From d9b03c9369001a835b186ee7fd637e7f94d3d64f Mon Sep 17 00:00:00 2001
From: Benoit Daloze <eregontp@gmail.com>
Date: Tue, 16 Dec 2025 15:39:00 +0100
Subject: [PATCH 01/14] [ruby/prism] Fix assertions in location_test.rb

* assert_raise's 2nd argument is the failure message,
  shown when the expected exception is not raised.
  It's not the expected message.
  See https://github.com/test-unit/test-unit/issues/347

https://github.com/ruby/prism/commit/e3df994d47
---
 test/prism/ruby/location_test.rb | 9 ++++++---
 1 file changed, 6 insertions(+), 3 deletions(-)

diff --git a/test/prism/ruby/location_test.rb b/test/prism/ruby/location_test.rb
index 33f844243c0547..5e2ab63802b1f5 100644
--- a/test/prism/ruby/location_test.rb
+++ b/test/prism/ruby/location_test.rb
@@ -13,19 +13,22 @@ def test_join
       assert_equal 0, joined.start_offset
       assert_equal 10, joined.length
 
-      assert_raise(RuntimeError, "Incompatible locations") do
+      e = assert_raise(RuntimeError) do
         argument.location.join(receiver.location)
       end
+      assert_equal "Incompatible locations", e.message
 
       other_argument = Prism.parse_statement("1234 + 567").arguments.arguments.first
 
-      assert_raise(RuntimeError, "Incompatible sources") do
+      e = assert_raise(RuntimeError) do
         other_argument.location.join(receiver.location)
       end
+      assert_equal "Incompatible sources", e.message
 
-      assert_raise(RuntimeError, "Incompatible sources") do
+      e = assert_raise(RuntimeError) do
         receiver.location.join(other_argument.location)
       end
+      assert_equal "Incompatible sources", e.message
     end
 
     def test_character_offsets

From 76248400b75d42288a5941aa03e2d2e6d4fac057 Mon Sep 17 00:00:00 2001
From: Earlopain <14981592+Earlopain@users.noreply.github.com>
Date: Wed, 17 Dec 2025 10:47:43 +0100
Subject: [PATCH 02/14] [ruby/prism] Add Ruby 4.1 as a version specifier

https://github.com/ruby/prism/commit/138db9ccc4
---
 lib/prism/ffi.rb                        |  2 ++
 lib/prism/prism.gemspec                 |  2 ++
 lib/prism/translation.rb                |  1 +
 lib/prism/translation/parser.rb         |  4 +++-
 lib/prism/translation/parser41.rb       | 13 +++++++++++++
 lib/prism/translation/parser_current.rb |  2 ++
 prism/options.c                         | 10 ++++++++++
 prism/options.h                         |  5 ++++-
 test/prism/api/parse_test.rb            |  3 +++
 test/prism/test_helper.rb               |  2 +-
 10 files changed, 41 insertions(+), 3 deletions(-)
 create mode 100644 lib/prism/translation/parser41.rb

diff --git a/lib/prism/ffi.rb b/lib/prism/ffi.rb
index 7e6103fde775bf..d4c9d60c9aa2a4 100644
--- a/lib/prism/ffi.rb
+++ b/lib/prism/ffi.rb
@@ -434,6 +434,8 @@ def dump_options_version(version)
         2
       when /\A3\.5(\.\d+)?\z/, /\A4\.0(\.\d+)?\z/
         3
+      when /\A4\.1(\.\d+)?\z/
+        4
       else
         if current
           raise CurrentVersionError, RUBY_VERSION
diff --git a/lib/prism/prism.gemspec b/lib/prism/prism.gemspec
index 10c2eaad209ed4..d9872f88acffd9 100644
--- a/lib/prism/prism.gemspec
+++ b/lib/prism/prism.gemspec
@@ -102,6 +102,7 @@ Gem::Specification.new do |spec|
     "lib/prism/translation/parser34.rb",
     "lib/prism/translation/parser35.rb",
     "lib/prism/translation/parser40.rb",
+    "lib/prism/translation/parser41.rb",
     "lib/prism/translation/parser/builder.rb",
     "lib/prism/translation/parser/compiler.rb",
     "lib/prism/translation/parser/lexer.rb",
@@ -125,6 +126,7 @@ Gem::Specification.new do |spec|
     "rbi/prism/translation/parser34.rbi",
     "rbi/prism/translation/parser35.rbi",
     "rbi/prism/translation/parser40.rbi",
+    "rbi/prism/translation/parser41.rbi",
     "rbi/prism/translation/ripper.rbi",
     "rbi/prism/visitor.rbi",
     "sig/prism.rbs",
diff --git a/lib/prism/translation.rb b/lib/prism/translation.rb
index 7933b4a7222e93..89c70ee420130f 100644
--- a/lib/prism/translation.rb
+++ b/lib/prism/translation.rb
@@ -11,6 +11,7 @@ module Translation # steep:ignore
     autoload :Parser34, "prism/translation/parser34"
     autoload :Parser35, "prism/translation/parser35"
     autoload :Parser40, "prism/translation/parser40"
+    autoload :Parser41, "prism/translation/parser41"
     autoload :Ripper, "prism/translation/ripper"
     autoload :RubyParser, "prism/translation/ruby_parser"
   end
diff --git a/lib/prism/translation/parser.rb b/lib/prism/translation/parser.rb
index 23245dc383e9e9..fed4ac4cd1f0fd 100644
--- a/lib/prism/translation/parser.rb
+++ b/lib/prism/translation/parser.rb
@@ -84,7 +84,7 @@ def initialize(builder = Prism::Translation::Parser::Builder.new, parser: Prism)
       end
 
