot be used to override the Pip version; use "
+                "`--pip-version` to select a supported Pip version instead. "
+                "Given: {pip_req}".format(pip_req=extra_req)
+            )
+        if _SETUPTOOLS_PROJECT_NAME == extra_req.project_name:
+            raise ValueError(
+                "An `--extra-pip-requirement` cannot be used to override the setuptools version "
+                "for vendored Pip. If you need a custom setuptools you need to use `--pip-version` "
+                "to select a non-vendored Pip version. Given: {setuptools_req}".format(
+                    setuptools_req=extra_req
+                )
+            )
+        if _WHEEL_PROJECT_NAME == extra_req.project_name:
+            raise ValueError(
+                "An `--extra-pip-requirement` cannot be used to override the wheel version for "
+                "vendored Pip. If you need a custom wheel version you need to use `--pip-version` "
+                "to select a non-vendored Pip version. Given: {wheel_req}".format(
+                    wheel_req=extra_req
+                )
+            )
+
     # This indirection works around MyPy type inference failing to see that
     # `iter_distribution_locations` is only successfully defined when resolve is not None.
     extra_requirement_resolver = resolver
@@ -156,9 +191,9 @@ def bootstrap_pip():
         )
 
         for req in version.requirements:
-            project_name = Requirement.parse(req).name
+            project_name = req.name
             target_dir = os.path.join(chroot, "reqs", project_name)
-            venv.interpreter.execute(["-m", "pip", "install", "--target", target_dir, req])
+            venv.interpreter.execute(["-m", "pip", "install", "--target", target_dir, str(req)])
             yield target_dir
 
     return bootstrap_pip
@@ -189,20 +224,40 @@ def _resolved_installation(
             fingerprint=_fingerprint(extra_requirements),
         )
 
-    requirements = list(version.requirements)
-    requirements.extend(map(str, extra_requirements))
+    requirements_by_project_name = OrderedDict(
+        (req.project_name, str(req)) for req in version.requirements
+    )
+
+    # Allow user-specified extra requirements to override Pip requirements (setuptools and wheel).
+    for extra_req in extra_requirements:
+        if _PIP_PROJECT_NAME == extra_req.project_name:
+            raise ValueError(
+                "An `--extra-pip-requirement` cannot be used to override the Pip version; use "
+                "`--pip-version` to select a supported Pip version instead. "
+                "Given: {pip_req}".format(pip_req=extra_req)
+            )
+        existing_req = requirements_by_project_name.get(extra_req.project_name)
+        if existing_req:
+            TRACER.log(
+                "Overriding `--pip-version {pip_version}` requirement of {existing_req} with "
+                "user-specified requirement {extra_req}".format(
+                    pip_version=version.version, existing_req=existing_req, extra_req=extra_req
+                )
+            )
+        requirements_by_project_name[extra_req.project_name] = str(extra_req)
+
     if not resolver:
         raise ValueError(
             "A resolver is required to install {requirements} for Pip {version}: {reqs}".format(
-                requirements=pluralize(requirements, "requirement"),
+                requirements=pluralize(requirements_by_project_name, "requirement"),
                 version=version,
-                reqs=" ".join(map(str, extra_requirements)),
+                reqs=" ".join(requirements_by_project_name.values()),
             )
         )
 
     def resolve_distribution_locations():
         for resolved_distribution in resolver.resolve_requirements(
-            requirements=requirements,
+            requirements=requirements_by_project_name.values(),
             targets=targets,
             pip_version=bootstrap_pip_version,
             extra_resolver_requirements=(),
diff --git a/pex/pip/tool.py b/pex/pip/tool.py
index dd6228e68..5ead11bd6 100644
--- a/pex/pip/tool.py
+++ b/pex/pip/tool.py
@@ -293,6 +293,11 @@ class Pip(object):
     version = attr.ib()  # type: PipVersionValue
     _pip_cache = attr.ib()  # type: str
 
+    @property
+    def venv_dir(self):
+        # type: () -> str
+        return self._pip.venv_dir
+
     @staticmethod
     def _calculate_resolver_version(package_index_configuration=None):
         # type: (Optional[PackageIndexConfiguration]) -> ResolverVersion.Value
@@ -643,7 +648,7 @@ def _ensure_wheel_installed(self, package_index_configuration=None):
             if not atomic_dir.is_finalized():
                 self.spawn_download_distributions(
                     download_dir=atomic_dir.work_dir,
-                    requirements=[self.version.wheel_requirement],
+                    requirements=[str(self.version.wheel_requirement)],
                     package_index_configuration=package_index_configuration,
                     build_configuration=BuildConfiguration.create(allow_builds=False),
                 ).wait()
diff --git a/pex/pip/version.py b/pex/pip/version.py
index aeaa96465..2fce6b02c 100644
--- a/pex/pip/version.py
+++ b/pex/pip/version.py
@@ -58,8 +58,8 @@ def to_requirement(
             project_name,  # type: str
             project_version=None,  # type: Optional[str]
         ):
-            # type: (...) -> str
-            return (
+            # type: (...) -> Requirement
+            return Requirement.parse(
                 "{project_name}=={project_version}".format(
                     project_name=project_name, project_version=project_version
                 )
@@ -68,7 +68,9 @@ def to_requirement(
             )
 
