diff --git a/devel/py-tox/Makefile b/devel/py-tox/Makefile
index 8c3113cf9042..d847a9e66016 100644
--- a/devel/py-tox/Makefile
+++ b/devel/py-tox/Makefile
@@ -1,41 +1,41 @@
 PORTNAME=	tox
-DISTVERSION=	4.20.0
+DISTVERSION=	4.21.0
 CATEGORIES=	devel python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	bofh@FreeBSD.org
 COMMENT=	Virtualenv-based automation of test activities
 WWW=		https://tox.readthedocs.org/
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}hatch-vcs>=0.4:devel/py-hatch-vcs@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}hatchling>=1.21:devel/py-hatchling@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}cachetools>=5.3.2:devel/py-cachetools@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}chardet>=5.2:textproc/py-chardet@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}colorama>=0.4.6:devel/py-colorama@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}filelock>=3.13.1:sysutils/py-filelock@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}packaging>=23.2:devel/py-packaging@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}platformdirs>=4.1:devel/py-platformdirs@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pluggy>=1.3:devel/py-pluggy@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pyproject_api>=1.6.1:devel/py-pyproject-api@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}virtualenv>=20.25:devel/py-virtualenv@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	autoplist concurrent pep517
 
 NO_ARCH=	yes
 
 .include <bsd.port.pre.mk>
 
 .if ${PYTHON_REL} < 31100
 RUN_DEPENDS+=	${PY_TOMLI}
 .endif
 
 # tox.ini clobbers our pytest arguments
 post-extract:
 	${RM} ${WRKSRC}/tox.ini
 
 .include <bsd.port.post.mk>
diff --git a/devel/py-tox/distinfo b/devel/py-tox/distinfo
index de78b7a66793..15b882974df3 100644
--- a/devel/py-tox/distinfo
+++ b/devel/py-tox/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1727897115
-SHA256 (tox-4.20.0.tar.gz) = 5b78a49b6eaaeab3ae4186415e7c97d524f762ae967c63562687c3e5f0ec23d5
-SIZE (tox-4.20.0.tar.gz) = 181364
+TIMESTAMP = 1728023892
+SHA256 (tox-4.21.0.tar.gz) = e64dd9847ff3a7ec90368be412d7efe61a39caf043222ffbe9ad638ea435f6f6
+SIZE (tox-4.21.0.tar.gz) = 187638