diff --git a/devel/py-pyupgrade/Makefile b/devel/py-pyupgrade/Makefile
index b59181df5926..3cc19657d5c4 100644
--- a/devel/py-pyupgrade/Makefile
+++ b/devel/py-pyupgrade/Makefile
@@ -1,21 +1,21 @@
 PORTNAME=	pyupgrade
-DISTVERSION=	3.20.0
+DISTVERSION=	3.21.0
 CATEGORIES=	devel
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	bofh@FreeBSD.org
 COMMENT=	Tool to automatically upgrade Python syntax for newer versions
 WWW=		https://github.com/asottile/pyupgrade
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}tokenize-rt>=3.2.0:devel/py-tokenize-rt@${PY_FLAVOR}
+RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}tokenize-rt>=6.1.0:devel/py-tokenize-rt@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	autoplist distutils
 
 NO_ARCH=	yes
 
 .include <bsd.port.mk>
diff --git a/devel/py-pyupgrade/distinfo b/devel/py-pyupgrade/distinfo
index 0ae260424400..816e12e1c680 100644
--- a/devel/py-pyupgrade/distinfo
+++ b/devel/py-pyupgrade/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1748195791
-SHA256 (pyupgrade-3.20.0.tar.gz) = dd6a16c13fc1a7db45796008689a9a35420bd364d681430f640c5e54a3d351ea
-SIZE (pyupgrade-3.20.0.tar.gz) = 45007
+TIMESTAMP = 1760114436
+SHA256 (pyupgrade-3.21.0.tar.gz) = 3e63a882ec1d16f5621736d938952df3cdc2446501fb049e711415cb8d273960
+SIZE (pyupgrade-3.21.0.tar.gz) = 45210