         self.version = Version(version)
-        self.requirement = requirement or to_requirement("pip", version)
+        self.requirement = (
+            Requirement.parse(requirement) if requirement else to_requirement("pip", version)
+        )
         self.setuptools_requirement = to_requirement("setuptools", setuptools_version)
         self.wheel_requirement = to_requirement("wheel", wheel_version)
         self.requires_python = SpecifierSet(requires_python) if requires_python else None
@@ -76,11 +78,11 @@ def to_requirement(
 
     @property
     def requirements(self):
-        # type: () -> Iterable[str]
+        # type: () -> Iterable[Requirement]
         return self.requirement, self.setuptools_requirement, self.wheel_requirement
 
     def requires_python_applies(self, target=None):
-        # type: (Optional[Union[Version,Target]]) -> bool
+        # type: (Optional[Union[Version, Target]]) -> bool
         if not self.requires_python:
             return True
 
@@ -89,10 +91,7 @@ def requires_python_applies(self, target=None):
 
         return LocalInterpreter.create(
             interpreter=target.get_interpreter() if target else None
-        ).requires_python_applies(
-            requires_python=self.requires_python,
-            source=Requirement.parse(self.requirement),
-        )
+        ).requires_python_applies(requires_python=self.requires_python, source=self.requirement)
 
     def __lt__(self, other):
         if not isinstance(other, PipVersionValue):
@@ -180,10 +179,6 @@ def values(cls):
         requires_python="<3.12",
     )
 
-    # TODO(John Sirois): Expose setuptools and wheel version flags - these don't affect
-    #  Pex; so we should allow folks to experiment with upgrade easily:
-    #  https://github.com/pex-tool/pex/issues/1895
-
     v22_2_2 = PipVersionValue(
         version="22.2.2",
         setuptools_version="65.3.0",
diff --git a/pex/version.py b/pex/version.py
index cd272f8c2..3703e2501 100644
--- a/pex/version.py
+++ b/pex/version.py
@@ -1,4 +1,4 @@
 # Copyright 2015 Pex project contributors.
 # Licensed under the Apache License, Version 2.0 (see LICENSE).
 
-__version__ = "2.16.2"
+__version__ = "2.17.0"
diff --git a/tests/integration/cli/commands/test_lock_sync.py b/tests/integration/cli/commands/test_lock_sync.py
index 673b87a80..6c6eb4d65 100644
--- a/tests/integration/cli/commands/test_lock_sync.py
+++ b/tests/integration/cli/commands/test_lock_sync.py
@@ -89,8 +89,8 @@ def host_requirements(*requirements):
             # itself if needed.
             host_requirements(
                 "cowsay==5.0.0",
-                pip_version.setuptools_requirement,
-                pip_version.wheel_requirement,
+                str(pip_version.setuptools_requirement),
+                str(pip_version.wheel_requirement),
             )
             find_links_repo.make_sdist("spam", version="1")
             find_links_repo.make_wheel("spam", version="1")
diff --git a/tests/integration/cli/commands/test_lock_update.py b/tests/integration/cli/commands/test_lock_update.py
index 505e6e610..1f98b6063 100644
--- a/tests/integration/cli/commands/test_lock_update.py
+++ b/tests/integration/cli/commands/test_lock_update.py
@@ -80,8 +80,8 @@ def find_links(
     repository_pex = os.path.join(str(tmpdir), "repository.pex")
     run_pex_command(
         args=[
-            pip_version.setuptools_requirement,
-            pip_version.wheel_requirement,
+            str(pip_version.setuptools_requirement),
+            str(pip_version.wheel_requirement),
             "--include-tools",
             "-o",
             repository_pex,
diff --git a/tests/integration/test_issue_2343.py b/tests/integration/test_issue_2343.py
index 463348cff..4ed4ae656 100644
--- a/tests/integration/test_issue_2343.py
+++ b/tests/integration/test_issue_2343.py
@@ -41,8 +41,8 @@ def find_links(shared_integration_test_tmpdir):
             result = find_links_repo.resolver.resolve_requirements(
                 [
                     "ansicolors==1.1.8",
-                    pip_version.setuptools_requirement,
-                    pip_version.wheel_requirement,
+                    str(pip_version.setuptools_requirement),
+                    str(pip_version.wheel_requirement),
                 ],
                 result_type=InstallableType.WHEEL_FILE,
             )
diff --git a/tests/integration/test_keyring_support.py b/tests/integration/test_keyring_support.py
index ec3bd0c4e..3c5a50c80 100644
--- a/tests/integration/test_keyring_support.py
+++ b/tests/integration/test_keyring_support.py
@@ -201,7 +201,7 @@ def download_pip_requirements(
     extra_requirements=(),  # type: Iterable[str]
 ):
     # type: (...) -> None
-    requirements = list(pip_version.requirements)
+    requirements = list(map(str, pip_version.requirements))
     requirements.extend(extra_requirements)
     get_pip(resolver=ConfiguredResolver.version(pip_version)).spawn_download_distributions(
         download_dir=download_dir, requirements=requirements
diff --git a/tests/test_bdist_pex.py b/tests/test_bdist_pex.py
index fdc91d4d9..650fada08 100644
--- a/tests/test_bdist_pex.py
+++ b/tests/test_bdist_pex.py
@@ -219,7 +219,7 @@ def test_unwriteable_contents():
         wheels.extend(
             fingerprinted_dist.distribution.location
             for fingerprinted_dist in resolve(
-                requirements=[PipVersion.VENDORED.wheel_requirement],
+                requirements=[str(PipVersion.VENDORED.wheel_requirement)],
                 result_type=InstallableType.WHEEL_FILE,
             ).distributions
         )
diff --git a/tests/test_pip.py b/tests/test_pip.py
index 0bc0bbe15..18454b838 100644
--- a/tests/test_pip.py
+++ b/tests/test_pip.py
@@ -6,14 +6,19 @@
 import hashlib
 import json
 import os
+import re
 import shutil
 import warnings
+from typing import Dict
 
