diff --git a/.gitattributes b/.gitattributes
index 6ac6e6fcc3f579..f98c091e3f0464 100644
--- a/.gitattributes
+++ b/.gitattributes
@@ -7,3 +7,8 @@ tool/update-deps diff=ruby
 tool/make-snapshot diff=ruby
 tool/format-release diff=ruby
 tool/leaked-globals diff=ruby
+
+# To strip CR from the batch files, set the `diff.dos.textconv` filter
+# like as `git config diff.dos.textconv $'sed \'s/\r$//\''`.
+*.bat diff=dos
+*.cmd diff=dos
diff --git a/NEWS.md b/NEWS.md
index 38ca8667a87ecb..9a1dd9c9337587 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -62,6 +62,7 @@ releases.
 * debug 1.11.1
 * mutex_m 0.3.0
 * resolv-replace 0.2.0
+* syslog 0.4.0
 * rdoc 7.1.0
 
 ### RubyGems and Bundler
diff --git a/configure.ac b/configure.ac
index 4e7367804d3d6b..2d9ccf1442920e 100644
--- a/configure.ac
+++ b/configure.ac
@@ -743,6 +743,12 @@ AS_CASE(["$GCC:${warnflags+set}:${extra_warnflags:+set}:"],
     AS_CASE([ $CFLAGS ], [*" -save-temps="*|*" -save-temps "*], [], [
 	extra_warnflags="$extra_warnflags -Werror=misleading-indentation"
     ])
+    AS_CASE([$target_os], [mingw*], [
+	# 64bit Windows is IL32P64; shorten-64-to-32 causes tons of warnigs
+	extra_warnflags="$extra_warnflags -Wno-shorten-64-to-32"
+    ], [
+	extra_warnflags="$extra_warnflags -Werror=shorten-64-to-32"
+    ])
 
     # ICC doesn't support -Werror=
     AS_IF([test $icc_version -gt 0], [
@@ -756,7 +762,6 @@ AS_CASE(["$GCC:${warnflags+set}:${extra_warnflags:+set}:"],
 		 -Werror=implicit-function-declaration \
 		 -Werror=implicit-int \
 		 -Werror=pointer-arith \
-		 -Werror=shorten-64-to-32 \
 		 -Werror=write-strings \
 		 -Werror=old-style-definition \
 		 -Wimplicit-fallthrough=0 \
diff --git a/gems/bundled_gems b/gems/bundled_gems
index 98a6ca2cea8ea2..e85061bc0f842e 100644
--- a/gems/bundled_gems
+++ b/gems/bundled_gems
@@ -32,7 +32,7 @@ resolv-replace      0.2.0   https://github.com/ruby/resolv-replace
 rinda               0.2.0   https://github.com/ruby/rinda
 drb                 2.2.3   https://github.com/ruby/drb
 nkf                 0.2.0   https://github.com/ruby/nkf
-syslog              0.3.0   https://github.com/ruby/syslog
+syslog              0.4.0   https://github.com/ruby/syslog
 csv                 3.3.5   https://github.com/ruby/csv
 repl_type_completor 0.1.12  https://github.com/ruby/repl_type_completor   26b8e964557690c0b539cff8940bcfb1591f1fe6
 ostruct             0.6.3   https://github.com/ruby/ostruct
diff --git a/include/ruby/internal/fl_type.h b/include/ruby/internal/fl_type.h
index 2afb3f1fa348f2..e3878d9ed7d567 100644
--- a/include/ruby/internal/fl_type.h
+++ b/include/ruby/internal/fl_type.h
@@ -108,8 +108,6 @@
 #define RB_OBJ_FREEZE_RAW    RB_OBJ_FREEZE_RAW
 #define RB_OBJ_FROZEN        RB_OBJ_FROZEN
 #define RB_OBJ_FROZEN_RAW    RB_OBJ_FROZEN_RAW
-#define RB_OBJ_UNTRUST       RB_OBJ_TAINT
-#define RB_OBJ_UNTRUSTED     RB_OBJ_TAINTED
 /** @endcond */
 
 /**
@@ -134,15 +132,6 @@
 #define OBJ_FREEZE_RAW  RB_OBJ_FREEZE_RAW  /**< @old{RB_OBJ_FREEZE_RAW} */
 #define OBJ_FROZEN      RB_OBJ_FROZEN      /**< @old{RB_OBJ_FROZEN} */
 #define OBJ_FROZEN_RAW  RB_OBJ_FROZEN_RAW  /**< @old{RB_OBJ_FROZEN_RAW} */
-#define OBJ_INFECT      RB_OBJ_INFECT      /**< @old{RB_OBJ_INFECT} */
-#define OBJ_INFECT_RAW  RB_OBJ_INFECT_RAW  /**< @old{RB_OBJ_INFECT_RAW} */
-#define OBJ_TAINT       RB_OBJ_TAINT       /**< @old{RB_OBJ_TAINT} */
-#define OBJ_TAINTABLE   RB_OBJ_TAINTABLE   /**< @old{RB_OBJ_TAINT_RAW} */
-#define OBJ_TAINTED     RB_OBJ_TAINTED     /**< @old{RB_OBJ_TAINTED} */
-#define OBJ_TAINTED_RAW RB_OBJ_TAINTED_RAW /**< @old{RB_OBJ_TAINTED_RAW} */
-#define OBJ_TAINT_RAW   RB_OBJ_TAINT_RAW   /**< @old{RB_OBJ_TAINT_RAW} */
-#define OBJ_UNTRUST     RB_OBJ_UNTRUST     /**< @old{RB_OBJ_TAINT} */
-#define OBJ_UNTRUSTED   RB_OBJ_UNTRUSTED   /**< @old{RB_OBJ_TAINTED} */
 /** @} */
 
