diff --git a/bin/ruby-build b/bin/ruby-build
index 6b56ec4252..5000794fe7 100755
--- a/bin/ruby-build
+++ b/bin/ruby-build
@@ -754,6 +754,13 @@ build_package_standard() {
       # override them and notably lose the -O3, producing a -O0 Ruby.
       export cflags="-std=gnu17 $cflags"
     fi
+    if [ "$package_var_name" = "RUBY" ] && is_mac && ! is_mac 2700; then
+      # The macOS 27 SDK declares dup3() and pipe2() as available since macOS 27.0.
+      # Ruby's configure detects them even when building for an older macOS, where
+      # they are only weakly linked and are NULL at runtime, which makes miniruby
+      # crash during the build: https://bugs.ruby-lang.org/issues/22311
+      export ac_cv_func_dup3=no ac_cv_func_pipe2=no
+    fi
     # ./configure --prefix=/path/to/ruby
     # shellcheck disable=SC2086,SC2153
     capture_command ${!PACKAGE_CONFIGURE:-./configure} --prefix="${!PACKAGE_PREFIX_PATH:-$PREFIX_PATH}" \
diff --git a/test/compiler.bats b/test/compiler.bats
index 58728379f6..14ac4daa7e 100755
--- a/test/compiler.bats
+++ b/test/compiler.bats
@@ -12,7 +12,7 @@ export -n RUBY_CONFIGURE_OPTS
   cd "$INSTALL_ROOT"
 
   stub_repeated uname '-s : echo Darwin'
-  stub sw_vers '-productVersion : echo 10.10'
+  stub_repeated sw_vers '-productVersion : echo 10.10'
   stub_repeated brew 'false'
   # shellcheck disable=SC2016
   stub_repeated make 'echo "make $(inspect_args "$@")" >> build.log'
@@ -43,3 +43,77 @@ OUT
   unstub brew
   unstub make
 }
+
+@test "dup3 and pipe2 are hidden from configure when building on older macOS" {
+  mkdir -p "$INSTALL_ROOT"
+  cd "$INSTALL_ROOT"
+
+  stub_repeated uname '-s : echo Darwin'
+  stub_repeated sw_vers '-productVersion : echo 26.6.2'
+  stub_repeated brew 'false'
+  # shellcheck disable=SC2016
+  stub_repeated make 'echo "make $(inspect_args "$@")" >> build.log'
+
+  cat > ./configure <<CON
+#!${BASH}
+echo ./configure "\$@" > build.log
+echo dup3=\${ac_cv_func_dup3-unset} >> build.log
+echo pipe2=\${ac_cv_func_pipe2-unset} >> build.log
+CON
+  chmod +x ./configure
+
+  run_inline_definition <<DEF
+build_package_standard ruby-3.4.0
+DEF
+  assert_success
+  run cat build.log
+  assert_output <<OUT
+./configure --prefix=$INSTALL_ROOT --with-ext=openssl,psych,+
+dup3=no
+pipe2=no
+make -j 2
+make install
+OUT
+
+  unstub uname
+  unstub sw_vers
+  unstub brew
+  unstub make
+}
+
+@test "dup3 and pipe2 are left to configure on macOS 27" {
+  mkdir -p "$INSTALL_ROOT"
+  cd "$INSTALL_ROOT"
+
+  stub_repeated uname '-s : echo Darwin'
+  stub_repeated sw_vers '-productVersion : echo 27.0'
+  stub_repeated brew 'false'
+  # shellcheck disable=SC2016
+  stub_repeated make 'echo "make $(inspect_args "$@")" >> build.log'
+
+  cat > ./configure <<CON
+#!${BASH}
+echo ./configure "\$@" > build.log
+echo dup3=\${ac_cv_func_dup3-unset} >> build.log
+echo pipe2=\${ac_cv_func_pipe2-unset} >> build.log
+CON
+  chmod +x ./configure
+
+  run_inline_definition <<DEF
+build_package_standard ruby-3.4.0
+DEF
+  assert_success
+  run cat build.log
+  assert_output <<OUT
+./configure --prefix=$INSTALL_ROOT --with-ext=openssl,psych,+
+dup3=unset
+pipe2=unset
+make -j 2
+make install
+OUT
+
+  unstub uname
+  unstub sw_vers
+  unstub brew
+  unstub make
+}