       def version # :nodoc:
-        40
+        41
       end
 
       # The default encoding for Ruby files is UTF-8.
@@ -358,6 +358,8 @@ def convert_for_prism(version)
           "3.4.0"
         when 35, 40
           "4.0.0"
+        when 41
+          "4.1.0"
         else
           "latest"
         end
diff --git a/lib/prism/translation/parser41.rb b/lib/prism/translation/parser41.rb
new file mode 100644
index 00000000000000..ed819064004606
--- /dev/null
+++ b/lib/prism/translation/parser41.rb
@@ -0,0 +1,13 @@
+# frozen_string_literal: true
+# :markup: markdown
+
+module Prism
+  module Translation
+    # This class is the entry-point for Ruby 4.1 of `Prism::Translation::Parser`.
+    class Parser41 < Parser
+      def version # :nodoc:
+        41
+      end
+    end
+  end
+end
diff --git a/lib/prism/translation/parser_current.rb b/lib/prism/translation/parser_current.rb
index 76d71e940926cc..ac6daf7082e416 100644
--- a/lib/prism/translation/parser_current.rb
+++ b/lib/prism/translation/parser_current.rb
@@ -12,6 +12,8 @@ module Translation
       ParserCurrent = Parser34
     when /^3\.5\./, /^4\.0\./
       ParserCurrent = Parser40
+    when /^4\.1\./
+      ParserCurrent = Parser41
     else
       # Keep this in sync with released Ruby.
       parser = Parser34
diff --git a/prism/options.c b/prism/options.c
index 4a8953da7d2aac..09d2a65a6cbcf6 100644
--- a/prism/options.c
+++ b/prism/options.c
@@ -93,6 +93,11 @@ pm_options_version_set(pm_options_t *options, const char *version, size_t length
             return true;
         }
 
+        if (strncmp(version, "4.1", 3) == 0) {
+            options->version = PM_OPTIONS_VERSION_CRUBY_4_1;
+            return true;
+        }
+
         return false;
     }
 
@@ -111,6 +116,11 @@ pm_options_version_set(pm_options_t *options, const char *version, size_t length
             options->version = PM_OPTIONS_VERSION_CRUBY_4_0;
             return true;
         }
+
+        if (strncmp(version, "4.1.", 4) == 0) {
+            options->version = PM_OPTIONS_VERSION_CRUBY_4_1;
+            return true;
+        }
     }
 
     if (length >= 6) {
diff --git a/prism/options.h b/prism/options.h
index a663c9767e994e..c00c7bf7553a4f 100644
--- a/prism/options.h
+++ b/prism/options.h
@@ -97,8 +97,11 @@ typedef enum {
     /** The vendored version of prism in CRuby 4.0.x. */
     PM_OPTIONS_VERSION_CRUBY_4_0 = 3,
 
+    /** The vendored version of prism in CRuby 4.1.x. */
+    PM_OPTIONS_VERSION_CRUBY_4_1 = 4,
+
     /** The current version of prism. */
-    PM_OPTIONS_VERSION_LATEST = PM_OPTIONS_VERSION_CRUBY_4_0
+    PM_OPTIONS_VERSION_LATEST = PM_OPTIONS_VERSION_CRUBY_4_1
 } pm_options_version_t;
 
 /**
diff --git a/test/prism/api/parse_test.rb b/test/prism/api/parse_test.rb
index bb1761109fadbb..bbf28201ffe2b4 100644
--- a/test/prism/api/parse_test.rb
+++ b/test/prism/api/parse_test.rb
@@ -122,6 +122,9 @@ def test_version
       assert Prism.parse_success?("1 + 1", version: "4.0")
       assert Prism.parse_success?("1 + 1", version: "4.0.0")
 
+      assert Prism.parse_success?("1 + 1", version: "4.1")
+      assert Prism.parse_success?("1 + 1", version: "4.1.0")
+
       assert Prism.parse_success?("1 + 1", version: "latest")
 
       # Test edge case
diff --git a/test/prism/test_helper.rb b/test/prism/test_helper.rb
index f78e68e87c107a..43771110b4284f 100644
--- a/test/prism/test_helper.rb
+++ b/test/prism/test_helper.rb
@@ -241,7 +241,7 @@ def self.windows?
     end
 
     # All versions that prism can parse
-    SYNTAX_VERSIONS = %w[3.3 3.4 4.0]
+    SYNTAX_VERSIONS = %w[3.3 3.4 4.0 4.1]
 
     # `RUBY_VERSION` with the patch version excluded
     CURRENT_MAJOR_MINOR = RUBY_VERSION.split(".")[0, 2].join(".")

From e2c886dd669dd640dae75e3ac6d7206b74870d1b Mon Sep 17 00:00:00 2001
From: Earlopain <14981592+Earlopain@users.noreply.github.com>
Date: Mon, 1 Dec 2025 21:13:25 +0100
Subject: [PATCH 03/14] [ruby/prism] Reject `p(p a, &block => value)` and
 similar

