diff --git a/devel/py-monkeytype/Makefile b/devel/py-monkeytype/Makefile
index a90b32fadc8d..a9834aa2a88b 100644
--- a/devel/py-monkeytype/Makefile
+++ b/devel/py-monkeytype/Makefile
@@ -1,23 +1,23 @@
 # Created by: Po-Chuan Hsieh <sunpoet@FreeBSD.org>
 
 PORTNAME=	monkeytype
-PORTVERSION=	20.5.0
+PORTVERSION=	21.5.0
 CATEGORIES=	devel python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTNAME=	MonkeyType-${PORTVERSION}
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Generate type annotations from sampled production types
 
 LICENSE=	BSD3CLAUSE
 
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}libcst>=0.3.5:devel/py-libcst@${PY_FLAVOR} \
+RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}libcst>=0.3.7:devel/py-libcst@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}mypy_extensions>=0:devel/py-mypy_extensions@${PY_FLAVOR}
 
 USES=		python:3.6+
 USE_PYTHON=	autoplist concurrent distutils
 
 NO_ARCH=	yes
 
 .include <bsd.port.mk>
diff --git a/devel/py-monkeytype/distinfo b/devel/py-monkeytype/distinfo
index a53c64b6d514..26685d46ff89 100644
--- a/devel/py-monkeytype/distinfo
+++ b/devel/py-monkeytype/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1605426419
-SHA256 (MonkeyType-20.5.0.tar.gz) = fe596bebc5e1b6a64eae71a40b880688de433e4f70507a31ada48510195251dd
-SIZE (MonkeyType-20.5.0.tar.gz) = 30561
+TIMESTAMP = 1624189725
+SHA256 (MonkeyType-21.5.0.tar.gz) = e47089f032e65f9bc7b4146725285837b75136f28e3025b434d494f6d1b3cb87
+SIZE (MonkeyType-21.5.0.tar.gz) = 32640