diff --git a/devel/py-monkeytype/Makefile b/devel/py-monkeytype/Makefile
index 1ad4132c0ee4..5789e251e97e 100644
--- a/devel/py-monkeytype/Makefile
+++ b/devel/py-monkeytype/Makefile
@@ -2,7 +2,7 @@
 # $FreeBSD$
 
 PORTNAME=	monkeytype
-PORTVERSION=	19.11.2
+PORTVERSION=	20.5.0
 CATEGORIES=	devel python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
@@ -13,12 +13,11 @@ COMMENT=	Generate type annotations from sampled production types
 
 LICENSE=	BSD3CLAUSE
 
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}mypy_extensions>=0:devel/py-mypy_extensions@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}retype>=0:devel/py-retype@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}stringcase>=0:devel/py-stringcase@${PY_FLAVOR}
+RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}libcst>=0.3.5:devel/py-libcst@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}mypy_extensions>=0:devel/py-mypy_extensions@${PY_FLAVOR}
 
 USES=		python:3.6+
-USE_PYTHON=	autoplist distutils
+USE_PYTHON=	autoplist concurrent distutils
 
 NO_ARCH=	yes
 
diff --git a/devel/py-monkeytype/distinfo b/devel/py-monkeytype/distinfo
index efd8e2b13e17..a53c64b6d514 100644
--- a/devel/py-monkeytype/distinfo
+++ b/devel/py-monkeytype/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1579339393
-SHA256 (MonkeyType-19.11.2.tar.gz) = 9f052b42851bc24603836ce3105166c8cc5edabeb25e8fcf256fa25777122618
-SIZE (MonkeyType-19.11.2.tar.gz) = 31099
+TIMESTAMP = 1605426419
+SHA256 (MonkeyType-20.5.0.tar.gz) = fe596bebc5e1b6a64eae71a40b880688de433e4f70507a31ada48510195251dd
+SIZE (MonkeyType-20.5.0.tar.gz) = 30561