diff --git a/devel/py-virtualenv/Makefile b/devel/py-virtualenv/Makefile
index 5aca8680eb08..d4ed24acace4 100644
--- a/devel/py-virtualenv/Makefile
+++ b/devel/py-virtualenv/Makefile
@@ -1,75 +1,76 @@
 PORTNAME=	virtualenv
-PORTVERSION=	20.24.7
+PORTVERSION=	20.25.0
 CATEGORIES=	devel python
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	nivit@FreeBSD.org
 COMMENT=	Tool for creating isolated Python environments
 WWW=		https://virtualenv.pypa.io
 
 LICENSE=	MIT
 
-BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}distlib>=0.3.6:devel/py-distlib@${PY_FLAVOR} \
+BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}distlib>=0.3.7:devel/py-distlib@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}hatch-vcs>=0.3:devel/py-hatch-vcs@${PY_FLAVOR}
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}distlib>=0.3.6:devel/py-distlib@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}filelock>=3.4.1:sysutils/py-filelock@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}platformdirs>=2.4:devel/py-platformdirs@${PY_FLAVOR}
+RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}distlib>=0.3.7:devel/py-distlib@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}filelock>=3.12.2:sysutils/py-filelock@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}platformdirs>=3.9.1:devel/py-platformdirs@${PY_FLAVOR}
 # tests: 296 passed, 26 skipped
-TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}covdefaults>=2.2.2:devel/py-covdefaults@${PY_FLAVOR} \
+TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}covdefaults>=2.3:devel/py-covdefaults@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}coverage_enable_subprocess>=1.0:devel/py-coverage_enable_subprocess@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}flaky>=3.7.0:devel/py-flaky@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}packaging>=21.3:devel/py-packaging@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}packaging>=23.1:devel/py-packaging@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-env>=0.6.2:devel/py-pytest-env@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pytest-mock>0:devel/py-pytest-mock@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pytest-randomly>=3.10.3:devel/py-pytest-randomly@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pytest-mock>=3.10:devel/py-pytest-mock@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pytest-randomly>=3.12:devel/py-pytest-randomly@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-timeout>=2.1.0:devel/py-pytest-timeout@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}time-machine>=2.10.0:devel/py-time-machine@${PY_FLAVOR}
 
 USES=		cpe python
 USE_GITHUB=	yes
 GH_ACCOUNT=	pypa
 USE_PYTHON=	autoplist concurrent pep517 pytest
 
 # Fix the LookupError: setuptools-scm was unable to detect version (build target)
 MAKE_ENV=	SETUPTOOLS_SCM_PRETEND_VERSION="${PORTVERSION}"
 
 .if make(test)
 TEST_ENV=	PYTHONIOENCODING=utf-8 \
 		PYTHONPATH="${STAGEDIR}${PYTHON_SITELIBDIR}"
 .endif
 
 NO_ARCH=	yes
 
 OPTIONS_DEFINE=	DOCS
 
-DOCS_BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}click-default-group>0:devel/py-click-default-group@${PY_FLAVOR} \
-			${PYTHON_PKGNAMEPREFIX}filelock>0:sysutils/py-filelock@${PY_FLAVOR} \
-			${PYTHON_PKGNAMEPREFIX}furo>=2022.12.7:textproc/py-furo@${PY_FLAVOR} \
-			${PYTHON_PKGNAMEPREFIX}platformdirs>0:devel/py-platformdirs@${PY_FLAVOR} \
-			${PYTHON_PKGNAMEPREFIX}proselint>0:devel/py-proselint@${PY_FLAVOR} \
-			${PYTHON_PKGNAMEPREFIX}sphinx-argparse>0:textproc/py-sphinx-argparse@${PY_FLAVOR} \
+DOCS_BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}click-default-group>=1.2.4:devel/py-click-default-group@${PY_FLAVOR} \
+			${PYTHON_PKGNAMEPREFIX}filelock>=3.12.2:sysutils/py-filelock@${PY_FLAVOR} \
+			${PYTHON_PKGNAMEPREFIX}furo>=2023.7.26:textproc/py-furo@${PY_FLAVOR} \
+			${PYTHON_PKGNAMEPREFIX}platformdirs>3.9.1:devel/py-platformdirs@${PY_FLAVOR} \
+			${PYTHON_PKGNAMEPREFIX}proselint>=0.13:devel/py-proselint@${PY_FLAVOR} \
+			${PYTHON_PKGNAMEPREFIX}sphinx-argparse>=0.4:textproc/py-sphinx-argparse@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}sphinx>=1.8.0,1:textproc/py-sphinx@${PY_FLAVOR} \
+			${PYTHON_PKGNAMEPREFIX}sphinxcontrib-towncrier>=0.3.2a0:textproc/py-sphinxcontrib-towncrier@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}towncrier>=22.8.0:textproc/py-towncrier@${PY_FLAVOR}
 DOCS_BINARY_ALIAS=	towncrier=towncrier-${PYTHON_VER}
 DOCS_PLIST_FILES=	man/man1/virtualenv.1.gz
 DOCS_PORTDOCS=		* .buildinfo
 
 # Fix the Exception:
 #
 # File "/build/lib/virtualenv/run/plugin/discovery.py", line 20, in get_discover
 #    default=next(iter(choices)),
 # StopIteration
 #
 # Apparently it doesn't work setting PYTHONPATH environment variable...
 VIRTUALENV_WHEEL=	${WRKSRC}/dist/${PORTNAME}-${PORTVERSION}-py${PYTHON_MAJOR_VER}-none-any.whl
 
 post-patch:
 	@${SED} -i.bak -e 's,%%VIRTUALENV_WHEEL%%,${VIRTUALENV_WHEEL},1' \
 	-e 's,%%PYTHON_VER%%,${PYTHON_VER},1' \
 	${WRKSRC}/docs/conf.py
 
 post-install-DOCS-on:
 	${LOCALBASE}/bin/sphinx-build-${PYTHON_VER} -d ${WRKDIR} -b html -n ${WRKSRC}/docs ${STAGEDIR}${DOCSDIR}
 	${LOCALBASE}/bin/sphinx-build-${PYTHON_VER} -d ${WRKDIR} -b man -n ${WRKSRC}/docs ${STAGEDIR}${MANPREFIX}/man/man1
 
 .include <bsd.port.mk>
diff --git a/devel/py-virtualenv/distinfo b/devel/py-virtualenv/distinfo
index b8386043931f..269fe9f70f4c 100644
--- a/devel/py-virtualenv/distinfo
+++ b/devel/py-virtualenv/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1700600662
-SHA256 (pypa-virtualenv-20.24.7_GH0.tar.gz) = 163ab7db5cfecceab7647509fadd42e1f953b56ae364fef3b6a3792ad0ccebbc
-SIZE (pypa-virtualenv-20.24.7_GH0.tar.gz) = 7182046
+TIMESTAMP = 1701448402
+SHA256 (pypa-virtualenv-20.25.0_GH0.tar.gz) = c4ccb63405aab372d7708d9a25071f35b6f091b17505496573fc76cb98632392
+SIZE (pypa-virtualenv-20.25.0_GH0.tar.gz) = 7191384