diff --git a/NEWS.md b/NEWS.md
index 064263c115277a..e043d15bea9742 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -101,7 +101,7 @@ releases.
 * ipaddr 1.2.9
   * 1.2.8 to [v1.2.9][ipaddr-v1.2.9]
 * json 2.21.0
-  * 2.18.0 to [v2.18.1][json-v2.18.1], [v2.19.0][json-v2.19.0], [v2.19.1][json-v2.19.1], [v2.19.2][json-v2.19.2], [v2.19.3][json-v2.19.3], [v2.19.4][json-v2.19.4], [v2.19.5][json-v2.19.5], [v2.19.6][json-v2.19.6], [v2.19.7][json-v2.19.7], [v2.19.8][json-v2.19.8], [v2.19.9][json-v2.19.9], [v2.20.0][json-v2.20.0]
+  * 2.18.0 to [v2.18.1][json-v2.18.1], [v2.19.0][json-v2.19.0], [v2.19.1][json-v2.19.1], [v2.19.2][json-v2.19.2], [v2.19.3][json-v2.19.3], [v2.19.4][json-v2.19.4], [v2.19.5][json-v2.19.5], [v2.19.6][json-v2.19.6], [v2.19.7][json-v2.19.7], [v2.19.8][json-v2.19.8], [v2.19.9][json-v2.19.9], [v2.20.0][json-v2.20.0], [v2.21.0][json-v2.21.0]
 * openssl 4.0.2
   * 4.0.0 to [v4.0.1][openssl-v4.0.1], [v4.0.2][openssl-v4.0.2]
 * pp 0.6.4
@@ -270,6 +270,7 @@ A lot of work has gone into making Ractors more stable, performant, and usable.
 [json-v2.19.8]: https://github.com/ruby/json/releases/tag/v2.19.8
 [json-v2.19.9]: https://github.com/ruby/json/releases/tag/v2.19.9
 [json-v2.20.0]: https://github.com/ruby/json/releases/tag/v2.20.0
+[json-v2.21.0]: https://github.com/ruby/json/releases/tag/v2.21.0
 [openssl-v4.0.1]: https://github.com/ruby/openssl/releases/tag/v4.0.1
 [openssl-v4.0.2]: https://github.com/ruby/openssl/releases/tag/v4.0.2
 [pp-v0.6.4]: https://github.com/ruby/pp/releases/tag/v0.6.4
diff --git a/ext/stringio/stringio.c b/ext/stringio/stringio.c
index c91bf3d6e22857..3fecb09e7e35b7 100644
--- a/ext/stringio/stringio.c
+++ b/ext/stringio/stringio.c
@@ -116,6 +116,10 @@ strio_memsize(const void *p)
     return sizeof(struct StringIO);
 }
 
+#ifndef RUBY_TYPED_THREAD_SAFE_FREE
+#define RUBY_TYPED_THREAD_SAFE_FREE RUBY_TYPED_FREE_IMMEDIATELY
+#endif
+
 static const rb_data_type_t strio_data_type = {
     "strio",
     {
@@ -123,7 +127,7 @@ static const rb_data_type_t strio_data_type = {
 	strio_free,
 	strio_memsize,
     },
-    0, 0, RUBY_TYPED_FREE_IMMEDIATELY | RUBY_TYPED_WB_PROTECTED
+    0, 0, RUBY_TYPED_THREAD_SAFE_FREE | RUBY_TYPED_WB_PROTECTED
 };
 
 #define check_strio(self) ((struct StringIO*)rb_check_typeddata((self), &strio_data_type))
diff --git a/ext/strscan/strscan.c b/ext/strscan/strscan.c
index dede57218bd173..da02291478c3c4 100644
--- a/ext/strscan/strscan.c
+++ b/ext/strscan/strscan.c
@@ -238,6 +238,10 @@ strscan_memsize(const void *ptr)
     return size;
 }
 
+#ifndef RUBY_TYPED_THREAD_SAFE_FREE
+#define RUBY_TYPED_THREAD_SAFE_FREE RUBY_TYPED_FREE_IMMEDIATELY
+#endif
+
 static const rb_data_type_t strscanner_type = {
     .wrap_struct_name = "StringScanner",
     .function = {
@@ -248,7 +252,7 @@ static const rb_data_type_t strscanner_type = {
         .dcompact = strscan_compact,
 #endif
     },
-    .flags = RUBY_TYPED_FREE_IMMEDIATELY | RUBY_TYPED_WB_PROTECTED | RUBY_TYPED_EMBEDDABLE
+    .flags = RUBY_TYPED_THREAD_SAFE_FREE | RUBY_TYPED_WB_PROTECTED | RUBY_TYPED_EMBEDDABLE
 };
 
 static VALUE
diff --git a/spec/ruby/core/integer/bit_count_spec.rb b/spec/ruby/core/integer/bit_count_spec.rb
index 6fa06154aae588..c596a533661397 100644
--- a/spec/ruby/core/integer/bit_count_spec.rb
+++ b/spec/ruby/core/integer/bit_count_spec.rb
@@ -21,11 +21,11 @@
     end
 
     it "raises an ArgumentError for a negative number" do
-      -> { -1.bit_count }.should raise_error(ArgumentError)
-      -> { -19.bit_count }.should raise_error(ArgumentError)
-      -> { fixnum_min.bit_count }.should raise_error(ArgumentError)
-      -> { (-2**1000).bit_count }.should raise_error(ArgumentError)
-      -> { (-2**1000 - 1).bit_count }.should raise_error(ArgumentError)
+      -> { -1.bit_count }.should.raise(ArgumentError)
+      -> { -19.bit_count }.should.raise(ArgumentError)
+      -> { fixnum_min.bit_count }.should.raise(ArgumentError)
+      -> { (-2**1000).bit_count }.should.raise(ArgumentError)
+      -> { (-2**1000 - 1).bit_count }.should.raise(ArgumentError)
     end
   end
 end
diff --git a/win32/rm.bat b/win32/rm.bat
index 8d5aaba14734df..250cee02c1e42c 100755
--- a/win32/rm.bat
+++ b/win32/rm.bat
@@ -57,11 +57,23 @@ goto :remove_end
     ::- files under the target directory, instead of the symlink itself.
     rd /q "%p%" 2> nul && goto :remove_end
 
+    ::- If matching files and directory exist, remove the files only first.
+    del /q "%p%" 2> nul
+
     ::- `del` exits with 0 even when nothing matched, so its result cannot
-    ::- tell whether directories remain; remove them first.
-    if "%recursive%" == "-r" for /D %%I in (%p%) do (
-        rd /s /q %%I || call set error=%%ERRORLEVEL%%
+    ::- tell whether directories remain; check if matching entries still
+    ::- exist instead.
+    if not exist "%p%" goto :remove_end
+
+    ::- Unless `-r` option is given, do not remove directories; just fail.
+    if not "%recursive%" == "-r" (
+        call set error=1
+        goto :remove_end
+    )
+
+    ::- Remove remained directories recursively.
+    for /D %%I in (%p%) do (
+        rd /s /q %%I 2> nul || call set error=%%ERRORLEVEL%%
     )
-    if exist "%p%" del /q "%p%" 2> nul
 :remove_end
 endlocal & set "error=%error%" & goto :EOF