Redo of https://github.com/ruby/prism/pull/3669 with more tests

https://github.com/ruby/prism/commit/48b403ea79
---
 prism/prism.c                                 | 26 ++++++++++-
 test/prism/errors/command_calls_35.txt        | 46 +++++++++++++++++++
 test/prism/fixtures/command_method_call_3.txt | 19 ++++++++
 3 files changed, 90 insertions(+), 1 deletion(-)
 create mode 100644 test/prism/errors/command_calls_35.txt
 create mode 100644 test/prism/fixtures/command_method_call_3.txt

diff --git a/prism/prism.c b/prism/prism.c
index f98032cd73b0b1..4c8ab91f0ef4e6 100644
--- a/prism/prism.c
+++ b/prism/prism.c
@@ -13412,6 +13412,30 @@ parse_assocs(pm_parser_t *parser, pm_static_literals_t *literals, pm_node_t *nod
     return contains_keyword_splat;
 }
 
+static inline bool
+argument_allowed_for_bare_hash(pm_parser_t *parser, pm_node_t *argument) {
+    if (pm_symbol_node_label_p(argument)) {
+        return true;
+    }
+
+    switch (PM_NODE_TYPE(argument)) {
+        case PM_CALL_NODE: {
+            pm_call_node_t *cast = (pm_call_node_t *) argument;
+            if (cast->opening_loc.start == NULL && cast->arguments != NULL) {
+                if (PM_NODE_FLAG_P(cast->arguments, PM_ARGUMENTS_NODE_FLAGS_CONTAINS_KEYWORDS | PM_ARGUMENTS_NODE_FLAGS_CONTAINS_SPLAT)) {
+                    return false;
+                }
+                if (cast->block != NULL) {
+                    return false;
+                }
+            }
+            break;
+        }
+        default: break;
+    }
+    return accept1(parser, PM_TOKEN_EQUAL_GREATER);
+}
+
 /**
  * Append an argument to a list of arguments.
  */
@@ -13569,7 +13593,7 @@ parse_arguments(pm_parser_t *parser, pm_arguments_t *arguments, bool accepts_for
                 bool contains_keywords = false;
                 bool contains_keyword_splat = false;
 
-                if (pm_symbol_node_label_p(argument) || accept1(parser, PM_TOKEN_EQUAL_GREATER)) {
+                if (argument_allowed_for_bare_hash(parser, argument)){
                     if (parsed_bare_hash) {
                         pm_parser_err_previous(parser, PM_ERR_ARGUMENT_BARE_HASH);
                     }
diff --git a/test/prism/errors/command_calls_35.txt b/test/prism/errors/command_calls_35.txt
new file mode 100644
index 00000000000000..45f569b117c6c5
--- /dev/null
+++ b/test/prism/errors/command_calls_35.txt
@@ -0,0 +1,46 @@
+p(p a, x: b => value)
+            ^~ unexpected '=>'; expected a `)` to close the arguments
+                    ^ unexpected ')', expecting end-of-input
+                    ^ unexpected ')', ignoring it
+
+p(p a, x: => value)
+          ^~ unexpected '=>'; expected a `)` to close the arguments
+                  ^ unexpected ')', expecting end-of-input
+                  ^ unexpected ')', ignoring it
+
+p(p a, &block => value)
+              ^~ unexpected '=>'; expected a `)` to close the arguments
+                      ^ unexpected ')', expecting end-of-input
+                      ^ unexpected ')', ignoring it
+
+p(p a do end => value)
+             ^~ unexpected '=>'; expected a `)` to close the arguments
+                     ^ unexpected ')', expecting end-of-input
+                     ^ unexpected ')', ignoring it
+
+p(p a, *args => value)
+             ^~ unexpected '=>'; expected a `)` to close the arguments
+                     ^ unexpected ')', expecting end-of-input
+                     ^ unexpected ')', ignoring it
+
+p(p a, **kwargs => value)
+                ^~ unexpected '=>'; expected a `)` to close the arguments
+                        ^ unexpected ')', expecting end-of-input
+                        ^ unexpected ')', ignoring it
+
+p p 1, &block => 2, &block
+              ^~ unexpected '=>', expecting end-of-input
+              ^~ unexpected '=>', ignoring it
+                  ^ unexpected ',', expecting end-of-input
+                  ^ unexpected ',', ignoring it
+                    ^ unexpected '&', ignoring it
+
+p p p 1 => 2 => 3 => 4
+                  ^~ unexpected '=>', expecting end-of-input
+                  ^~ unexpected '=>', ignoring it
+
+p[p a, x: b => value]
+           ^ expected a matching `]`
+                    ^ unexpected ']', expecting end-of-input
+                    ^ unexpected ']', ignoring it
+
diff --git a/test/prism/fixtures/command_method_call_3.txt b/test/prism/fixtures/command_method_call_3.txt
new file mode 100644
index 00000000000000..6de0446aa9be74
--- /dev/null
+++ b/test/prism/fixtures/command_method_call_3.txt
@@ -0,0 +1,19 @@
+foo(bar 1, key => '2')
+
+foo(bar 1, KEY => '2')
+
+foo(bar 1, :key => '2')
+
+foo(bar 1, { baz: :bat } => '2')
+
+foo bar - %i[baz] => '2'
+
+foo(bar {} => '2')
+
+foo(bar baz {} => '2')
+
+foo(bar do end => '2')
+
+foo(1, bar {} => '2')
+
+foo(1, bar do end => '2')