 import pytest
 
 from pex.common import safe_rmtree
+from pex.dist_metadata import Distribution, Requirement
 from pex.interpreter import PythonInterpreter
 from pex.jobs import Job
+from pex.pep_440 import Version
+from pex.pep_503 import ProjectName
 from pex.pip.installation import _PIP, PipInstallation, get_pip
 from pex.pip.tool import PackageIndexConfiguration, Pip
 from pex.pip.version import PipVersion, PipVersionValue
@@ -23,16 +28,18 @@
 from pex.targets import AbbreviatedPlatform, LocalInterpreter, Target
 from pex.typing import TYPE_CHECKING
 from pex.variables import ENV
+from pex.venv.virtualenv import Virtualenv
 from testing import IS_LINUX, PY310, ensure_python_interpreter, environment_as
 
 if TYPE_CHECKING:
-    from typing import Any, Iterator, Optional, Protocol
+    from typing import Any, Iterable, Iterator, Optional, Protocol
 
     class CreatePip(Protocol):
         def __call__(
             self,
             interpreter,  # type: Optional[PythonInterpreter]
             version=PipVersion.DEFAULT,  # type: PipVersionValue
+            extra_requirements=(),  # type: Iterable[Requirement]
             **extra_env  # type: str
         ):
             # type: (...) -> Pip
@@ -62,12 +69,16 @@ def create_pip(
     def create_pip(
         interpreter,  # type: Optional[PythonInterpreter]
         version=PipVersion.DEFAULT,  # type: PipVersionValue
+        extra_requirements=(),  # type: Iterable[Requirement]
         **extra_env  # type: str
     ):
         # type: (...) -> Pip
         with ENV.patch(PEX_ROOT=pex_root, **extra_env):
             return get_pip(
-                interpreter=interpreter, version=version, resolver=ConfiguredResolver.default()
+                interpreter=interpreter,
+                version=version,
+                resolver=ConfiguredResolver.default(),
+                extra_requirements=tuple(extra_requirements),
             )
 
