diff --git a/devel/py-black/Makefile b/devel/py-black/Makefile
index c50efe0834fa..97c354ee9552 100644
--- a/devel/py-black/Makefile
+++ b/devel/py-black/Makefile
@@ -1,47 +1,49 @@
 PORTNAME=	black
-PORTVERSION=	20.8b1
-PORTREVISION=	1
+PORTVERSION=	21.5b0
 CATEGORIES=	devel python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Uncompromising code formatter
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools_scm>=0:devel/py-setuptools_scm@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}appdirs>=0:devel/py-appdirs@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}click>=7.1.2:devel/py-click@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}mypy_extensions>=0.4.3:devel/py-mypy_extensions@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pathspec>=0.6<1:devel/py-pathspec@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pathspec>=0.8.1<1:devel/py-pathspec@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}regex>=2020.1.8:textproc/py-regex@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}toml>=0.10.1:textproc/py-toml@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}typed-ast>=1.4.0:devel/py-typed-ast@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}typing-extensions>=3.7.4:devel/py-typing-extensions@${PY_FLAVOR}
+		${PYTHON_PKGNAMEPREFIX}toml>=0.10.1:textproc/py-toml@${PY_FLAVOR}
 
 USES=		python:3.6+
 USE_PYTHON=	autoplist concurrent distutils
 
 NO_ARCH=	yes
 
 OPTIONS_DEFINE=	COLORAMA D
 OPTIONS_DEFAULT=COLORAMA
 COLORAMA_DESC=	Color support
 D_DESC=		Blackd HTTP server
 
 COLORAMA_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}colorama>=0.4.3:devel/py-colorama@${PY_FLAVOR}
 D_RUN_DEPENDS=		${PYTHON_PKGNAMEPREFIX}aiohttp>=3.3.2:www/py-aiohttp@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}aiohttp_cors>=0:www/py-aiohttp_cors@${PY_FLAVOR}
 
 .include <bsd.port.pre.mk>
 
 .if ${PYTHON_REL} < 3700
 RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}dataclasses>=0.6:devel/py-dataclasses@${PY_FLAVOR}
 .endif
 
+.if ${PYTHON_REL} < 3800
+RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}typed-ast>=1.4.2:devel/py-typed-ast@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}typing-extensions>=3.7.4:devel/py-typing-extensions@${PY_FLAVOR}
+.endif
+
 do-test:
 	@cd ${WRKSRC} && ${PYTHON_CMD} ${PYDISTUTILS_SETUP} test
 
 .include <bsd.port.post.mk>
diff --git a/devel/py-black/distinfo b/devel/py-black/distinfo
index eff36112c6d2..5ba18fad5c0b 100644
--- a/devel/py-black/distinfo
+++ b/devel/py-black/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1598529368
-SHA256 (black-20.8b1.tar.gz) = 1c02557aa099101b9d21496f8a914e9ed2222ef70336404eeeac8edba836fbea
-SIZE (black-20.8b1.tar.gz) = 1096433
+TIMESTAMP = 1620405391
+SHA256 (black-21.5b0.tar.gz) = 9dc2042018ca10735366d944c2c12d9cad6dec74a3d5f679d09384ea185d9943
+SIZE (black-21.5b0.tar.gz) = 1152691