 /**
diff --git a/spec/ruby/core/io/buffer/map_spec.rb b/spec/ruby/core/io/buffer/map_spec.rb
index d980eb0ae0451a..d60036307f8774 100644
--- a/spec/ruby/core/io/buffer/map_spec.rb
+++ b/spec/ruby/core/io/buffer/map_spec.rb
@@ -2,21 +2,33 @@
 
 describe "IO::Buffer.map" do
   before :all do
-    @big_file_name = tmp("big_file")
-    # Usually 4 kibibytes + 16 bytes
-    File.write(@big_file_name, "12345678" * (IO::Buffer::PAGE_SIZE / 8 + 2))
+    @tmp_files = []
+
+    @big_file_name = nil
+    @small_file_name = nil
   end
 
   after :all do
-    File.delete(@big_file_name)
+    @tmp_files.each {|file| File.delete(file)}
   end
 
   def open_fixture
-    File.open("#{__dir__}/../fixtures/read_text.txt", "r+")
+    unless @small_file_name
+      @small_file_name = tmp("read_text.txt")
+      File.copy_stream(fixture(__dir__, "read_text.txt"), @small_file_name)
+      @tmp_files << @small_file_name
+    end
+    File.open(@small_file_name, "rb+")
   end
 
   def open_big_file_fixture
-    File.open(@big_file_name, "r+")
+    unless @big_file_name
+      @big_file_name = tmp("big_file")
+      # Usually 4 kibibytes + 16 bytes
+      File.write(@big_file_name, "12345678" * (IO::Buffer::PAGE_SIZE / 8 + 2))
+      @tmp_files << @big_file_name
+    end
+    File.open(@big_file_name, "rb+")
   end
 
   after :each do
@@ -89,24 +101,19 @@ def open_big_file_fixture
   end
 
   context "with an empty file" do
-    ruby_version_is ""..."4.0" do
-      it "raises a SystemCallError" do
-        @file = File.open("#{__dir__}/../fixtures/empty.txt", "r+")
-        -> { IO::Buffer.map(@file) }.should raise_error(SystemCallError)
-      end
-    end
-
     ruby_version_is "4.0" do
       it "raises ArgumentError" do
-        @file = File.open("#{__dir__}/../fixtures/empty.txt", "r+")
+        file_name = tmp("empty.txt")
+        @file = File.open(file_name, "wb+")
+        @tmp_files << file_name
         -> { IO::Buffer.map(@file) }.should raise_error(ArgumentError, "Invalid negative or zero file size!")
       end
     end
   end
 
   context "with a file opened only for reading" do
-    it "raises a SystemCallError if no flags are used" do
-      @file = File.open("#{__dir__}/../fixtures/read_text.txt", "r")
+    it "raises a SystemCallError unless read-only" do
+      @file = File.open(fixture(__dir__, "read_text.txt"), "rb")
       -> { IO::Buffer.map(@file) }.should raise_error(SystemCallError)
     end
   end
@@ -128,15 +135,6 @@ def open_big_file_fixture
     end
 
     context "if size is 0" do
-      ruby_version_is ""..."4.0" do
-        platform_is_not :windows do
-          it "raises a SystemCallError" do
-            @file = open_fixture
-            -> { IO::Buffer.map(@file, 0) }.should raise_error(SystemCallError)
-          end
-        end
-      end
-
       ruby_version_is "4.0" do
         it "raises ArgumentError" do
           @file = open_fixture
@@ -247,18 +245,6 @@ def open_big_file_fixture
       -> { IO::Buffer.map(@file, 4, nil) }.should raise_error(TypeError, /no implicit conversion/)
     end
 
-    it "raises a SystemCallError if offset is not an allowed value" do
-      @file = open_fixture
-      -> { IO::Buffer.map(@file, 4, 3) }.should raise_error(SystemCallError)
-    end
-
-    ruby_version_is ""..."4.0" do
-      it "raises a SystemCallError if offset is negative" do
-        @file = open_fixture
-        -> { IO::Buffer.map(@file, 4, -1) }.should raise_error(SystemCallError)
-      end
-    end
-
     ruby_version_is "4.0" do
       it "raises ArgumentError if offset is negative" do
         @file = open_fixture
@@ -279,7 +265,7 @@ def open_big_file_fixture
       end
 
       it "allows mapping read-only files" do
-        @file = File.open("#{__dir__}/../fixtures/read_text.txt", "r")
+        @file = File.open(fixture(__dir__, "read_text.txt"), "rb")
         @buffer = IO::Buffer.map(@file, nil, 0, IO::Buffer::READONLY)
 
