diff --git a/net/py-portend/Makefile b/net/py-portend/Makefile
index e36fcf8067d7..78acb5998cef 100644
--- a/net/py-portend/Makefile
+++ b/net/py-portend/Makefile
@@ -1,28 +1,25 @@
 PORTNAME=	portend
-PORTVERSION=	2.5
-PORTREVISION=	2
+PORTVERSION=	3.2.1
 CATEGORIES=	net python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	k@stereochro.me
 COMMENT=	Monitors TCP ports for bound or unbound states
 WWW=		https://github.com/jaraco/portend
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
-BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools-scm>=1.15.0:devel/py-setuptools-scm@${PY_FLAVOR}
+BUILD_DEPENDS=	${PY_SETUPTOOLS} \
+		${PYTHON_PKGNAMEPREFIX}coherent.licensed>=0:devel/py-coherent.licensed@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}setuptools-scm>=3.4.1:devel/py-setuptools-scm@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}tempora>=1.8:devel/py-tempora@${PY_FLAVOR}
-TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pytest>=3.5:devel/py-pytest@${PY_FLAVOR}
 
 USES=		python
-USE_PYTHON=	autoplist concurrent distutils
+USE_PYTHON=	autoplist concurrent pep517 pytest
 
 NO_ARCH=	yes
 
-# Ignore non-compulsory dependencies (flake8, etc.) from pytest.ini via "-o"
-do-test:
-	@cd ${WRKSRC} && ${PYTHON_CMD} -m pytest -rs -v -o addopts=''
-
 .include <bsd.port.mk>
diff --git a/net/py-portend/distinfo b/net/py-portend/distinfo
index a98651450351..c93ea753a2f2 100644
--- a/net/py-portend/distinfo
+++ b/net/py-portend/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1571548268
-SHA256 (portend-2.5.tar.gz) = 19dc27bfb3c72471bd30a235a4d5fbefef8a7e31cab367744b5d87a205e7bfd9
-SIZE (portend-2.5.tar.gz) = 12237
+TIMESTAMP = 1789685652
+SHA256 (portend-3.2.1.tar.gz) = aa9d40ab1f9e14bdb7d401f42210df35d017c9b97991baeb18568cedfb8c6489
+SIZE (portend-3.2.1.tar.gz) = 12243
diff --git a/net/py-portend/files/patch-portend.py b/net/py-portend/files/patch-portend.py
new file mode 100644
index 000000000000..8d7f0e089dd3
--- /dev/null
+++ b/net/py-portend/files/patch-portend.py
@@ -0,0 +1,11 @@
+--- portend.py.orig	2026-09-18 00:11:34 UTC
++++ portend.py
+@@ -65,7 +65,7 @@ class Checker:
+         """
+         if port is None and isinstance(host, abc.Sequence):
+             host, port = host[:2]
+-        if platform.system() == 'Windows':
++        if platform.system() == 'Windows' or platform.system() == 'FreeBSD':
+             host = client_host(host)  # pragma: nocover
+         info = socket.getaddrinfo(host, port, socket.AF_UNSPEC, socket.SOCK_STREAM)
+         list(itertools.starmap(self._connect, info))
diff --git a/net/py-portend/files/patch-pyproject.toml b/net/py-portend/files/patch-pyproject.toml
new file mode 100644
index 000000000000..e9fb8d7f6840
--- /dev/null
+++ b/net/py-portend/files/patch-pyproject.toml
@@ -0,0 +1,19 @@
+--- pyproject.toml.orig	2025-05-29 20:27:20 UTC
++++ pyproject.toml
+@@ -1,6 +1,6 @@ requires = [
+ [build-system]
+ requires = [
+-	"setuptools>=77",
++	"setuptools",
+ 	"setuptools_scm[toml]>=3.4.1",
+ 	# jaraco/skeleton#174
+ 	"coherent.licensed",
+@@ -21,7 +21,7 @@ requires-python = ">=3.9"
+ 	"Programming Language :: Python :: 3 :: Only",
+ ]
+ requires-python = ">=3.9"
+-license = "MIT"
++license = { text = "MIT" }
+ dependencies = [
+ 	"tempora>=1.8",
+ ]