diff --git a/devel/py-grpcio/Makefile b/devel/py-grpcio/Makefile
index 7c01b2d7aa84..476a29288cfd 100644
--- a/devel/py-grpcio/Makefile
+++ b/devel/py-grpcio/Makefile
@@ -1,33 +1,33 @@
 PORTNAME=	grpcio
-PORTVERSION=	1.66.0
+PORTVERSION=	1.66.2
 CATEGORIES=	devel python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	vanilla@FreeBSD.org
 COMMENT=	HTTP/2-based RPC framework
 WWW=		https://pypi.org/project/grpcio/
 
 LICENSE=	APACHE20
 
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}protobuf>=3:devel/py-protobuf@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}six>1:devel/py-six@${PY_FLAVOR}
 LIB_DEPENDS=	libcares.so:dns/c-ares
 
 USES=		compiler:c++11-lib localbase:ldflags python ssl
 BROKEN_SSL=	libressl
 BROKEN_SSL_REASON=	use of undeclared identifier 'X509_STORE_set_get_crl'
 USE_PYTHON=	autoplist cython distutils
 MAKE_ENV+=	GRPC_PYTHON_BUILD_SYSTEM_CARES=true \
 		GRPC_PYTHON_BUILD_SYSTEM_OPENSSL=true \
 		GRPC_PYTHON_BUILD_SYSTEM_ZLIB=true
 LDFLAGS+=	-lcares
 
 post-patch:
 	@${RM} ${WRKSRC}/src/python/grpcio/grpc/_cython/cygrpc.cpp
 
 post-install:
 	${STRIP_CMD} ${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}/grpc/_cython/cygrpc*.so
 	${REINPLACE_CMD} -e 's|^.*so$$|${PYTHONPREFIX_SITELIBDIR}/grpc/_cython/cygrpc${PYTHON_EXT_SUFFIX}.so|' ${_PYTHONPKGLIST}
 
 .include <bsd.port.mk>
diff --git a/devel/py-grpcio/distinfo b/devel/py-grpcio/distinfo
index 2ea46228b3c7..04caf3104a4d 100644
--- a/devel/py-grpcio/distinfo
+++ b/devel/py-grpcio/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1724407658
-SHA256 (grpcio-1.66.0.tar.gz) = c1ea4c528e7db6660718e4165fd1b5ac24b79a70c870a7bc0b7bdb9babab7c1e
-SIZE (grpcio-1.66.0.tar.gz) = 12347554
+TIMESTAMP = 1728398525
+SHA256 (grpcio-1.66.2.tar.gz) = 563588c587b75c34b928bc428548e5b00ea38c46972181a4d8b75ba7e3f24231
+SIZE (grpcio-1.66.2.tar.gz) = 12489713