From 5c0c0dd8737c8225f0ebcf0eaf3fb8b71917ee4d Mon Sep 17 00:00:00 2001
From: Kevin Newton <kddnewton@gmail.com>
Date: Thu, 18 Dec 2025 10:10:13 -0500
Subject: [PATCH 04/14] [ruby/prism] Bump to v1.7.0

https://github.com/ruby/prism/commit/21c499d6e4
---
 lib/prism/prism.gemspec                    | 2 +-
 prism/extension.h                          | 2 +-
 prism/templates/lib/prism/serialize.rb.erb | 2 +-
 prism/version.h                            | 4 ++--
 4 files changed, 5 insertions(+), 5 deletions(-)

diff --git a/lib/prism/prism.gemspec b/lib/prism/prism.gemspec
index d9872f88acffd9..2fb5d1d0b308e4 100644
--- a/lib/prism/prism.gemspec
+++ b/lib/prism/prism.gemspec
@@ -2,7 +2,7 @@
 
 Gem::Specification.new do |spec|
   spec.name = "prism"
-  spec.version = "1.6.0"
+  spec.version = "1.7.0"
   spec.authors = ["Shopify"]
   spec.email = ["ruby@shopify.com"]
 
diff --git a/prism/extension.h b/prism/extension.h
index 70017a4ae39ca2..6c3de31adb94d6 100644
--- a/prism/extension.h
+++ b/prism/extension.h
@@ -1,7 +1,7 @@
 #ifndef PRISM_EXT_NODE_H
 #define PRISM_EXT_NODE_H
 
-#define EXPECTED_PRISM_VERSION "1.6.0"
+#define EXPECTED_PRISM_VERSION "1.7.0"
 
 #include <ruby.h>
 #include <ruby/encoding.h>
diff --git a/prism/templates/lib/prism/serialize.rb.erb b/prism/templates/lib/prism/serialize.rb.erb
index 526be67431f0f0..63f97dddd790b1 100644
--- a/prism/templates/lib/prism/serialize.rb.erb
+++ b/prism/templates/lib/prism/serialize.rb.erb
@@ -10,7 +10,7 @@ module Prism
 
     # The minor version of prism that we are expecting to find in the serialized
     # strings.
-    MINOR_VERSION = 6
+    MINOR_VERSION = 7
 
     # The patch version of prism that we are expecting to find in the serialized
     # strings.
diff --git a/prism/version.h b/prism/version.h
index f202b0f4d72c3a..0b64a70dfff5c0 100644
--- a/prism/version.h
+++ b/prism/version.h
@@ -14,7 +14,7 @@
 /**
  * The minor version of the Prism library as an int.
  */
-#define PRISM_VERSION_MINOR 6
+#define PRISM_VERSION_MINOR 7
 
 /**
  * The patch version of the Prism library as an int.
@@ -24,6 +24,6 @@
 /**
  * The version of the Prism library as a constant string.
  */
-#define PRISM_VERSION "1.6.0"
+#define PRISM_VERSION "1.7.0"
 
 #endif

From fec5363ba6fb541bfe4d9c6101f4faf8ffe90f3b Mon Sep 17 00:00:00 2001
From: git <svn-admin@ruby-lang.org>
Date: Fri, 19 Dec 2025 00:59:55 +0000
Subject: [PATCH 05/14] Update default gems list at
 5c0c0dd8737c8225f0ebcf0eaf3fb8 [ci skip]

---
 NEWS.md | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/NEWS.md b/NEWS.md
index 3d1807beb6100a..3379433f2a72ca 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -308,7 +308,7 @@ The following default gems are updated.
 * openssl 4.0.0
 * optparse 0.8.1
 * pp 0.6.3
-* prism 1.6.0
+* prism 1.7.0
 * psych 5.3.1
 * resolv 0.7.0
 * stringio 3.2.0

From 68a900e30b4ca1537d7975c3a619fd94fca7b084 Mon Sep 17 00:00:00 2001
From: Aaron Patterson <tenderlove@ruby-lang.org>
Date: Thu, 18 Dec 2025 17:03:15 -0800
Subject: [PATCH 06/14] add news for pack / unpack directives

---
 NEWS.md | 7 +++++++
 1 file changed, 7 insertions(+)

diff --git a/NEWS.md b/NEWS.md
index 3379433f2a72ca..a5f657fb18f7a3 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -87,6 +87,9 @@ Note: We're only listing outstanding class updates.
     * `Array#rfind` has been added as a more efficient alternative to `array.reverse_each.find` [[Feature #21678]]
     * `Array#find` has been added as a more efficient override of `Enumerable#find` [[Feature #21678]]
 
+    * `Array#pack` accepts a new format `R` and `r` for unpacking unsigned
+      and signed LEB128 encoded integers. [[Feature #21785]]
+
 * Binding
 
     * `Binding#local_variables` does no longer include numbered parameters.
@@ -239,6 +242,9 @@ Note: We're only listing outstanding class updates.
     * `String#strip`, `strip!`, `lstrip`, `lstrip!`, `rstrip`, and `rstrip!`
        are extended to accept `*selectors` arguments. [[Feature #21552]]
 
+    * `String#unpack` accepts a new format `R` and `r` for unpacking unsigned
+      and signed LEB128 encoded integers. [[Feature #21785]]
+
 * Thread
 