         @buffer.should.readonly?
@@ -308,11 +294,11 @@ def open_big_file_fixture
         @buffer.set_string("test12345")
         @buffer.get_string.should == "test12345".b
 
-        @file.read.should == "abcâdef\n"
+        @file.read.should == "abcâdef\n".b
       end
 
       it "allows mapping read-only files and modifying the buffer" do
-        @file = File.open("#{__dir__}/../fixtures/read_text.txt", "r")
+        @file = File.open(fixture(__dir__, "read_text.txt"), "rb")
         @buffer = IO::Buffer.map(@file, nil, 0, IO::Buffer::PRIVATE)
 
         @buffer.should.private?
@@ -323,7 +309,7 @@ def open_big_file_fixture
         @buffer.set_string("test12345")
         @buffer.get_string.should == "test12345".b
 
-        @file.read.should == "abcâdef\n"
+        @file.read.should == "abcâdef\n".b
       end
 
       platform_is_not :windows do
diff --git a/spec/ruby/core/io/buffer/shared_spec.rb b/spec/ruby/core/io/buffer/shared_spec.rb
index 4f3bce5448fee0..be8c29471af880 100644
--- a/spec/ruby/core/io/buffer/shared_spec.rb
+++ b/spec/ruby/core/io/buffer/shared_spec.rb
@@ -12,10 +12,15 @@
   end
 
   it "is true for a non-private buffer created with .map" do
-    file = File.open("#{__dir__}/../fixtures/read_text.txt", "r+")
+    path = tmp("read_text.txt")
+    File.copy_stream(fixture(__dir__, "read_text.txt"), path)
+    file = File.open(path, "r+")
     @buffer = IO::Buffer.map(file)
-    file.close
     @buffer.shared?.should be_true
+  ensure
+    @buffer.free
+    file.close
+    File.unlink(path)
   end
 
   it "is false for an unshared buffer" do
diff --git a/win32/configure.bat b/win32/configure.bat
index 9355caa4d852da..d4e010ac4b0374 100755
--- a/win32/configure.bat
+++ b/win32/configure.bat
@@ -1,7 +1,6 @@
 @echo off
 @setlocal EnableExtensions DisableDelayedExpansion || exit /b -1
 set PROMPT=$E[94m+$E[m$S
-set witharg=
 
 if "%~dp0" == "%CD%\" (
     echo don't run in win32 directory.
@@ -19,180 +18,141 @@ call set "WIN32DIR=%%WIN32DIR:%~x0:/:=:/:%%"
 call set "WIN32DIR=%%WIN32DIR:/%~n0:/:=:/:%%"
 set "WIN32DIR=%WIN32DIR:~0,-3%"
 
