diff --git a/net/rubygem-grpc/Makefile b/net/rubygem-grpc/Makefile
index 22c9533d1023..b47aaad92226 100644
--- a/net/rubygem-grpc/Makefile
+++ b/net/rubygem-grpc/Makefile
@@ -1,28 +1,28 @@
 PORTNAME=	grpc
-PORTVERSION=	1.65.2
+PORTVERSION=	1.66.0
 CATEGORIES=	net rubygems
 MASTER_SITES=	RG
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Ruby implementation of gRPC
 WWW=		https://github.com/grpc/grpc/tree/master/src/ruby
 
 LICENSE=	BSD3CLAUSE
 
 LIB_DEPENDS=	libgrpc.so:devel/grpc
 RUN_DEPENDS=	ca_root_nss>=0:security/ca_root_nss \
 		rubygem-google-protobuf>=3.25<5.0:devel/rubygem-google-protobuf \
 		rubygem-googleapis-common-protos-types>=1.0<2:devel/rubygem-googleapis-common-protos-types
 
 USES=		cpe gem gmake pkgconfig
 
 MAKE_JOBS_UNSAFE=	yes
 
 post-patch:
 	@${RM} ${WRKSRC}/Makefile ${WRKSRC}/.yardopts
 	@${RM} -r ${WRKSRC}/etc ${WRKSRC}/include ${WRKSRC}/third_party ${WRKSRC}/src/boringssl ${WRKSRC}/src/core
 	@${REINPLACE_CMD} -e 's|%%LOCALBASE%%|${LOCALBASE}|' ${WRKSRC}/src/ruby/lib/grpc.rb
 	@${REINPLACE_CMD} -Ee '/s\.files = /s;, "(Makefile|etc|include|third_party|src/boringssl|src/core)[^"]*"\.freeze;;g' ${WRKSRC}/${GEMSPEC}
 	@${REINPLACE_CMD} -e '/s\.files = /s|"\.yardopts"\.freeze, ||' ${WRKSRC}/${GEMSPEC}
 
 .include <bsd.port.mk>
diff --git a/net/rubygem-grpc/distinfo b/net/rubygem-grpc/distinfo
index 556ad09ebd57..de91b28e7f31 100644
--- a/net/rubygem-grpc/distinfo
+++ b/net/rubygem-grpc/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1722085450
-SHA256 (rubygem/grpc-1.65.2.gem) = 9d696e4e742eb1a7f3b3b7a6b3ee1796e4a6a2b009513b5f048df50e823622cc
-SIZE (rubygem/grpc-1.65.2.gem) = 6685184
+TIMESTAMP = 1725560817
+SHA256 (rubygem/grpc-1.66.0.gem) = 16f57873da6712ae7c5a5cffe798ca568ffaa55604efeab6dce26a5f67cc0e0b
+SIZE (rubygem/grpc-1.66.0.gem) = 6721536