     * Introduce support for `Thread#raise(cause:)` argument similar to
@@ -545,3 +551,4 @@ A lot of work has gone into making Ractors more stable, performant, and usable.
 [Feature #21678]: https://bugs.ruby-lang.org/issues/21678
 [Bug #21698]:     https://bugs.ruby-lang.org/issues/21698
 [Feature #21701]: https://bugs.ruby-lang.org/issues/21701
+[Feature #21785]: https://bugs.ruby-lang.org/issues/21785

From 81ad407475149ea47a78875444e0aef5ee4f6635 Mon Sep 17 00:00:00 2001
From: Soutaro Matsumoto <matsumoto@soutaro.com>
Date: Fri, 19 Dec 2025 11:43:58 +0900
Subject: [PATCH 07/14] Fix rbs test failure caused by minitest-6 (#15643)

* Fix rbs test failure caused by minitest6
* Bundle minitest-6.0.0
---
 common.mk         | 2 +-
 gems/bundled_gems | 4 ++--
 2 files changed, 3 insertions(+), 3 deletions(-)

diff --git a/common.mk b/common.mk
index 50abfeab8a4df6..c0d663f68e5658 100644
--- a/common.mk
+++ b/common.mk
@@ -1566,7 +1566,7 @@ yes-install-for-test-bundled-gems: yes-update-default-gemspecs
 	$(XRUBY) -C "$(srcdir)" -r./tool/lib/gem_env.rb bin/gem \
 		install --no-document --conservative \
 		"hoe" "json-schema:5.1.0" "test-unit-rr" "simplecov" "simplecov-html" "simplecov-json" "rspec" "zeitwerk" \
-		"sinatra" "rack" "tilt" "mustermann" "base64" "compact_index" "rack-test" "logger" "kpeg" "tracer"
+		"sinatra" "rack" "tilt" "mustermann" "base64" "compact_index" "rack-test" "logger" "kpeg" "tracer" "minitest-mock"
 
 test-bundled-gems-fetch: yes-test-bundled-gems-fetch
 yes-test-bundled-gems-fetch: clone-bundled-gems-src
diff --git a/gems/bundled_gems b/gems/bundled_gems
index 6717d7e1924180..3a2d410f269d7b 100644
--- a/gems/bundled_gems
+++ b/gems/bundled_gems
@@ -6,7 +6,7 @@
 # - revision: revision in repository-url to test
 #   if `revision` is not given, "v"+`version` or `version` will be used.
 
-minitest            5.27.0  https://github.com/minitest/minitest
+minitest            6.0.0  https://github.com/minitest/minitest
 power_assert        3.0.1   https://github.com/ruby/power_assert
 rake                13.3.1  https://github.com/ruby/rake
 test-unit           3.7.3   https://github.com/test-unit/test-unit
@@ -18,7 +18,7 @@ net-pop             0.1.2   https://github.com/ruby/net-pop
 net-smtp            0.5.1   https://github.com/ruby/net-smtp
 matrix              0.4.3   https://github.com/ruby/matrix
 prime               0.1.4   https://github.com/ruby/prime
-rbs                 3.10.0.pre.2   https://github.com/ruby/rbs
+rbs                 3.10.0.pre.2   https://github.com/ruby/rbs badcb9165b52c1b7ccaa6251e4d5bbd78329c5a7
 typeprof            0.31.0  https://github.com/ruby/typeprof
 debug               1.11.0  https://github.com/ruby/debug
 racc                1.8.1   https://github.com/ruby/racc

From b90d3a6beef7e960dca737efcbff18f8fffa31c0 Mon Sep 17 00:00:00 2001
From: git <svn-admin@ruby-lang.org>
Date: Fri, 19 Dec 2025 02:44:57 +0000
Subject: [PATCH 08/14] Update bundled gems list as of 2025-12-19

---
 NEWS.md           | 6 +++---
 gems/bundled_gems | 4 ++--
 2 files changed, 5 insertions(+), 5 deletions(-)

diff --git a/NEWS.md b/NEWS.md
index a5f657fb18f7a3..b10270c17eae25 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -330,19 +330,19 @@ The following bundled gems are added.
 
 The following bundled gems are updated.
 
-* minitest 5.27.0
+* minitest 6.0.0
 * power_assert 3.0.1
 * rake 13.3.1
 * test-unit 3.7.3
 * rexml 3.4.4
 * net-ftp 0.3.9
-* net-imap 0.6.1
+* net-imap 0.6.2
 * net-smtp 0.5.1
 * matrix 0.4.3
 * prime 0.1.4
 * rbs 3.10.0.pre.2
 * typeprof 0.31.0
-* debug 1.11.0
+* debug 1.11.1
 * base64 0.3.0
 * bigdecimal 4.0.1
 * drb 2.2.3
diff --git a/gems/bundled_gems b/gems/bundled_gems
index 3a2d410f269d7b..a305ca7091d775 100644
--- a/gems/bundled_gems
+++ b/gems/bundled_gems
@@ -13,14 +13,14 @@ test-unit           3.7.3   https://github.com/test-unit/test-unit
 rexml               3.4.4   https://github.com/ruby/rexml
 rss                 0.3.1   https://github.com/ruby/rss
 net-ftp             0.3.9   https://github.com/ruby/net-ftp
-net-imap            0.6.1   https://github.com/ruby/net-imap
+net-imap            0.6.2   https://github.com/ruby/net-imap
 net-pop             0.1.2   https://github.com/ruby/net-pop
 net-smtp            0.5.1   https://github.com/ruby/net-smtp
 matrix              0.4.3   https://github.com/ruby/matrix
 prime               0.1.4   https://github.com/ruby/prime
 rbs                 3.10.0.pre.2   https://github.com/ruby/rbs badcb9165b52c1b7ccaa6251e4d5bbd78329c5a7
 typeprof            0.31.0  https://github.com/ruby/typeprof
-debug               1.11.0  https://github.com/ruby/debug
+debug               1.11.1  https://github.com/ruby/debug
 racc                1.8.1   https://github.com/ruby/racc
 mutex_m             0.3.0   https://github.com/ruby/mutex_m
 getoptlong          0.2.1   https://github.com/ruby/getoptlong

