Turns out the -D option of install is GNU-specific, and doesn't exist on MacOS.

Makefile

@@ -144,7 +144,7 @@ LD = $(LD_$(CONFIG))
 LDXX = $(LDXX_$(CONFIG))
 AR = ar
 STRIP = strip --strip-unneeded
-INSTALL = install -D
+INSTALL = install
 RM = rm -f
 
 ifndef VALID_CONFIG_$(CONFIG)
@@ -1930,24 +1930,30 @@ install-headers: install-headers_c install-headers_cxx
 
 install-headers_c:
 	$(E) "[INSTALL] Installing public C headers"
+	$(Q) $(foreach h, $(PUBLIC_HEADERS_C), $(INSTALL) -d $(prefix)/$(dir $(h)) && ) exit 0 || exit 1
 	$(Q) $(foreach h, $(PUBLIC_HEADERS_C), $(INSTALL) $(h) $(prefix)/$(h) && ) exit 0 || exit 1
 
 install-headers_cxx:
 	$(E) "[INSTALL] Installing public C++ headers"
+	$(Q) $(foreach h, $(PUBLIC_HEADERS_CXX), $(INSTALL) -d $(prefix)/$(dir $(h)) && ) exit 0 || exit 1
 	$(Q) $(foreach h, $(PUBLIC_HEADERS_CXX), $(INSTALL) $(h) $(prefix)/$(h) && ) exit 0 || exit 1
 
 install-static: install-static_c install-static_cxx
 
 install-static_c: static_c strip-static_c
 	$(E) "[INSTALL] Installing libgpr.a"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/libgpr.a $(prefix)/lib/libgpr.a
 	$(E) "[INSTALL] Installing libgrpc.a"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/libgrpc.a $(prefix)/lib/libgrpc.a
 	$(E) "[INSTALL] Installing libgrpc_unsecure.a"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/libgrpc_unsecure.a $(prefix)/lib/libgrpc_unsecure.a
 
 install-static_cxx: static_cxx strip-static_cxx
 	$(E) "[INSTALL] Installing libgrpc++.a"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/libgrpc++.a $(prefix)/lib/libgrpc++.a
 
 
@@ -1955,10 +1961,12 @@ install-static_cxx: static_cxx strip-static_cxx
 install-shared_c: shared_c strip-shared_c
 ifeq ($(SYSTEM),MINGW32)
 	$(E) "[INSTALL] Installing gpr.$(SHARED_EXT)"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/gpr.$(SHARED_EXT) $(prefix)/lib/gpr.$(SHARED_EXT)
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/libgpr-imp.a $(prefix)/lib/libgpr-imp.a
 else
 	$(E) "[INSTALL] Installing libgpr.$(SHARED_EXT)"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/libgpr.$(SHARED_EXT) $(prefix)/lib/libgpr.$(SHARED_EXT)
 ifneq ($(SYSTEM),Darwin)
 	$(Q) ln -sf libgpr.$(SHARED_EXT) $(prefix)/lib/libgpr.so
@@ -1966,10 +1974,12 @@ endif
 endif
 ifeq ($(SYSTEM),MINGW32)
 	$(E) "[INSTALL] Installing grpc.$(SHARED_EXT)"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/grpc.$(SHARED_EXT) $(prefix)/lib/grpc.$(SHARED_EXT)
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/libgrpc-imp.a $(prefix)/lib/libgrpc-imp.a
 else
 	$(E) "[INSTALL] Installing libgrpc.$(SHARED_EXT)"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/libgrpc.$(SHARED_EXT) $(prefix)/lib/libgrpc.$(SHARED_EXT)
 ifneq ($(SYSTEM),Darwin)
 	$(Q) ln -sf libgrpc.$(SHARED_EXT) $(prefix)/lib/libgrpc.so
@@ -1977,10 +1987,12 @@ endif
 endif
 ifeq ($(SYSTEM),MINGW32)
 	$(E) "[INSTALL] Installing grpc_unsecure.$(SHARED_EXT)"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/grpc_unsecure.$(SHARED_EXT) $(prefix)/lib/grpc_unsecure.$(SHARED_EXT)
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/libgrpc_unsecure-imp.a $(prefix)/lib/libgrpc_unsecure-imp.a
 else
 	$(E) "[INSTALL] Installing libgrpc_unsecure.$(SHARED_EXT)"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/libgrpc_unsecure.$(SHARED_EXT) $(prefix)/lib/libgrpc_unsecure.$(SHARED_EXT)
 ifneq ($(SYSTEM),Darwin)
 	$(Q) ln -sf libgrpc_unsecure.$(SHARED_EXT) $(prefix)/lib/libgrpc_unsecure.so
@@ -1996,10 +2008,12 @@ endif
 install-shared_cxx: shared_cxx strip-shared_cxx install-shared_c
 ifeq ($(SYSTEM),MINGW32)
 	$(E) "[INSTALL] Installing grpc++.$(SHARED_EXT)"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/grpc++.$(SHARED_EXT) $(prefix)/lib/grpc++.$(SHARED_EXT)
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/libgrpc++-imp.a $(prefix)/lib/libgrpc++-imp.a
 else
 	$(E) "[INSTALL] Installing libgrpc++.$(SHARED_EXT)"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/libgrpc++.$(SHARED_EXT) $(prefix)/lib/libgrpc++.$(SHARED_EXT)
 ifneq ($(SYSTEM),Darwin)
 	$(Q) ln -sf libgrpc++.$(SHARED_EXT) $(prefix)/lib/libgrpc++.so
@@ -2015,10 +2029,12 @@ endif
 install-shared_csharp: shared_csharp strip-shared_csharp
 ifeq ($(SYSTEM),MINGW32)
 	$(E) "[INSTALL] Installing grpc_csharp_ext.$(SHARED_EXT)"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/grpc_csharp_ext.$(SHARED_EXT) $(prefix)/lib/grpc_csharp_ext.$(SHARED_EXT)
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/libgrpc_csharp_ext-imp.a $(prefix)/lib/libgrpc_csharp_ext-imp.a
 else
 	$(E) "[INSTALL] Installing libgrpc_csharp_ext.$(SHARED_EXT)"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/libgrpc_csharp_ext.$(SHARED_EXT) $(prefix)/lib/libgrpc_csharp_ext.$(SHARED_EXT)
 ifneq ($(SYSTEM),Darwin)
 	$(Q) ln -sf libgrpc_csharp_ext.$(SHARED_EXT) $(prefix)/lib/libgrpc_csharp_ext.so
@@ -2047,8 +2063,11 @@ ifeq ($(SYSTEM),MINGW32)
 	$(Q) false
 else
 	$(E) "[INSTALL] Installing grpc protoc plugins"
+	$(Q) $(INSTALL) -d $(prefix)/bin
 	$(Q) $(INSTALL) $(BINDIR)/$(CONFIG)/grpc_cpp_plugin $(prefix)/bin/grpc_cpp_plugin
+	$(Q) $(INSTALL) -d $(prefix)/bin
 	$(Q) $(INSTALL) $(BINDIR)/$(CONFIG)/grpc_python_plugin $(prefix)/bin/grpc_python_plugin
+	$(Q) $(INSTALL) -d $(prefix)/bin
 	$(Q) $(INSTALL) $(BINDIR)/$(CONFIG)/grpc_ruby_plugin $(prefix)/bin/grpc_ruby_plugin
 endif
 