-set XINCFLAGS=
-set XLDFLAGS=
+set configure=%~0
+set optdirs=
 set pathlist=
 set config_make=confargs~%RANDOM%.mak
-set confargs=%config_make:.mak=.c%
+set confargs=%config_make:.mak=.sub%
+set debug_configure=
 echo>%config_make% # CONFIGURE
-(
-  echo #define $ $$ //
-  echo !ifndef CONFIGURE_ARGS
-  echo #define CONFIGURE_ARGS \
-) >%confargs%
+type nul > %confargs%
 :loop
-set opt=%1
-if "%1" == "" goto :end
-if "%1" == "--debug-configure" (echo on & shift & goto :loop)
-if "%1" == "--no-debug-configure" (echo off & shift & goto :loop)
-if "%1" == "--prefix" goto :prefix
-if "%1" == "--srcdir" goto :srcdir
-if "%1" == "srcdir" goto :srcdir
-if "%1" == "--target" goto :target
-if "%1" == "target" goto :target
-if "%1" == "--with-static-linked-ext" goto :extstatic
-if "%1" == "--program-prefix" goto :pprefix
-if "%1" == "--program-suffix" goto :suffix
-if "%1" == "--program-transform-name" goto :transform_name
-if "%1" == "--program-name" goto :installname
-if "%1" == "--install-name" goto :installname
-if "%1" == "--so-name" goto :soname
-if "%1" == "--enable-install-doc" goto :enable-rdoc
-if "%1" == "--disable-install-doc" goto :disable-rdoc
-if "%1" == "--enable-install-static-library" goto :enable-lib
-if "%1" == "--disable-install-static-library" goto :disable-lib
-if "%1" == "--enable-debug-env" goto :enable-debug-env
-if "%1" == "--disable-debug-env" goto :disable-debug-env
-if "%1" == "--enable-devel" goto :enable-devel
-if "%1" == "--disable-devel" goto :disable-devel
-if "%1" == "--enable-rubygems" goto :enable-rubygems
-if "%1" == "--disable-rubygems" goto :disable-rubygems
-if "%1" == "--extout" goto :extout
-if "%1" == "--path" goto :path
-if "%1" == "--with-baseruby" goto :baseruby
-if "%1" == "--without-baseruby" goto :nobaseruby
-if "%1" == "--with-ntver" goto :ntver
-if "%1" == "--with-libdir" goto :libdir
-if "%1" == "--with-git" goto :git
-if "%1" == "--without-git" goto :nogit
-if "%1" == "--without-ext" goto :witharg
-if "%1" == "--without-extensions" goto :witharg
-if "%1" == "--with-opt-dir" goto :opt-dir
-if "%1" == "--with-gmp" goto :gmp
-if "%1" == "--with-gmp-dir" goto :gmp-dir
-if "%opt:~0,10%" == "--without-" goto :withoutarg
-if "%opt:~0,7%" == "--with-" goto :witharg
-if "%1" == "-h" goto :help
-if "%1" == "--help" goto :help
+if [%1] == [] goto :end ;
+if "%~1" == "" (shift & goto :loop)
+for /f "delims== tokens=1,*" %%I in ("%~1") do ((set "opt=%%I") && (set "arg=%%J"))
+  set "eq=="
+  if "%arg%" == "" if not "%~1" == "%opt%=%arg%" (set "eq=")
+  shift
+  if "%opt%" == "--debug-configure" (
+    echo on
+    set "debug_configure=yes"
+    goto :loop ;
+  )
+  if "%opt%" == "--no-debug-configure" (
+    echo off
+    set "debug_configure="
+    goto :loop ;
+  )
+  if "%opt%" == "--prefix" goto :dir
+  if "%opt%" == "srcdir" set "opt=--srcdir"
+  if "%opt%" == "--srcdir" goto :dir
+  if "%opt%" == "--target" goto :target
+  if "%opt%" == "target" goto :target
+  if "%opt:~0,10%" == "--program-" goto :program_name
+  if "%opt%" == "--install-name" (set "var=RUBY_INSTALL_NAME" & goto :name)
+  if "%opt%" == "--so-name" (set "var=RUBY_SO_NAME" & goto :name)
+  if "%opt%" == "--extout" goto :extout
+  if "%opt%" == "--path" goto :path
+  if "%opt:~0,9%" == "--enable-" (set "enable=yes" & goto :enable)
+  if "%opt:~0,10%" == "--disable-" (set "enable=no" & goto :enable)
+  if "%opt:~0,10%" == "--without-" goto :withoutarg
+  if "%opt:~0,7%" == "--with-" goto :witharg
+  if "%opt%" == "-h" goto :help
+  if "%opt%" == "--help" goto :help
   if "%opt:~0,1%" == "-" (
-    echo>>%confargs%  %1 \
-    set witharg=
-  ) else if "%witharg%" == "" (
-    echo>>%confargs%  %1 \
+    goto :unknown_opt
+  )
+  if "%eq%" == "=" (
+    set "var=%opt%"
+    goto :name
+  )
+  set "arg=%opt%"
+  set "eq=="
+  set "opt=--target"
+  set "target=%arg%"
+:loopend
+  if not "%arg%" == "" (
+    echo>>%confargs%  "%opt%=%arg:$=$$%" \
   ) else (
-    echo>>%confargs% ,%1\
+    echo>>%confargs%  "%opt%%eq%" \
   )
-  shift
-goto :loop ;
-:srcdir
-  echo>> %config_make% srcdir = %~2
-  echo>>%confargs% --srcdir=%2 \
-  shift
-  shift
-goto :loop ;
-:prefix
-  echo>> %config_make% prefix = %~2
-  echo>>%confargs%  %1=%2 \
-  shift
-  shift
-goto :loop ;
-:pprefix
-  echo>> %config_make% PROGRAM_PREFIX = %~2
-  echo>>%confargs%  %1=%2 \
-  shift
-  shift
-goto :loop ;
-:suffix
-  echo>> %config_make% PROGRAM_SUFFIX = %~2
-  echo>>%confargs%  %1=%2 \
-  shift
-  shift
-goto :loop ;
-:installname
-  echo>> %config_make% RUBY_INSTALL_NAME = %~2
-  echo>>%confargs%  %1=%2 \
-  shift
-  shift
-goto :loop ;
-:soname
-  echo>> %config_make% RUBY_SO_NAME = %~2
-  echo>>%confargs%  %1=%2 \
-  shift
-  shift
-goto :loop ;
-:transform_name
-
-  shift
-  shift
 goto :loop ;
 :target
-  echo>> %config_make% target = %~2
-  echo>>%confargs% --target=%2 \
-  if "%~2" == "x64-mswin64" (
-    echo>> %config_make% TARGET_OS = mswin64
+  if "%eq%" == "" (set "arg=%~1" & shift)
+  if "%arg%" == "" (
+    echo 1>&2 %configure%: missing argument for %opt%
+    exit /b 1
   )
-  shift
-  shift
-goto :loop ;
-:extstatic
-  echo>> %config_make% EXTSTATIC = static
-  echo>>%confargs%  %1 \
-  shift
-goto :loop ;
-:enable-rdoc
-  echo>> %config_make% RDOCTARGET = rdoc
-  echo>>%confargs%  %1 \
-  shift
-goto :loop ;
-:disable-rdoc
-  echo>> %config_make% RDOCTARGET = nodoc
-  echo>>%confargs%  %1 \
-  shift
-goto :loop ;
-:enable-lib
-  echo>> %config_make% INSTALL_STATIC_LIBRARY = yes
-  echo>>%confargs%  %1 \
-  shift
-goto :loop ;
-:disable-lib
-  echo>> %config_make% INSTALL_STATIC_LIBRARY = no
-  echo>>%confargs%  %1 \
-  shift
-goto :loop ;
-:enable-debug-env
-  echo>> %config_make% ENABLE_DEBUG_ENV = yes
-  echo>>%confargs%  %1 \
-  shift
-goto :loop ;
-:disable-debug-env
-  echo>> %config_make% ENABLE_DEBUG_ENV = no
-  echo>>%confargs%  %1 \
-  shift
+  set "target=%arg%"
+  set "opt=--target"
+  echo>>%confargs%  "--target=%arg:$=$$%" \
 goto :loop ;
-:enable-devel
-  echo>> %config_make% RUBY_DEVEL = yes
-  echo>>%confargs%  %1 \
-  shift
-goto :loop ;
-:disable-devel
-  echo>> %config_make% RUBY_DEVEL = no
-  echo>>%confargs%  %1 \
-  shift
+:program_name
+  if "%eq%" == "" (set "arg=%~1" & shift)
+  for /f "delims=- tokens=1,*" %I in ("%opt%") do set "var=%%J"
+  if "%var%" == "prefix" (set "var=PROGRAM_PREFIX" & goto :name)
+  if "%var%" == "suffix" (set "var=PROGRAM_SUFFIX" & goto :name)
+  if "%var%" == "name" (set "var=RUBY_INSTALL_NAME" & goto :name)
+  if "%var%" == "transform-name" (
+    echo.1>&2 %configure%: --program-transform-name option is not supported
+    exit /b 1
+  )
+goto :unknown_opt
+:name
+  if "%eq%" == "" (set "arg=%~1" & shift)
+  echo>> %config_make% %var% = %arg%
+goto :loopend ;
+:dir
+  if "%eq%" == "" (set "arg=%~1" & shift)
+  echo>> %config_make% %opt:~2% = %arg:\=/%
+goto :loopend ;
+:enable
+  echo>>%confargs%  "%opt%" \