From 305f04210545d6801b2a4821a91858f0aed84f01 Mon Sep 17 00:00:00 2001
From: Yusuke Endoh <mame@ruby-lang.org>
Date: Fri, 19 Dec 2025 10:26:59 +0900
Subject: [PATCH 09/14] NEWS.md: Sort items in alphabetical order

---
 NEWS.md | 121 ++++++++++++++++++++++++++++----------------------------
 1 file changed, 60 insertions(+), 61 deletions(-)

diff --git a/NEWS.md b/NEWS.md
index b10270c17eae25..af3e78ddaaba3f 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -33,6 +33,24 @@ Note that each entry is kept to a minimum, see links for details.
 
 Note: We're only listing outstanding class updates.
 
+* Array
+
+    * `Array#rfind` has been added as a more efficient alternative to `array.reverse_each.find` [[Feature #21678]]
+    * `Array#find` has been added as a more efficient override of `Enumerable#find` [[Feature #21678]]
+    * `Array#pack` accepts a new format `R` and `r` for unpacking unsigned
+      and signed LEB128 encoded integers. [[Feature #21785]]
+
+* Binding
+
+    * `Binding#local_variables` does no longer include numbered parameters.
+      Also, `Binding#local_variable_get`, `Binding#local_variable_set`, and
+      `Binding#local_variable_defined?` reject to handle numbered parameters.
+      [[Bug #21049]]
+
+    * `Binding#implicit_parameters`, `Binding#implicit_parameter_get`, and
+      `Binding#implicit_parameter_defined?` have been added to access
+      numbered parameters and "it" parameter. [[Bug #21049]]
+
 * Enumerator
 
     * `Enumerator.produce` now accepts an optional `size` keyword argument
@@ -57,50 +75,6 @@ Note: We're only listing outstanding class updates.
 
       [[Feature #21701]]
 
-* Kernel
-
-    * `Kernel#inspect` now checks for the existence of a `#instance_variables_to_inspect` method,
-      allowing control over which instance variables are displayed in the `#inspect` string:
-
-        ```ruby
-        class DatabaseConfig
-          def initialize(host, user, password)
-            @host = host
-            @user = user
-            @password = password
-          end
-
-          private def instance_variables_to_inspect = [:@host, :@user]
-        end
-
-        conf = DatabaseConfig.new("localhost", "root", "hunter2")
-        conf.inspect #=> #<DatabaseConfig:0x0000000104def350 @host="localhost", @user="root">
-        ```
-
-        [[Feature #21219]]
-
-    * A deprecated behavior, process creation by `Kernel#open` with a
-      leading `|`, was removed.  [[Feature #19630]]
-
-* Array
-
-    * `Array#rfind` has been added as a more efficient alternative to `array.reverse_each.find` [[Feature #21678]]
-    * `Array#find` has been added as a more efficient override of `Enumerable#find` [[Feature #21678]]
-
-    * `Array#pack` accepts a new format `R` and `r` for unpacking unsigned
-      and signed LEB128 encoded integers. [[Feature #21785]]
-
-* Binding
-
-    * `Binding#local_variables` does no longer include numbered parameters.
-      Also, `Binding#local_variable_get`, `Binding#local_variable_set`, and
-      `Binding#local_variable_defined?` reject to handle numbered parameters.
-      [[Bug #21049]]
-
-    * `Binding#implicit_parameters`, `Binding#implicit_parameter_get`, and
-      `Binding#implicit_parameter_defined?` have been added to access
-      numbered parameters and "it" parameter. [[Bug #21049]]
-
 * ErrorHighlight
 
     * When an ArgumentError is raised, it now displays code snippets for
@@ -119,6 +93,18 @@ Note: We're only listing outstanding class updates.
               from test.rb:3:in '<main>'
       ```
 
+* Fiber
+
+    * Introduce support for `Fiber#raise(cause:)` argument similar to
+      `Kernel#raise`. [[Feature #21360]]
+
+* Fiber::Scheduler
+
+    * Introduce `Fiber::Scheduler#fiber_interrupt` to interrupt a fiber with a
+      given exception. The initial use case is to interrupt a fiber that is
+      waiting on a blocking IO operation when the IO operation is closed.
+      [[Feature #21166]]
+
 * File
 
     * `File::Stat#birthtime` is now available on Linux via the statx
@@ -133,10 +119,40 @@ Note: We're only listing outstanding class updates.
     * A deprecated behavior, process creation by `IO` class methods
       with a leading `|`, was removed.  [[Feature #19630]]
 