     yield create_pip
@@ -382,3 +393,135 @@ def test_use_pip_config(
             job.wait()
         assert not os.path.exists(download_dir)
         assert "invalid --python-version value: 'invalid'" in str(exc.value.stderr)
+
+
+@applicable_pip_versions
+def test_extra_pip_requirements_pip_not_allowed(
+    create_pip,  # type: CreatePip
+    version,  # type: PipVersionValue
+    current_interpreter,  # type: PythonInterpreter
+):
+    # type: (...) -> None
+
+    with pytest.raises(
+        ValueError,
+        match=re.escape(
+            "An `--extra-pip-requirement` cannot be used to override the Pip version; use "
+            "`--pip-version` to select a supported Pip version instead. Given: pip~=24.0"
+        ),
+    ):
+        create_pip(
+            current_interpreter,
+            version=version,
+            extra_requirements=[Requirement.parse("pip~=24.0")],
+        )
+
+
+def index_pip_distributions(
+    create_pip,  # type: CreatePip
+    current_interpreter,  # type: PythonInterpreter
+    version,  # type: PipVersionValue
+    extra_requirement,  # type: str
+):
+    # type: (...) -> Dict[ProjectName, Distribution]
+
+    pip = create_pip(
+        current_interpreter,
+        version=version,
+        extra_requirements=[Requirement.parse(extra_requirement)],
+    )
+    dists_by_project_name = {
+        dist.metadata.project_name: dist
+        for dist in Virtualenv(pip.venv_dir).iter_distributions(rescan=True)
+    }
+
+    # N.B.: We avoid testing the full version (local segment) since our vendored Pip is
+    # 20.3.4+patched. Testing the release (`<major>.<minor>.<patch>`) gets us the assurance we want
+    # here.
+    assert (
+        version.version.parsed_version.release
+        == dists_by_project_name.pop(ProjectName("pip")).metadata.version.parsed_version.release
+    )
+
+    return dists_by_project_name
+
+
+@applicable_pip_versions
+def test_extra_pip_requirements_setuptools_override(
+    create_pip,  # type: CreatePip
+    version,  # type: PipVersionValue
+    current_interpreter,  # type: PythonInterpreter
+):
+    # type: (...) -> None
+
+    # N.B.: 44.0.0 is the oldest wheel version used by any of our supported `--pip-version`s.
+    custom_setuptools_version = Version("43.0.0")
+    custom_setuptools_requirement = "setuptools=={version}".format(
+        version=custom_setuptools_version
+    )
+
+    if PipVersion.VENDORED is version:
+        with pytest.raises(
+            ValueError,
+            match=re.escape(
+                "An `--extra-pip-requirement` cannot be used to override the setuptools version "
+                "for vendored Pip. If you need a custom setuptools you need to use `--pip-version` "
+                "to select a non-vendored Pip version. Given: {setuptools_requirement}".format(
+                    setuptools_requirement=custom_setuptools_requirement
+                )
+            ),
+        ):
+            create_pip(
+                current_interpreter,
+                version=version,
+                extra_requirements=[Requirement.parse(custom_setuptools_requirement)],
+            )
+        return
+
+    dists_by_project_name = index_pip_distributions(
+        create_pip, current_interpreter, version, custom_setuptools_requirement
+    )
+    assert dists_by_project_name.pop(ProjectName("wheel")) in version.wheel_requirement
+
+    setuptools = dists_by_project_name.pop(ProjectName("setuptools"))
+    assert setuptools not in version.setuptools_requirement
+    assert custom_setuptools_version == setuptools.metadata.version
+
+
+@applicable_pip_versions
+def test_extra_pip_requirements_wheel_override(
+    create_pip,  # type: CreatePip
+    version,  # type: PipVersionValue
+    current_interpreter,  # type: PythonInterpreter
+):
+    # type: (...) -> None
+
+    # N.B.: 0.37.1 is the oldest wheel version used by any of our supported `--pip-version`s.
+    custom_wheel_version = Version("0.37.0")
+    custom_wheel_requirement = "wheel=={version}".format(version=custom_wheel_version)
+
+    if PipVersion.VENDORED is version:
+        with pytest.raises(
+            ValueError,
+            match=re.escape(
+                "An `--extra-pip-requirement` cannot be used to override the wheel version "
+                "for vendored Pip. If you need a custom wheel version you need to use "
+                "`--pip-version` to select a non-vendored Pip version. "
+                "Given: {wheel_requirement}".format(wheel_requirement=custom_wheel_requirement)
+            ),
+        ):
+            create_pip(
+                current_interpreter,
+                version=version,
+                extra_requirements=[Requirement.parse(custom_wheel_requirement)],
+            )
+        return
+
+    dists_by_project_name = index_pip_distributions(
+        create_pip, current_interpreter, version, custom_wheel_requirement
+    )
+    assert dists_by_project_name.pop(ProjectName("setuptools")) in version.setuptools_requirement
+
+    wheel = dists_by_project_name.pop(ProjectName("wheel"))
+    assert wheel not in version.wheel_requirement
+    assert custom_wheel_version == wheel.metadata.version
diff --git a/tests/tools/commands/test_repository.py b/tests/tools/commands/test_repository.py
index a164fd9a7..5e09946ce 100644
--- a/tests/tools/commands/test_repository.py
+++ b/tests/tools/commands/test_repository.py
@@ -221,7 +221,7 @@ def test_extract_lifecycle(pex, pex_tools_env, tmpdir):
     vendored_pip_dists_dir = os.path.join(str(tmpdir), "vendored-pip-dists")
     get_pip(resolver=ConfiguredResolver.default()).spawn_download_distributions(
         download_dir=vendored_pip_dists_dir,
-        requirements=[PipVersion.VENDORED.wheel_requirement],
+        requirements=[str(PipVersion.VENDORED.wheel_requirement)],
         build_configuration=BuildConfiguration.create(allow_builds=False),
     ).wait()