+  if %enable% == yes (set "opt=%opt:~9%") else (set "opt=%opt:~10%")
+  if "%opt%" == "rdoc" (
+    echo>> %config_make% RDOCTARGET = %enable:yes=r%doc
+  )
+  if "%opt%" == "install-static-library" (
+    echo>> %config_make% INSTALL_STATIC_LIBRARY = %enable%
+  )
+  if "%opt%" == "debug-env" (
+    echo>> %config_make% ENABLE_DEBUG_ENV = %enable%
+  )
+  if "%opt%" == "devel" (
+    echo>> %config_make% RUBY_DEVEL = %enable%
+  )
+  if "%opt%" == "rubygems" (
+    echo>> %config_make% USE_RUBYGEMS = %enable%
+  )
 goto :loop ;
-:enable-rubygems
-  echo>> %config_make% USE_RUBYGEMS = yes
-  echo>>%confargs%  %1 \
-  shift
+:withoutarg
+  echo>>%confargs%  "%opt%" \
+  if "%opt%" == "--without-baseruby" goto :nobaseruby
+  if "%opt%" == "--without-git" goto :nogit
+  if "%opt%" == "--without-ext" goto :witharg
+  if "%opt%" == "--without-extensions" goto :witharg
 goto :loop ;
-:disable-rubygems
-  echo>> %config_make% USE_RUBYGEMS = no
-  echo>>%confargs%  %1 \
-  shift
+:witharg
+  if "%opt%" == "--with-static-linked-ext" goto :extstatic
+  if "%eq%" == "" (set "arg=%~1" & shift)
+  if not "%arg%" == "" (
+    echo>>%confargs%  "%opt%=%arg:$=$$%" \
+  ) else (
+    echo>>%confargs%  "%opt%%eq%" \
+  )
+  if "%opt%" == "--with-baseruby" goto :baseruby
+  if "%opt%" == "--with-ntver" goto :ntver
+  if "%opt%" == "--with-libdir" goto :libdir
+  if "%opt%" == "--with-git" goto :git
+  if "%opt%" == "--with-opt-dir" goto :opt-dir
+  if "%opt%" == "--with-gmp-dir" goto :opt-dir
+  if "%opt%" == "--with-gmp" goto :gmp
+  if "%opt%" == "--with-destdir" goto :destdir
 goto :loop ;
 :ntver
   ::- For version constants, see
   ::- https://learn.microsoft.com/en-us/cpp/porting/modifying-winver-and-win32-winnt#remarks
-  set NTVER=%~2
+  if "%eq%" == "" (set "NTVER=%~1" & shift) else (set "NTVER=%arg%")
   if /i not "%NTVER:~0,2%" == "0x" if /i not "%NTVER:~0,13%" == "_WIN32_WINNT_" (
     for %%i in (A B C D E F G H I J K L M N O P Q R S T U V W X Y Z) do (
       call set NTVER=%%NTVER:%%i=%%i%%
@@ -200,83 +160,60 @@ goto :loop ;
     call set NTVER=_WIN32_WINNT_%%NTVER%%
   )
   echo>> %config_make% NTVER = %NTVER%
-  echo>>%confargs%  %1=%2 \
-  shift
-  shift
-goto :loop ;
+goto :loopend ;
 :extout
-  if not "%~2" == ".ext" (echo>> %config_make% EXTOUT = %~2)
-  echo>>%confargs%  %1=%2 \
-  shift
-  shift
-goto :loop ;
+  if "%eq%" == "" (set "arg=%~1" & shift)
+  if not "%arg%" == ".ext" (echo>> %config_make% EXTOUT = %arg%)
+goto :loopend ;
 :path
-  set pathlist=%pathlist%%~2;
-  echo>>%confargs%  %1=%2 \
-  shift
-  shift
-goto :loop ;
+  if "%eq%" == "" (set "arg=%~1" & shift)
+  set "pathlist=%pathlist%%arg:\=/%;"
+goto :loopend ;
+:extstatic
+  if "%eq%" == "" (set "arg=static" & shift)
+  echo>> %config_make% EXTSTATIC = %arg%
+goto :loopend ;
 :baseruby
   echo>> %config_make% HAVE_BASERUBY = yes
-  echo>> %config_make% BASERUBY = %~2
-  echo>>%confargs%  %1=%2 \
-  shift
-  shift
+  echo>> %config_make% BASERUBY = %arg%
 goto :loop ;
 :nobaseruby
   echo>> %config_make% HAVE_BASERUBY = no
   echo>> %config_make% BASERUBY =
-  echo>>%confargs%  %1 \
-  shift
 goto :loop ;
 :libdir
-  echo>> %config_make% libdir_basename = %~2
-  echo>>%confargs%  %1=%2 \
-  shift
-  shift
+  echo>> %config_make% libdir_basename = %arg%
 goto :loop ;
 :git
-  echo>> %config_make% GIT = %~2
-  echo>>%confargs%  %1=%2 \
-  shift
-  shift
+  echo>> %config_make% GIT = %arg%
 goto :loop ;
 :nogit
   echo>> %config_make% GIT = never-use
   echo>> %config_make% HAVE_GIT = no
-  echo>>%confargs%  %1 \
-  shift
 goto :loop ;
 :gmp
   echo>> %config_make% WITH_GMP = yes
-  echo>>%confargs%  %1 \
-  shift
 goto :loop ;
-:gmp-dir
+:destdir
+  echo>> %config_make% DESTDIR = %arg%
+goto :loop ;
 :opt-dir
-  set opt=%~2
-  for %%I in (%opt:;= %) do (
-    set d=%%I
-    call pushd %%d:/=\%% && (
-      call set XINCFLAGS=%%XINCFLAGS%% -I%%CD:\=/%%/include
-      call set XLDFLAGS=%%XLDFLAGS%% -libpath:%%CD:\=/%%/lib
+  if "%arg%" == "" (
+    echo 1>&2 %configure%: missing argument for %opt%
+    exit /b 1
+  )
+  :optdir-loop
+  for /f "delims=; tokens=1,*" %%I in ("%arg%") do (set "d=%%I" & set "arg=%%J")
+    pushd %d:/=\% && (
+      set "optdirs=%optdirs%;%CD:\=/%"
       popd
     )
-  )
-:witharg
-  echo>>%confargs%  %1=%2\
-  set witharg=1
-  shift
-  shift
-goto :loop ;
-:withoutarg
-  echo>>%confargs%  %1 \
-  shift
+  if not "%arg%" == "" goto :optdir-loop
 goto :loop ;
 :help
   echo Configuration:
   echo   --help                  display this help
-  echo   --srcdir=DIR            find the sources in DIR [configure dir or `..']
+  echo   --srcdir=DIR            find the sources in DIR [configure dir or '..']
   echo Installation directories:
   echo   --prefix=PREFIX         install files in PREFIX [/usr]
   echo System types:
@@ -286,36 +223,50 @@ goto :loop ;
   echo   --with-static-linked-ext link external modules statically
   echo   --with-ext="a,b,..."    use extensions a, b, ...
   echo   --without-ext="a,b,..." ignore extensions a, b, ...
-  echo   --with-opt-dir="DIR-LIST" add optional headers and libraries directories separated by `;'
+  echo   --with-opt-dir="DIR-LIST" add optional headers and libraries directories separated by ';'
   echo   --disable-install-doc   do not install rdoc indexes during install
   echo   --with-ntver=0xXXXX     target NT version (shouldn't use with old SDK)
   echo   --with-ntver=_WIN32_WINNT_XXXX
   echo   --with-ntver=XXXX       same as --with-ntver=_WIN32_WINNT_XXXX
-  echo Note that `,' and `;' need to be enclosed within double quotes in batch file command line.
+  echo Note that '=,;' need to be enclosed within double quotes in batch file command line.
   del %confargs% %config_make%
-goto :exit
+goto :EOF
+:unknown_opt
+  (
+    echo %configure%: unknown option %opt%
+    echo Try --help option.
+  ) 1>&2
+  exit /b 1
 :end
+if "%debug_configure%" == "yes" (type %confargs%)
+if not "%optdirs%" == "" (echo>>%config_make% optdirs = %optdirs:~1%)
 (
-  echo //
-  echo configure_args = CONFIGURE_ARGS
-  echo !endif
-  echo #undef $
-) >> %confargs%
-(
-  cl -EP %confargs% 2>nul | findstr "! ="
   echo.
-  if NOT "%XINCFLAGS%" == "" echo XINCFLAGS = %XINCFLAGS%
-  if NOT "%XLDFLAGS%" == "" echo XLDFLAGS = %XLDFLAGS%
-  if NOT "%pathlist%" == "" (
+  echo configure_args = \
+  type %confargs%
+  echo # configure_args
+
+  echo.
+  echo !if "$(optdirs)" != ""
+  for %%I in ("$(optdirs:\=/)" "$(optdirs:/;=;)") do @echo optdirs = %%~I
+  echo XINCFLAGS = -I"$(optdirs:;=/include" -I")/include"
+  echo XLDFLAGS = -libpath:"$(optdirs:;=/lib" -libpath:")/lib"
+  echo !endif
+
+  if not "%pathlist%" == "" (
+    echo.
     call echo PATH = %%pathlist:;=/bin;%%$^(PATH^)
     call echo INCLUDE = %%pathlist:;=/include;%%$^(INCLUDE^)
     call echo LIB = %%pathlist:;=/lib;%%$^(LIB^)
   )
 ) >> %config_make%
-del %confargs% > nul
+
+del %confargs%
+if "%debug_configure%" == "yes" (type %config_make%)
 
