diff --git a/devel/py-setuptools/Makefile b/devel/py-setuptools/Makefile
--- a/devel/py-setuptools/Makefile
+++ b/devel/py-setuptools/Makefile
@@ -1,14 +1,13 @@
 PORTNAME=	setuptools
-PORTVERSION=	63.1.0
-PORTREVISION=	2
+DISTVERSION=	75.3.2
 CATEGORIES=	devel python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DIST_SUBDIR=	python
 
-# note: before committing to this port, contact portmgr to arrange for an
-# experimental ports run.  Untested commits may be backed out at portmgr's
-# discretion.
+# note: before committing a new major version, contact portmgr to
+# arrange for an experimental ports run. Untested commits may be
+# backed out.
 MAINTAINER=	python@FreeBSD.org
 COMMENT=	Python packages installer
 WWW=		https://pypi.org/project/setuptools/
@@ -16,33 +15,49 @@
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
-USES=		cpe python
-USE_PYTHON=	allflavors autoplist concurrent distutils
+BUILD_DEPENDS=	${_CORE_DEPENDS}
+RUN_DEPENDS=	${_CORE_DEPENDS}
 
+USES=		cpe python
 CPE_VENDOR=	python
+USE_PYTHON=	allflavors autoplist concurrent pep517 pytest
+
+_CORE_DEPENDS=	${PYTHON_PKGNAMEPREFIX}packaging>=24:devel/py-packaging@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}more-itertools>=8.8:devel/py-more-itertools@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}wheel>=0.43.0:devel/py-wheel@${PY_FLAVOR}
+
+# circular dependencies
+#_CORE_DEPENDS=	${PYTHON_PKGNAMEPREFIX}jaraco.text>=3.7:devel/py-jaraco.text@${PY_FLAVOR} \
+#		${PYTHON_PKGNAMEPREFIX}platformdirs>=4.2.2:devel/py-platformdirs@${PY_FLAVOR} \
+#		${PYTHON_PKGNAMEPREFIX}jaraco.collections>0:devel/py-jaraco.collections@${PY_FLAVOR} \
+#		${PYTHON_PKGNAMEPREFIX}jaraco.functools>=4:devel/py-jaraco.functools@${PY_FLAVOR} \
+#		${PYTHON_PKGNAMEPREFIX}ruff>=0.7.0:devel/py-ruff@${PY_FLAVOR}
+
+# in devel/py-jaraco.text dependency chain via devel/py-inflect
+_CORE_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}typing-extensions>0:devel/py-typing-extensions@${PY_FLAVOR}
+
+# remove vendored packages of those already installed via pkg(8)
+_DIST_EXCLUDES=	packaging* \
+		more_itertools* \
+		wheel* \
+		importlib_metadata* \
+		tomli* \
+		typing_extensions* \
+		zipp*
+EXTRACT_AFTER_ARGS=	${_DIST_EXCLUDES:S,^,--exclude setuptools/_vendor/,}
 
-MAKE_ENV+=	SETUPTOOLS_DISABLE_VERSIONED_EASY_INSTALL_SCRIPT=1
 NO_ARCH=	yes
-PYDISTUTILS_SETUP=	${PYSETUP}
-
-PLIST_FILES=	"@sample %%PYTHON_SITELIBDIR%%/easy-install.pth.dist %%PYTHON_SITELIBDIR%%/easy-install.pth"
 
 .include <bsd.port.pre.mk>
 
-.if ${FLAVOR} != ${FLAVORS:[1]}
-SUB_FILES+=	pkg-message
-SUB_LIST+=	PYTHON_VER=${PYTHON_VER}
+.if ${PYTHON_REL} < 30900
+_CORE_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}importlib-resources>=5.10.2:devel/py-importlib-resources@${PY_FLAVOR}
+.endif
+.if ${PYTHON_REL} < 31000
+_CORE_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}importlib-metadata>=6:devel/py-importlib-metadata@${PY_FLAVOR}
+.endif
+.if ${PYTHON_REL} < 31100
+_CORE_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}tomli>=2.0.1:textproc/py-tomli@${PY_FLAVOR}
 .endif
-
-# These create dependency loops in redports/poudriere, because setuptools
-# is currently an explicit BUILD & RUN dependency in Uses/python.mk.
-#TEST_DEPENDS=  ${PYTHON_PKGNAMEPREFIX}pytest>0:devel/py-pytest@${PY_FLAVOR}
-# pkg install -y py38-pytest py38-mock py38-pytest-fixture-config py38-pytest-virtualenv py38-paver
-
-post-install:
-	${INSTALL_DATA} ${FILESDIR}/easy-install.pth.dist ${STAGEDIR}${PYTHON_SITELIBDIR}/
-
-do-test:
-	cd ${WRKSRC} && ${PYTHON_CMD} -m pytest -v -rs
 
 .include <bsd.port.post.mk>
diff --git a/devel/py-setuptools/distinfo b/devel/py-setuptools/distinfo
--- a/devel/py-setuptools/distinfo
+++ b/devel/py-setuptools/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1657634036
-SHA256 (python/setuptools-63.1.0.tar.gz) = 16923d366ced322712c71ccb97164d07472abeecd13f3a6c283f6d5d26722793
-SIZE (python/setuptools-63.1.0.tar.gz) = 2599380
+TIMESTAMP = 1742583941
+SHA256 (python/setuptools-75.3.2.tar.gz) = 3c1383e1038b68556a382c1e8ded8887cd20141b0eb5708a6c8d277de49364f5
+SIZE (python/setuptools-75.3.2.tar.gz) = 1354489
diff --git a/devel/py-setuptools/files/easy-install.pth.dist b/devel/py-setuptools/files/easy-install.pth.dist
deleted file mode 100644
--- a/devel/py-setuptools/files/easy-install.pth.dist
+++ /dev/null
@@ -1,2 +0,0 @@
-import sys; sys.__plen = len(sys.path)
-import sys; new=sys.path[sys.__plen:]; del sys.path[sys.__plen:]; p=getattr(sys,'__egginsert',0); sys.path[p:p]=new; sys.__egginsert = p+len(new)
diff --git a/devel/py-setuptools/files/patch-setuptools_package__index.py b/devel/py-setuptools/files/patch-setuptools_package__index.py
deleted file mode 100644
--- a/devel/py-setuptools/files/patch-setuptools_package__index.py
+++ /dev/null
@@ -1,11 +0,0 @@
---- setuptools/package_index.py.orig	2022-07-04 02:25:25 UTC
-+++ setuptools/package_index.py
-@@ -197,7 +197,7 @@ def unique_values(func):
-     return wrapper
- 
- 
--REL = re.compile(r"""<([^>]*\srel\s*=\s*['"]?([^'">]+)[^>]*)>""", re.I)
-+REL = re.compile(r"""<([^>]*\srel\s{0,10}=\s{0,10}['"]?([^'" >]+)[^>]*)>""", re.I)
- # this line is here to fix emacs' cruddy broken syntax highlighting
- 
- 
diff --git a/devel/py-setuptools/files/pkg-message.in b/devel/py-setuptools/files/pkg-message.in
deleted file mode 100644
--- a/devel/py-setuptools/files/pkg-message.in
+++ /dev/null
@@ -1,8 +0,0 @@
-[
-{ type: install
-  message: <<EOM
-  Only %%PREFIX%%/bin/easy_install-%%PYTHON_VER%% script has been installed
-  since Python %%PYTHON_VER%% is not the default Python version.
-EOM
-}
-]