diff --git a/depends/Makefile b/depends/Makefile
index 1ad21f6821..ddf5b61734 100644
--- a/depends/Makefile
+++ b/depends/Makefile
@@ -164,11 +164,7 @@ $(host_arch)_$(host_os)_native_toolchain?=$($(host_os)_native_toolchain)
 include funcs.mk
 
 binutils_path=$($($(host_arch)_$(host_os)_native_binutils)_prefixbin)
-ifeq ($(strip $(FORCE_USE_SYSTEM_CLANG)),)
-toolchain_path=$($($(host_arch)_$(host_os)_native_toolchain)_prefixbin)
-else
-toolchain_path=
-endif
+
 final_build_id_long+=$(shell $(build_SHA256SUM) config.site.in)
 final_build_id+=$(shell echo -n "$(final_build_id_long)" | $(build_SHA256SUM) | cut -c-$(HASH_LENGTH))
 $(host_prefix)/.stamp_$(final_build_id): $(native_packages) $(packages)
@@ -179,11 +175,35 @@ $(host_prefix)/.stamp_$(final_build_id): $(native_packages) $(packages)
 	$(AT)cd $(@D); $(foreach package,$^, tar xf $($(package)_cached); )
 	$(AT)touch $@
 
+# $PATH is not preserved between ./configure and make by convention. Its
+# modification and overriding at ./configure time is (as I understand it)
+# supposed to be captured by the AC_{PROG_{,OBJ}CXX,PATH_{PROG,TOOL}} macros,
+# which will expand the program names to their full absolute paths. The notable
+# exception is command line overriding: ./configure CC=clang, which skips the
+# program name expansion step, and works because the user implicitly indicates
+# with CC=clang that clang will be available in $PATH at all times, and is most
+# likely part of the user's system.
+#
+# Therefore, when we "seed the autoconf cache"/"override well-known program
+# vars" by setting AR=<blah> in our config.site, either one of two things needs
+# to be true for the build system to work correctly:
+#
+#   1. If we refer to the program by name (e.g. AR=riscv64-gnu-linux-ar), the
+#      tool needs to be available in $PATH at all times.
+#
+#   2. If the tool is _**not**_ expected to be available in $PATH at all times
+#      (such as is the case for our native_cctools binutils tools), it needs to
+#      be referred to by its absolute path, such as would be output by the
+#      AC_PATH_{PROG,TOOL} macros.
+#
+# Minor note: it is also okay to refer to tools by their absolute path even if
+# we expect them to be available in $PATH at all times, more specificity does
+# not hurt.
 $(host_prefix)/share/config.site : config.site.in $(host_prefix)/.stamp_$(final_build_id)
 	$(AT)@mkdir -p $(@D)
 	$(AT)sed -e 's|@HOST@|$(host)|' \
-            -e 's|@CC@|$(toolchain_path)$(host_CC)|' \
-            -e 's|@CXX@|$(toolchain_path)$(host_CXX)|' \
+            -e 's|@CC@|$(host_CC)|' \
+            -e 's|@CXX@|$(host_CXX)|' \
             -e 's|@AR@|$(binutils_path)$(host_AR)|' \
             -e 's|@RANLIB@|$(binutils_path)$(host_RANLIB)|' \
             -e 's|@NM@|$(binutils_path)$(host_NM)|' \
diff --git a/depends/hosts/darwin.mk b/depends/hosts/darwin.mk
index 4a70d55405..fb947bf337 100644
--- a/depends/hosts/darwin.mk
+++ b/depends/hosts/darwin.mk
@@ -7,8 +7,33 @@ LD64_VERSION=530
 OSX_SDK=$(SDK_PATH)/Xcode-$(XCODE_VERSION)-$(XCODE_BUILD_ID)-extracted-SDK-with-libcxx-headers
 
 ifeq ($(strip $(FORCE_USE_SYSTEM_CLANG)),)
+# FORCE_USE_SYSTEM_CLANG is empty, so we use our depends-managed, pinned clang
+# from llvm.org
+
+# The native_cctools package is what provides clang when FORCE_USE_SYSTEM_CLANG
+# is empty
+darwin_native_toolchain=native_cctools
+
+clang_prog=$(build_prefix)/bin/clang
+clangxx_prog=$(clang_prog)++
+
 clang_resource_dir=$(build_prefix)/lib/clang/$(native_cctools_clang_version)
 else
+# FORCE_USE_SYSTEM_CLANG is non-empty, so we use the clang from the user's
+# system
+
+darwin_native_toolchain=
+
+# We can't just use $(shell command -v clang) because GNU Make handles builtins
+# in a special way and doesn't know that `command` is a POSIX-standard builtin
+# prior to 1af314465e5dfe3e8baa839a32a72e83c04f26ef, first released in v4.2.90.
+# At the time of writing, GNU Make v4.2.1 is still being used in supported
+# distro releases.
+#
+# Source: https://lists.gnu.org/archive/html/bug-make/2017-11/msg00017.html
+clang_prog=$(shell $(SHELL) $(.SHELLFLAGS) "command -v clang")
+clangxx_prog=$(shell $(SHELL) $(.SHELLFLAGS) "command -v clang++")
+
 clang_resource_dir=$(shell clang -print-resource-dir)
 endif
 
@@ -62,7 +87,7 @@ endif
 darwin_CC=env -u C_INCLUDE_PATH -u CPLUS_INCLUDE_PATH \
               -u OBJC_INCLUDE_PATH -u OBJCPLUS_INCLUDE_PATH -u CPATH \
               -u LIBRARY_PATH \
-            clang --target=$(host) -mmacosx-version-min=$(OSX_MIN_VERSION) \
+            $(clang_prog) --target=$(host) -mmacosx-version-min=$(OSX_MIN_VERSION) \
               -B$(build_prefix)/bin -mlinker-version=$(LD64_VERSION) \
               --sysroot=$(OSX_SDK) \
               -Xclang -internal-externc-isystem$(clang_resource_dir)/include \
@@ -70,7 +95,7 @@ darwin_CC=env -u C_INCLUDE_PATH -u CPLUS_INCLUDE_PATH \
 darwin_CXX=env -u C_INCLUDE_PATH -u CPLUS_INCLUDE_PATH \
                -u OBJC_INCLUDE_PATH -u OBJCPLUS_INCLUDE_PATH -u CPATH \
                -u LIBRARY_PATH \
-             clang++ --target=$(host) -mmacosx-version-min=$(OSX_MIN_VERSION) \
+             $(clangxx_prog) --target=$(host) -mmacosx-version-min=$(OSX_MIN_VERSION) \
                -B$(build_prefix)/bin -mlinker-version=$(LD64_VERSION) \
                --sysroot=$(OSX_SDK) \
                -stdlib=libc++ -nostdinc++ \
@@ -88,10 +113,4 @@ darwin_debug_CFLAGS=-O1
 darwin_debug_CXXFLAGS=$(darwin_debug_CFLAGS)
 
 darwin_native_binutils=native_cctools
-ifeq ($(strip $(FORCE_USE_SYSTEM_CLANG)),)
-darwin_native_toolchain=native_cctools
-else
-darwin_native_toolchain=
-endif
-
 darwin_cmake_system=Darwin