diff --git a/devel/py-grpcio/Makefile b/devel/py-grpcio/Makefile
index 15a6fb43573c..b3917063242b 100644
--- a/devel/py-grpcio/Makefile
+++ b/devel/py-grpcio/Makefile
@@ -1,31 +1,31 @@
 PORTNAME=	grpcio
-PORTVERSION=	1.57.0
+PORTVERSION=	1.58.0
 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
 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 bc0509ce86f1..5cc057cd744b 100644
--- a/devel/py-grpcio/distinfo
+++ b/devel/py-grpcio/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1691904681
-SHA256 (grpcio-1.57.0.tar.gz) = 4b089f7ad1eb00a104078bab8015b0ed0ebcb3b589e527ab009c53893fd4e613
-SIZE (grpcio-1.57.0.tar.gz) = 24737546
+TIMESTAMP = 1694182572
+SHA256 (grpcio-1.58.0.tar.gz) = 532410c51ccd851b706d1fbc00a87be0f5312bd6f8e5dbf89d4e99c7f79d7499
+SIZE (grpcio-1.58.0.tar.gz) = 24784339
diff --git a/devel/py-grpcio/files/patch-third__party_abseil-cpp_absl_base_internal_sysinfo.cc b/devel/py-grpcio/files/patch-third__party_abseil-cpp_absl_base_internal_sysinfo.cc
new file mode 100644
index 000000000000..1eb995321143
--- /dev/null
+++ b/devel/py-grpcio/files/patch-third__party_abseil-cpp_absl_base_internal_sysinfo.cc
@@ -0,0 +1,33 @@
+--- third_party/abseil-cpp/absl/base/internal/sysinfo.cc.orig	2023-09-08 14:23:50 UTC
++++ third_party/abseil-cpp/absl/base/internal/sysinfo.cc
+@@ -34,6 +34,10 @@
+ #include <sys/sysctl.h>
+ #endif
+ 
++#ifdef __FreeBSD__
++#include <pthread_np.h>
++#endif
++
+ #if defined(__myriad2__)
+ #include <rtems.h>
+ #endif
+@@ -421,14 +425,18 @@ pid_t GetTID() {
+   return tid;
+ }
+ 
+-#elif defined(__APPLE__)
++#elif defined(__APPLE__) || defined(__FreeBSD__)
+ 
+ pid_t GetTID() {
+   uint64_t tid;
+   // `nullptr` here implies this thread.  This only fails if the specified
+   // thread is invalid or the pointer-to-tid is null, so we needn't worry about
+   // it.
++#if __FreeBSD__
++  tid = pthread_getthreadid_np();
++#else
+   pthread_threadid_np(nullptr, &tid);
++#endif
+   return static_cast<pid_t>(tid);
+ }
+ 
diff --git a/devel/py-grpcio/files/patch-third__party_abseil-cpp_absl_time_internal_cctz_src_time__zone__format.cc b/devel/py-grpcio/files/patch-third__party_abseil-cpp_absl_time_internal_cctz_src_time__zone__format.cc
new file mode 100644
index 000000000000..e104a9b365cd
--- /dev/null
+++ b/devel/py-grpcio/files/patch-third__party_abseil-cpp_absl_time_internal_cctz_src_time__zone__format.cc
@@ -0,0 +1,11 @@
+--- third_party/abseil-cpp/absl/time/internal/cctz/src/time_zone_format.cc.orig	2023-09-08 14:26:05 UTC
++++ third_party/abseil-cpp/absl/time/internal/cctz/src/time_zone_format.cc
+@@ -19,7 +19,7 @@
+ #endif
+ 
+ #if defined(HAS_STRPTIME) && HAS_STRPTIME
+-#if !defined(_XOPEN_SOURCE) && !defined(__OpenBSD__)
++#if !defined(_XOPEN_SOURCE) && !defined(__OpenBSD__) && !defined(__FreeBSD__)
+ #define _XOPEN_SOURCE 500  // Exposes definitions for SUSv2 (UNIX 98).
+ #endif
+ #endif
diff --git a/devel/py-grpcio/files/patch-third__party_boringssl-with-bazel_src_include_openssl_base.h b/devel/py-grpcio/files/patch-third__party_boringssl-with-bazel_src_include_openssl_base.h
index c500bed72df1..94e724e94c7e 100644
--- a/devel/py-grpcio/files/patch-third__party_boringssl-with-bazel_src_include_openssl_base.h
+++ b/devel/py-grpcio/files/patch-third__party_boringssl-with-bazel_src_include_openssl_base.h
@@ -1,12 +1,12 @@
---- third_party/boringssl-with-bazel/src/include/openssl/base.h.orig	2022-05-03 21:27:37 UTC
+--- third_party/boringssl-with-bazel/src/include/openssl/base.h.orig	2023-09-06 01:32:08 UTC
 +++ third_party/boringssl-with-bazel/src/include/openssl/base.h
-@@ -483,9 +483,6 @@ typedef void *OPENSSL_BLOCK;
+@@ -413,9 +413,6 @@ typedef void *OPENSSL_BLOCK;
  // MSVC doesn't set __cplusplus to 201103 to indicate C++11 support (see
  // https://connect.microsoft.com/VisualStudio/feedback/details/763051/a-value-of-predefined-macro-cplusplus-is-still-199711l)
  // so MSVC is just assumed to support C++11.
 -#if !defined(BORINGSSL_NO_CXX) && __cplusplus < 201103L && !defined(_MSC_VER)
 -#define BORINGSSL_NO_CXX
 -#endif
  
  #if !defined(BORINGSSL_NO_CXX)