+* Kernel
+
+    * `Kernel#inspect` now checks for the existence of a `#instance_variables_to_inspect` method,
+      allowing control over which instance variables are displayed in the `#inspect` string:
+
+        ```ruby
+        class DatabaseConfig
+          def initialize(host, user, password)
+            @host = host
+            @user = user
+            @password = password
+          end
+
+          private def instance_variables_to_inspect = [:@host, :@user]
+        end
+
+        conf = DatabaseConfig.new("localhost", "root", "hunter2")
+        conf.inspect #=> #<DatabaseConfig:0x0000000104def350 @host="localhost", @user="root">
+        ```
+
+        [[Feature #21219]]
+
+    * A deprecated behavior, process creation by `Kernel#open` with a
+      leading `|`, was removed.  [[Feature #19630]]
+
 * Math
 
     * `Math.log1p` and `Math.expm1` are added. [[Feature #21527]]
 
+* Pathname
+
+    * Pathname has been promoted from a default gem to a core class of Ruby.
+      [[Feature #17473]]
+
 * Proc
 
     * `Proc#parameters` now shows anonymous optional parameters as `[:opt]`
@@ -250,23 +266,6 @@ Note: We're only listing outstanding class updates.
     * Introduce support for `Thread#raise(cause:)` argument similar to
       `Kernel#raise`. [[Feature #21360]]
 
-* Fiber
-
-    * Introduce support for `Fiber#raise(cause:)` argument similar to
-      `Kernel#raise`. [[Feature #21360]]
-
-* Fiber::Scheduler
-
-    * Introduce `Fiber::Scheduler#fiber_interrupt` to interrupt a fiber with a
-      given exception. The initial use case is to interrupt a fiber that is
-      waiting on a blocking IO operation when the IO operation is closed.
-      [[Feature #21166]]
-
-* Pathname
-
-    * Pathname has been promoted from a default gem to a core class of Ruby.
-      [[Feature #17473]]
-
 ## Stdlib updates
 
 The following bundled gems are promoted from default gems.

From 42d66b894cdfa356ed67af3000f79f7b2e9185fe Mon Sep 17 00:00:00 2001
From: Misaki Shioi <31817032+shioimm@users.noreply.github.com>
Date: Fri, 19 Dec 2025 12:12:12 +0900
Subject: [PATCH 10/14] Fix: Do not check open_timeout twice (#15626)

---
 ext/socket/ipsocket.c | 4 ++--
 1 file changed, 2 insertions(+), 2 deletions(-)

diff --git a/ext/socket/ipsocket.c b/ext/socket/ipsocket.c
index 88225f76e5c882..c9fcfb64fb4eb0 100644
--- a/ext/socket/ipsocket.c
+++ b/ext/socket/ipsocket.c
@@ -633,7 +633,7 @@ init_fast_fallback_inetsock_internal(VALUE v)
         unsigned int t;
         if (!NIL_P(open_timeout)) {
             t = rsock_value_timeout_to_msec(open_timeout);
-        } else if (!NIL_P(open_timeout)) {
+        } else if (!NIL_P(resolv_timeout)) {
             t = rsock_value_timeout_to_msec(resolv_timeout);
         } else {
             t = 0;
@@ -1340,7 +1340,7 @@ rsock_init_inetsock(
                 unsigned int t;
                 if (!NIL_P(open_timeout)) {
                     t = rsock_value_timeout_to_msec(open_timeout);
-                } else if (!NIL_P(open_timeout)) {
+                } else if (!NIL_P(resolv_timeout)) {
                     t = rsock_value_timeout_to_msec(resolv_timeout);
                 } else {
                     t = 0;

From bfba65d8c1fcdc75ea3fc0f78d8bc7514e7afabd Mon Sep 17 00:00:00 2001
From: Nobuyoshi Nakada <nobu@ruby-lang.org>
Date: Fri, 19 Dec 2025 09:26:23 +0900
Subject: [PATCH 11/14] Extract `Test::JobServer` module

A placeholder to handle GNU make jobserver option.
spec/default.mspec didn't handle the jobserver using a FIFO.
---
 bootstraptest/runner.rb    | 31 ++-----------------------
 spec/default.mspec         | 33 ++++----------------------
 tool/lib/test/jobserver.rb | 47 ++++++++++++++++++++++++++++++++++++++
 tool/lib/test/unit.rb      | 24 +++----------------
 4 files changed, 57 insertions(+), 78 deletions(-)
 create mode 100644 tool/lib/test/jobserver.rb

diff --git a/bootstraptest/runner.rb b/bootstraptest/runner.rb
index 8988ac20ce41f6..04de0c93b90cb0 100755
--- a/bootstraptest/runner.rb
+++ b/bootstraptest/runner.rb
@@ -16,6 +16,7 @@
   $:.unshift File.join(File.dirname(__FILE__), '../lib')
   retry
 end
+require_relative '../tool/lib/test/jobserver'
 
 if !Dir.respond_to?(:mktmpdir)
   # copied from lib/tmpdir.rb
@@ -110,35 +111,7 @@ def putc(c)
 