 nmake -al -f %WIN32DIR%/setup.mak "WIN32DIR=%WIN32DIR%" ^
     config_make=%config_make% ^
-    MAKEFILE=Makefile.new MAKEFILE_BACK=Makefile.old MAKEFILE_NEW=Makefile
-:exit
-@endlocal
+    MAKEFILE=Makefile.new MAKEFILE_BACK=Makefile.old MAKEFILE_NEW=Makefile ^
+    %target%
+set error=%ERRORLEVEL%
+if exist %config_make% del /q %config_make%
diff --git a/win32/enc-setup.mak b/win32/enc-setup.mak
index 44345a2f45d6ed..b012161e3256cc 100644
--- a/win32/enc-setup.mak
+++ b/win32/enc-setup.mak
@@ -4,7 +4,7 @@ BUILTIN_ENCOBJS BUILTIN_TRANSOBJS: $(srcdir)/enc/Makefile.in
 !include $(srcdir)/enc/Makefile.in
 
 BUILTIN_ENCOBJS:
-	@echo BUILTIN_ENCOBJS = $(BUILTIN_ENCS:.c=.obj) >> $(MAKEFILE)
+	@echo>> $(MAKEFILE) BUILTIN_ENCOBJS = $(BUILTIN_ENCS:.c=.obj)
 
