diff --git a/lib/bundled_gems.rb b/lib/bundled_gems.rb
index b1e5470fc7..e3d2617457 100644
--- a/lib/bundled_gems.rb
+++ b/lib/bundled_gems.rb
@@ -26,23 +26,18 @@ module Gem::BUNDLED_GEMS
     "resolv-replace" => "3.4.0",
     "rinda" => "3.4.0",
     "syslog" => "3.4.0",
+    "ostruct" => "3.5.0",
+    "pstore" => "3.5.0",
+    "rdoc" => "3.5.0",
+    "win32ole" => "3.5.0",
+    "fiddle" => "3.5.0",
+    "logger" => "3.5.0",
   }.freeze
 
   SINCE_FAST_PATH = SINCE.transform_keys { |g| g.sub(/\A.*\-/, "") }.freeze
 
   EXACT = {
-    "abbrev" => true,
-    "base64" => true,
-    "bigdecimal" => true,
-    "csv" => true,
-    "drb" => true,
-    "getoptlong" => true,
-    "mutex_m" => true,
-    "nkf" => true, "kconv" => "nkf",
-    "observer" => true,
-    "resolv-replace" => true,
-    "rinda" => true,
-    "syslog" => true,
+    "kconv" => "nkf",
   }.freeze
 
   PREFIXED = {
@@ -70,8 +65,12 @@ module Gem::BUNDLED_GEMS
     [::Kernel.singleton_class, ::Kernel].each do |kernel_class|
       kernel_class.send(:alias_method, :no_warning_require, :require)
       kernel_class.send(:define_method, :require) do |name|
-        if message = ::Gem::BUNDLED_GEMS.warning?(name, specs: spec_names) # rubocop:disable Style/HashSyntax
-          warn message, :uplevel => 1
+        if message = ::Gem::BUNDLED_GEMS.warning?(name, specs: spec_names)
+          if ::Gem::BUNDLED_GEMS.uplevel > 0
+            Kernel.warn message, uplevel: ::Gem::BUNDLED_GEMS.uplevel
+          else
+            Kernel.warn message
+          end
         end
         kernel_class.send(:no_warning_require, name)
       end
@@ -83,6 +82,36 @@ module Gem::BUNDLED_GEMS
     end
   end
 
+  def self.uplevel
+    frame_count = 0
+    frames_to_skip = 3
+    uplevel = 0
+    require_found = false
+    Thread.each_caller_location do |cl|
+      frame_count += 1
+      if frames_to_skip >= 1
+        frames_to_skip -= 1
+        next
+      end
+      uplevel += 1
+      if require_found
+        if cl.base_label != "require"
+          return uplevel
+        end
+      else
+        if cl.base_label == "require"
+          require_found = true
+        end
+      end
+      # Don't show script name when bundle exec and call ruby script directly.
+      if cl.path.end_with?("bundle")
+        frame_count = 0
+        break
+      end
+    end
+    require_found ? 1 : frame_count - 1
+  end
+
   def self.find_gem(path)
     if !path
       return
@@ -93,7 +122,7 @@ module Gem::BUNDLED_GEMS
     else
       return
     end
-    EXACT[n] or PREFIXED[n = n[%r[\A[^/]+(?=/)]]] && n
+    (EXACT[n] || !!SINCE[n]) or PREFIXED[n = n[%r[\A[^/]+(?=/)]]] && n
   end
 
   def self.warning?(name, specs: nil)
@@ -108,7 +137,7 @@ module Gem::BUNDLED_GEMS
       # We'll fail to warn requires for files that are not the entry point
       # of the gem, e.g. require "logger/formatter.rb" won't warn.
       # But that's acceptable because this warning is best effort,
-      # and in the overwhelming majority of case logger.rb will end
+      # and in the overwhelming majority of cases logger.rb will end
       # up required.
       return unless SINCE_FAST_PATH[File.basename(feature, ".*")]
     else
@@ -148,29 +177,35 @@ module Gem::BUNDLED_GEMS
   end
 
   def self.build_message(gem)
-    msg = " #{RUBY_VERSION < SINCE[gem] ? "will no longer be" : "is not"} part of the default gems since Ruby #{SINCE[gem]}."
+    msg = " #{RUBY_VERSION < SINCE[gem] ? "will no longer be" : "is not"} part of the default gems starting from Ruby #{SINCE[gem]}."
 
     if defined?(Bundler)
-      msg += " Add #{gem} to your Gemfile or gemspec."
+      msg += "\nYou can add #{gem} to your Gemfile or gemspec to silence this warning."
 
-      # We detect the gem name from caller_locations. We need to skip 2 frames like:
-      # lib/ruby/3.3.0+0/bundled_gems.rb:90:in `warning?'",
-      # lib/ruby/3.3.0+0/bundler/rubygems_integration.rb:247:in `block (2 levels) in replace_require'",
+      # We detect the gem name from caller_locations. First we walk until we find `require`
+      # then take the first frame that's not from `require`.
       #
       # Additionally, we need to skip Bootsnap and Zeitwerk if present, these
       # gems decorate Kernel#require, so they are not really the ones issuing
       # the require call users should be warned about. Those are upwards.
-      frames_to_skip = 2
+      frames_to_skip = 3
       location = nil
+      require_found = false
       Thread.each_caller_location do |cl|
         if frames_to_skip >= 1
           frames_to_skip -= 1
           next
         end
 
-        if cl.base_label != "require"
-          location = cl.path
-          break
+        if require_found
+          if cl.base_label != "require"
+            location = cl.path
+            break
+          end
+        else
+          if cl.base_label == "require"
+            require_found = true
+          end
         end
       end
 
@@ -183,7 +218,7 @@ module Gem::BUNDLED_GEMS
           end
         end
         if caller_gem
-          msg += " Also contact author of #{caller_gem} to add #{gem} into its gemspec."
+          msg += "\nAlso please contact the author of #{caller_gem} to request adding #{gem} into its gemspec."
         end
       end
     else
@@ -204,7 +239,7 @@ class LoadError
 
     name = path.tr("/", "-")
     if !defined?(Bundler) && Gem::BUNDLED_GEMS::SINCE[name] && !Gem::BUNDLED_GEMS::WARNED[name]
-      warn name + Gem::BUNDLED_GEMS.build_message(name)
+      warn name + Gem::BUNDLED_GEMS.build_message(name), uplevel: Gem::BUNDLED_GEMS.uplevel
     end
     super
   end
diff --git a/tool/test_for_warn_bundled_gems/test.sh b/tool/test_for_warn_bundled_gems/test.sh
index a14d5bcedc..0cd65f07e8 100755
--- a/tool/test_for_warn_bundled_gems/test.sh
+++ b/tool/test_for_warn_bundled_gems/test.sh
@@ -51,3 +51,7 @@ echo
 echo "* Don't show warning bigdecimal/util when bigdecimal on Gemfile"
 ruby test_no_warn_sub_feature.rb
 echo
+
+echo "* Show warning when warn is not the standard one in the current scope"
+ruby test_warn_redefined.rb
+echo
diff --git a/tool/test_for_warn_bundled_gems/test_warn_redefined.rb b/tool/test_for_warn_bundled_gems/test_warn_redefined.rb
new file mode 100644
index 0000000000..a898a8c07c
--- /dev/null
+++ b/tool/test_for_warn_bundled_gems/test_warn_redefined.rb
@@ -0,0 +1,18 @@
+module My
+  def warn(msg)
+  end
+
+  def my
+    require "bundler/inline"
+
+    gemfile do
+      source "https://rubygems.org"
+    end
+
+    require "csv"
+  end
+
+  extend self
+end
+
+My.my