diff --git a/bin/ruby-build b/bin/ruby-build
index ebc4dcad..1e931da1 100755
--- a/bin/ruby-build
+++ b/bin/ruby-build
@@ -18,7 +18,7 @@
 #   -6, --ipv6      Resolve names to IPv6 addresses only
 #
 
-RUBY_BUILD_VERSION="20260902"
+RUBY_BUILD_VERSION="20260916"
 
 OLDIFS="$IFS"
 
@@ -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/script/release b/script/release
index e1352e4d..b457a40b 100755
--- a/script/release
+++ b/script/release
@@ -8,7 +8,7 @@
 # - creates a new Release on GitHub
 # - [automated] a GitHub Action will create a Homebrew PR for the new release
 
-set -e
+set -ex
 
 git fetch -q --tags origin master
 git checkout -q master
diff --git a/share/man/man1/ruby-build.1 b/share/man/man1/ruby-build.1
index 145e39a2..d81aae40 100644
--- a/share/man/man1/ruby-build.1
+++ b/share/man/man1/ruby-build.1
@@ -2,12 +2,12 @@
 .\"     Title: ruby-build
 .\"    Author: Mislav Marohnić
 .\" Generator: Asciidoctor 2.0.26
-.\"      Date: 2026-05-01
+.\"      Date: 2026-05-07
 .\"    Manual: ruby-build Manual
-.\"    Source: ruby-build 20260902
+.\"    Source: ruby-build 20260916
 .\"  Language: English
 .\"
-.TH "RUBY\-BUILD" "1" "2026-05-01" "ruby\-build 20260902" "ruby\-build Manual"
+.TH "RUBY\-BUILD" "1" "2026-05-07" "ruby\-build 20260916" "ruby\-build Manual"
 .ie \n(.g .ds Aq \(aq
 .el       .ds Aq '
 .ss \n[.ss] 0
diff --git a/share/ruby-build/4.0.7 b/share/ruby-build/4.0.7
new file mode 100644
index 00000000..d8f0affb
--- /dev/null
+++ b/share/ruby-build/4.0.7
@@ -0,0 +1,2 @@
+install_package "openssl-3.0.22" "https://github.com/openssl/openssl/releases/download/openssl-3.0.22/openssl-3.0.22.tar.gz#67ebca7e50d17383028045486653492195b83db95f8558709701bb47b5c1ef81" openssl --if needs_openssl:1.1.1-3.x.x
+install_package "ruby-4.0.7" "https://cache.ruby-lang.org/pub/ruby/4.0/ruby-4.0.7.tar.gz#911ace20f90d068ca0e4dda6d0e4f0f81e52e52f2dd4f4004c721e253412e82d" enable_shared standard
diff --git a/test/compiler.bats b/test/compiler.bats
index 58728379..14ac4daa 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
+}