 BUILTIN_TRANSOBJS:
-	@echo BUILTIN_TRANSOBJS = $(BUILTIN_TRANSES:.trans=.obj) >> $(MAKEFILE)
+	@echo>> $(MAKEFILE) BUILTIN_TRANSOBJS = $(BUILTIN_TRANSES:.trans=.obj)
diff --git a/win32/setup.mak b/win32/setup.mak
index 6fc28ebafbc996..19ace3445c2568 100644
--- a/win32/setup.mak
+++ b/win32/setup.mak
@@ -22,7 +22,7 @@ MAKE = $(MAKE) -f $(MAKEFILE)
 MAKEFILE = Makefile
 !endif
 CPU = PROCESSOR_LEVEL
-CC = $(CC) -nologo -source-charset:utf-8
+CC = $(CC) -nologo
 CPP = $(CC) -EP
 !if "$(HAVE_BASERUBY)" != "no" && "$(BASERUBY)" == ""
 BASERUBY = ruby
@@ -35,13 +35,14 @@ i586-mswin32: -prologue- -i586- -epilogue-
 i686-mswin32: -prologue- -i686- -epilogue-
 alpha-mswin32: -prologue- -alpha- -epilogue-
 x64-mswin64: -prologue- -x64- -epilogue-
+arm64-mswin64: -prologue- -arm64- -epilogue-
 
