diff --git a/devel/py-boolean.py/Makefile b/devel/py-boolean.py/Makefile
index 5a34597cf697..395db551858a 100644
--- a/devel/py-boolean.py/Makefile
+++ b/devel/py-boolean.py/Makefile
@@ -1,31 +1,41 @@
 PORTNAME=	boolean.py
-DISTVERSION=	4.0
-PORTREVISION=	1
+DISTVERSION=	5.0
 CATEGORIES=	devel python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
+DISTNAME=	${PORTNAME:C/[-_.]+/_/g}-${DISTVERSION}
 
 MAINTAINER=	kai@FreeBSD.org
 COMMENT=	Create and parse boolean expressions and create custom boolean DSL
 WWW=		https://github.com/bastikr/boolean.py
 
 LICENSE=	BSD2CLAUSE
 LICENSE_FILE=	${WRKSRC}/LICENSE.txt
 
+BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools>=0:devel/py-setuptools@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR}
+TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pytest-xdist>=2:devel/py-pytest-xdist@${PY_FLAVOR}
+
 USES=		python
-USE_PYTHON=	autoplist concurrent distutils unittest
+USE_PYTHON=	autoplist concurrent pep517 pytest
+
+TEST_ARGS=	boolean
 
 NO_ARCH=	yes
 PORTDOCS=	*
 
 OPTIONS_DEFINE=	DOCS
-DOCS_BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}sphinx>=0,1:textproc/py-sphinx@${PY_FLAVOR}
-DOCS_VARS=		PYDISTUTILS_BUILD_TARGET+="build_sphinx -a -E"
+DOCS_BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}sphinx>=0,1:textproc/py-sphinx@${PY_FLAVOR} \
+			${PYTHON_PKGNAMEPREFIX}sphinxcontrib-apidoc>=0.3.0:textproc/py-sphinxcontrib-apidoc@${PY_FLAVOR}
+DOCS_USES=	gmake
+
+post-build-DOCS-on:
+	@${GMAKE} -C ${BUILD_WRKSRC}/docs html
 
 post-install-DOCS-on:
 	@${MKDIR} ${STAGEDIR}${DOCSDIR}
-	(cd ${WRKSRC}/build/sphinx/html && \
+	(cd ${BUILD_WRKSRC}/docs/build/html && \
 		${COPYTREE_SHARE} . ${STAGEDIR}${DOCSDIR} \
 			"! -name .buildinfo -and ! -name objects.inv")
 
 .include <bsd.port.mk>
diff --git a/devel/py-boolean.py/distinfo b/devel/py-boolean.py/distinfo
index 26230b32ad53..666594df3fa8 100644
--- a/devel/py-boolean.py/distinfo
+++ b/devel/py-boolean.py/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1671450445
-SHA256 (boolean.py-4.0.tar.gz) = 17b9a181630e43dde1851d42bef546d616d5d9b4480357514597e78b203d06e4
-SIZE (boolean.py-4.0.tar.gz) = 34504
+TIMESTAMP = 1779505187
+SHA256 (boolean_py-5.0.tar.gz) = 60cbc4bad079753721d32649545505362c754e121570ada4658b852a3a318d95
+SIZE (boolean_py-5.0.tar.gz) = 37047