templates/Makefile.template

@@ -161,7 +161,7 @@ LD = $(LD_$(CONFIG))
 LDXX = $(LDXX_$(CONFIG))
 AR = ar
 STRIP = strip --strip-unneeded
-INSTALL = install -D
+INSTALL = install
 RM = rm -f
 
 ifndef VALID_CONFIG_$(CONFIG)
@@ -728,10 +728,12 @@ install-headers: install-headers_c install-headers_cxx
 
 install-headers_c:
 	$(E) "[INSTALL] Installing public C headers"
+	$(Q) $(foreach h, $(PUBLIC_HEADERS_C), $(INSTALL) -d $(prefix)/$(dir $(h)) && ) exit 0 || exit 1
 	$(Q) $(foreach h, $(PUBLIC_HEADERS_C), $(INSTALL) $(h) $(prefix)/$(h) && ) exit 0 || exit 1
 
 install-headers_cxx:
 	$(E) "[INSTALL] Installing public C++ headers"
+	$(Q) $(foreach h, $(PUBLIC_HEADERS_CXX), $(INSTALL) -d $(prefix)/$(dir $(h)) && ) exit 0 || exit 1
 	$(Q) $(foreach h, $(PUBLIC_HEADERS_CXX), $(INSTALL) $(h) $(prefix)/$(h) && ) exit 0 || exit 1
 
 install-static: install-static_c install-static_cxx
@@ -741,6 +743,7 @@ install-static_c: static_c strip-static_c
 % if lib.language == "c":
 % if lib.build == "all":
 	$(E) "[INSTALL] Installing lib${lib.name}.a"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/lib${lib.name}.a $(prefix)/lib/lib${lib.name}.a
 % endif
 % endif
@@ -751,6 +754,7 @@ install-static_cxx: static_cxx strip-static_cxx
 % if lib.language == "c++":
 % if lib.build == "all":
 	$(E) "[INSTALL] Installing lib${lib.name}.a"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/lib${lib.name}.a $(prefix)/lib/lib${lib.name}.a
 % endif
 % endif
@@ -762,10 +766,12 @@ install-static_cxx: static_cxx strip-static_cxx
 % if lib.build == "all":
 ifeq ($(SYSTEM),MINGW32)
 	$(E) "[INSTALL] Installing ${lib.name}.$(SHARED_EXT)"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/${lib.name}.$(SHARED_EXT) $(prefix)/lib/${lib.name}.$(SHARED_EXT)
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/lib${lib.name}-imp.a $(prefix)/lib/lib${lib.name}-imp.a
 else
 	$(E) "[INSTALL] Installing lib${lib.name}.$(SHARED_EXT)"
+	$(Q) $(INSTALL) -d $(prefix)/lib
 	$(Q) $(INSTALL) $(LIBDIR)/$(CONFIG)/lib${lib.name}.$(SHARED_EXT) $(prefix)/lib/lib${lib.name}.$(SHARED_EXT)
 ifneq ($(SYSTEM),Darwin)
 	$(Q) ln -sf lib${lib.name}.$(SHARED_EXT) $(prefix)/lib/lib${lib.name}.so
@@ -808,6 +814,7 @@ else
 	$(E) "[INSTALL] Installing grpc protoc plugins"
 % for tgt in targets:
 % if tgt.build == 'protoc':
+	$(Q) $(INSTALL) -d $(prefix)/bin
 	$(Q) $(INSTALL) $(BINDIR)/$(CONFIG)/${tgt.name} $(prefix)/bin/${tgt.name}
 % endif
 % endfor