 -prologue-: -basic-vars- -baseruby- -gmp-
 -generic-: -osname-
 
 -basic-vars-: nul
 	@rem <<$(MAKEFILE)
-### Makefile for ruby $(TARGET_OS) ###
+### Makefile for ruby ###
 MAKE = nmake
 srcdir = $(srcdir:\=/)
 prefix = $(prefix:\=/)
@@ -70,20 +71,31 @@ int main(void) {mpz_init(x); return 0;}
 	@echo # TARGET>>$(MAKEFILE)
 
 -osname32-: -osname-section-
-	@echo TARGET_OS = mswin32>>$(MAKEFILE)
+	@$(CPP) -Tc <<"checking if target OS is 32bit" >>$(MAKEFILE)
+#ifdef _WIN64
+#error
+#else
+TARGET_OS = mswin32
+#endif
+<<
 
 -osname64-: -osname-section-
-	@echo TARGET_OS = mswin64>>$(MAKEFILE)
+	@$(CPP) -Tc <<"checking if target OS is 64bit" >>$(MAKEFILE)
+#ifndef _WIN64
+#error
+#else
+TARGET_OS = mswin64
+#endif
+<<
 
 -osname-: -osname-section-
-	@echo !ifndef TARGET_OS>>$(MAKEFILE)
-	@($(CC) -c <<conftest.c > nul && (echo TARGET_OS = mswin32) || (echo TARGET_OS = mswin64)) >>$(MAKEFILE)
+	@$(CPP) -Tc <<"checking for target OS" 2>nul | findstr = >>$(MAKEFILE)
 #ifdef _WIN64
-#error
+TARGET_OS = mswin64
+#else
+TARGET_OS = mswin32
 #endif
 <<
-	@echo !endif>>$(MAKEFILE)
-	@$(WIN32DIR:/=\)\rm.bat conftest.*
 
 -compiler-: -compiler-section- -version- -runtime- -headers-
 
@@ -211,27 +223,54 @@ del %0 & exit
 <<
 
 -generic-: nul
-	@$(CPP) <<conftest.c 2>nul | findstr = >>$(MAKEFILE)
+	@$(CPP) -Tc <<checking-target 2>nul | findstr = >>$(MAKEFILE)
 #if defined _M_ARM64
 MACHINE = arm64
 #elif defined _M_X64
 MACHINE = x64
 #else
 MACHINE = x86
-#endif
-<<
 !if defined($(CPU))
-	@echo>>$(MAKEFILE) $(CPU) = $(PROCESSOR_LEVEL)
+$(CPU) = $(PROCESSOR_LEVEL)
 !endif
+#endif
 
 -alpha-: -osname32-
-	@echo MACHINE = alpha>>$(MAKEFILE)
+	@$(CPP) -Tc <<"checking if compiler is for $(@:-=)" >>$(MAKEFILE)
+#ifndef _M_ALPHA
+#error Not compiler for $(@:-=)
+#else
+MACHINE = $(@:-=)
+#endif
+<<
+
 -x64-: -osname64-
-	@echo MACHINE = x64>>$(MAKEFILE)
+	@$(CPP) -Tc <<"checking if compiler is for $(@:-=)" >>$(MAKEFILE)
+#ifndef _M_AMD64
+#error Not compiler for $(@:-=)
+#else
+MACHINE = $(@:-=)
+#endif
+<<
+
 -ix86-: -osname32-
-	@echo MACHINE = x86>>$(MAKEFILE)
+	@$(CPP) -Tc <<"checking if compiler is for $(@:-=)" >>$(MAKEFILE)
+#ifndef _M_IX86
+#error Not compiler for $(@:-=)
+#else
+#define ix86 x86
+MACHINE = $(@:-=)
+#endif
+<<
+
 -arm64-: -osname64-
-	@echo MACHINE = arm64>>$(MAKEFILE)
+	@$(CPP) -Tc <<"checking if compiler is for $(@:-=)" >>$(MAKEFILE)
+#ifndef _M_ARM64
+#error Not compiler for $(@:-=)
+#else
+MACHINE = $(@:-=)
+#endif
+<<
 
 -i386-: -ix86-
 	@echo $(CPU) = 3>>$(MAKEFILE)
@@ -261,7 +300,7 @@ MACHINE = x86
 # XLDFLAGS =
 # RFLAGS = -r
 # EXTLIBS =
-CC = $(CC)
+CC = $(CC) -source-charset:utf-8
 !if "$(AS)" != "ml64"
 AS = $(AS) -nologo
 !endif
@@ -277,5 +316,5 @@ $(BANG)include $$(srcdir)/win32/Makefile.sub
 <<
 	@$(COMSPEC) /C $(srcdir:/=\)\win32\rm.bat config.h config.status
 	-@move /y $(MAKEFILE_NEW) $(MAKEFILE_BACK) > nul 2> nul
-	@ren $(MAKEFILE) $(MAKEFILE_NEW)
+	@move /y $(MAKEFILE) $(MAKEFILE_NEW) > nul
 	@echo type 'nmake' to make ruby.