diff --git a/.github/workflows/windows-test.yaml b/.github/workflows/windows-test.yaml
index 1f43f18e57..12a7537c57 100644
--- a/.github/workflows/windows-test.yaml
+++ b/.github/workflows/windows-test.yaml
@@ -13,11 +13,14 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        ruby-version: ['2.7', '2.6']
+        ruby-version: ['3.1', '2.7']
         os:
           - windows-latest
         experimental: [false]
         include:
+          - ruby-version: head
+            os: windows-latest
+            experimental: true
           - ruby-version: '3.0.3'
             os: windows-latest
             experimental: false
diff --git a/lib/fluent/plugin/file_wrapper.rb b/lib/fluent/plugin/file_wrapper.rb
index 57d6b4949d..f05af89205 100644
--- a/lib/fluent/plugin/file_wrapper.rb
+++ b/lib/fluent/plugin/file_wrapper.rb
@@ -16,8 +16,35 @@
 
 module Fluent
   module FileWrapper
-    def self.open(*args)
-      io = WindowsFile.new(*args).io
+    include File::Constants
+
+    def self.mode2flags(mode)
+      # Always need BINARY to enable SHARE_DELETE
+      # https://bugs.ruby-lang.org/issues/11218
+      # https://github.com/ruby/ruby/blob/d6684f063bc53e3cab025bd39526eca3b480b5e7/win32/win32.c#L6332-L6345
+      flags = BINARY | SHARE_DELETE
+      case mode.delete("b")
+      when "r"
+        flags |= RDONLY
+      when "r+"
+        flags |= RDWR
+      when "w"
+        flags |= WRONLY | CREAT | TRUNC
+      when "w+"
+        flags |= RDWR | CREAT | TRUNC
+      when "a"
+        flags |= WRONLY | CREAT | APPEND
+      when "a+"
+        flags |= RDWR | CREAT | APPEND
+      else
+        raise Errno::EINVAL.new("Unsupported mode by Fluent::FileWrapper: #{mode}")
+      end
+    end
+
+    def self.open(path, mode='r')
+      # inject File::Constants::SHARE_DELETE
+      # https://github.com/fluent/fluentd/pull/3585#issuecomment-1101502617
+      io = File.open(path, mode2flags(mode))
       if block_given?
         v = yield io
         io.close
@@ -35,17 +62,6 @@ def self.stat(path)
     end
   end
 
-  module WindowsFileExtension
-    attr_reader :path
-
-    def stat
-      s = super
-      s.instance_variable_set :@ino, @ino
-      def s.ino; @ino; end
-      s
-    end
-  end
-
   class Win32Error < StandardError
     require 'windows/error'
     include Windows::Error
@@ -88,7 +104,9 @@ def wsaerr?
     end
   end
 
-  # To open and get stat with setting FILE_SHARE_DELETE
+  # To open and get stat with setting FILE_SHARE_DELETE.
+  # Although recent Ruby's File.stat uses it, we still need this to keep
+  # backward compatibility of ino and delete_pending methods.
   class WindowsFile
     require 'windows/file'
     require 'windows/error'
@@ -135,16 +153,6 @@ def close
       @file_handle = INVALID_HANDLE_VALUE
     end
 
-    def io
-      fd = _open_osfhandle(@file_handle, 0)
-      raise Errno::ENOENT if fd == -1
-      io = File.for_fd(fd, @mode)
-      io.instance_variable_set :@ino, self.ino
-      io.instance_variable_set :@path, @path
-      io.extend WindowsFileExtension
-      io
-    end
-
     def ino
       by_handle_file_information = '\0'*(4+8+8+8+4+4+4+4+4+4)   #72bytes
 
diff --git a/test/plugin/test_out_forward.rb b/test/plugin/test_out_forward.rb
index 53aca518c2..66a2776cc5 100644
--- a/test/plugin/test_out_forward.rb
+++ b/test/plugin/test_out_forward.rb
@@ -431,10 +431,12 @@ def try_write(chunk)
     ]
 
     stub(d.instance.ack_handler).read_ack_from_sock(anything).never
-    target_input_driver.run(expect_records: 2) do
-      d.run do
-        emit_events.each do |tag, t, record|
-          d.feed(tag, t, record)
+    assert_rr do
+      target_input_driver.run(expect_records: 2) do
+        d.run do
+          emit_events.each do |tag, t, record|
+            d.feed(tag, t, record)
+          end
         end
       end
     end
@@ -461,10 +463,12 @@ def try_write(chunk)
     ]
 
     stub(d.instance.ack_handler).read_ack_from_sock(anything).never
-    target_input_driver.run(expect_records: 2) do
-      d.run(default_tag: 'test') do
-        records.each do |record|
-          d.feed(time, record)
+    assert_rr do
+      target_input_driver.run(expect_records: 2) do
+        d.run(default_tag: 'test') do
+          records.each do |record|
+            d.feed(time, record)
+          end
         end
       end
     end
@@ -491,10 +495,12 @@ def try_write(chunk)
       {"a" => 2}
     ]
     stub(d.instance.ack_handler).read_ack_from_sock(anything).never
-    target_input_driver.run(expect_records: 2) do
-      d.run(default_tag: 'test') do
-        records.each do |record|
-          d.feed(time, record)
+    assert_rr do
+      target_input_driver.run(expect_records: 2) do
+        d.run(default_tag: 'test') do
+          records.each do |record|
+            d.feed(time, record)
+          end
         end
       end
     end
@@ -549,10 +555,12 @@ def try_write(chunk)
     ]
     # not attempt to receive responses
     stub(d.instance.ack_handler).read_ack_from_sock(anything).never
-    target_input_driver.run(expect_records: 2) do
-      d.run(default_tag: 'test') do
-        records.each do |record|
-          d.feed(time, record)
+    assert_rr do
+      target_input_driver.run(expect_records: 2) do
+        d.run(default_tag: 'test') do
+          records.each do |record|
+            d.feed(time, record)
+          end
         end
       end
     end
@@ -575,10 +583,12 @@ def try_write(chunk)
     ]
     # not attempt to receive responses
     stub(d.instance.ack_handler).read_ack_from_sock(anything).never
-    target_input_driver.run(expect_records: 2) do
-      d.run(default_tag: 'test') do
-        records.each do |record|
-          d.feed(time, record)
+    assert_rr do
+      target_input_driver.run(expect_records: 2) do
+        d.run(default_tag: 'test') do
+          records.each do |record|
+            d.feed(time, record)
+          end
         end
       end
     end