   def wn=(wn)
     unless wn == 1
-      if /(?:\A|\s)--jobserver-(?:auth|fds)=(?:(\d+),(\d+)|fifo:((?:\\.|\S)+))/ =~ ENV.delete("MAKEFLAGS")
-        begin
-          if fifo = $3
-            fifo.gsub!(/\\(?=.)/, '')
-            r = File.open(fifo, IO::RDONLY|IO::NONBLOCK|IO::BINARY)
-            w = File.open(fifo, IO::WRONLY|IO::NONBLOCK|IO::BINARY)
-          else
-            r = IO.for_fd($1.to_i(10), "rb", autoclose: false)
-            w = IO.for_fd($2.to_i(10), "wb", autoclose: false)
-          end
-        rescue
-          r.close if r
-        else
-          r.close_on_exec = true
-          w.close_on_exec = true
-          tokens = r.read_nonblock(wn > 0 ? wn : 1024, exception: false)
-          r.close
-          if String === tokens
-            tokens.freeze
-            auth = w
-            w = nil
-            at_exit {auth << tokens; auth.close}
-            wn = tokens.size + 1
-          else
-            w.close
-            wn = 1
-          end
-        end
-      end
+      wn = Test::JobServer.max_jobs(wn > 0 ? wn : 1024, ENV.delete("MAKEFLAGS")) || wn
       if wn <= 0
         require 'etc'
         wn = [Etc.nprocessors / 2, 1].max
diff --git a/spec/default.mspec b/spec/default.mspec
index 058835cd10d91c..d756dc31ffd566 100644
--- a/spec/default.mspec
+++ b/spec/default.mspec
@@ -9,6 +9,7 @@ ENV["CHECK_CONSTANT_LEAKS"] ||= "true"
 
 require "./rbconfig" unless defined?(RbConfig)
 require_relative "../tool/test-coverage" if ENV.key?("COVERAGE")
+require_relative "../tool/lib/test/jobserver"
 load File.dirname(__FILE__) + '/ruby/default.mspec'
 OBJDIR = File.expand_path("spec/ruby/optional/capi/ext") unless defined?(OBJDIR)
 class MSpecScript
@@ -50,34 +51,10 @@ end
 
 module MSpecScript::JobServer
   def cores(max = 1)
-    if max > 1 and /(?:\A|\s)--jobserver-(?:auth|fds)=(\d+),(\d+)/ =~ ENV["MAKEFLAGS"]
-      cores = 1
-      begin
-        r = IO.for_fd($1.to_i(10), "rb", autoclose: false)
-        w = IO.for_fd($2.to_i(10), "wb", autoclose: false)
-        jobtokens = r.read_nonblock(max - 1)
-        cores = jobtokens.size
-        if cores > 0
-          cores += 1
-          jobserver = w
-          w = nil
-          at_exit {
-            jobserver.print(jobtokens)
-            jobserver.close
-          }
-          MSpecScript::JobServer.module_eval do
-            remove_method :cores
-            define_method(:cores) do
-              cores
-            end
-          end
-          return cores
-        end
-      rescue Errno::EBADF
-      ensure
-        r&.close
-        w&.close
-      end
+    MSpecScript::JobServer.remove_method :cores
+    if cores = Test::JobServer.max_jobs(max)
+      MSpecScript::JobServer.define_method(:cores) { cores }
+      return cores
     end
     super
   end
diff --git a/tool/lib/test/jobserver.rb b/tool/lib/test/jobserver.rb
new file mode 100644
index 00000000000000..7b889163b02aa2
--- /dev/null
+++ b/tool/lib/test/jobserver.rb
@@ -0,0 +1,47 @@
+module Test
+  module JobServer
+  end
+end
+
+class << Test::JobServer
+  def connect(makeflags = ENV["MAKEFLAGS"])
+    return unless /(?:\A|\s)--jobserver-(?:auth|fds)=(?:(\d+),(\d+)|fifo:((?:\\.|\S)+))/ =~ makeflags
+    begin
+      if fifo = $3
+        fifo.gsub!(/\\(?=.)/, '')
+        r = File.open(fifo, IO::RDONLY|IO::NONBLOCK|IO::BINARY)
+        w = File.open(fifo, IO::WRONLY|IO::NONBLOCK|IO::BINARY)
+      else
+        r = IO.for_fd($1.to_i(10), "rb", autoclose: false)
+        w = IO.for_fd($2.to_i(10), "wb", autoclose: false)
+      end
+    rescue
+      r&.close
+      nil
+    else
+      return r, w
+    end
+  end
+
+  def acquire_possible(r, w, max)
+    return unless tokens = r.read_nonblock(max - 1, exception: false)
+    if (jobs = tokens.size) > 0
+      jobserver, w = w, nil
+      at_exit do
+        jobserver.print(tokens)
+        jobserver.close
+      end
+    end
+    return jobs + 1
+  rescue Errno::EBADF
+  ensure
+    r&.close
+    w&.close
+  end
+
+  def max_jobs(max = 2, makeflags = ENV["MAKEFLAGS"])
+    if max > 1 and (r, w = connect(makeflags))
+      acquire_possible(r, w, max)
+    end
+  end
+end
diff --git a/tool/lib/test/unit.rb b/tool/lib/test/unit.rb
index 7d43e825e179eb..2663b7b76a10bf 100644
--- a/tool/lib/test/unit.rb
+++ b/tool/lib/test/unit.rb
@@ -19,6 +19,7 @@ def warn(message, category: nil, **kwargs)
 require_relative '../colorize'
 require_relative '../leakchecker'
 require_relative '../test/unit/testcase'
+require_relative '../test/jobserver'
 require 'optparse'
 
 # See Test::Unit
@@ -262,27 +263,8 @@ def process_args(args = [])
 
       def non_options(files, options)
         @jobserver = nil
-        makeflags = ENV.delete("MAKEFLAGS")
-        if !options[:parallel] and
-          /(?:\A|\s)--jobserver-(?:auth|fds)=(?:(\d+),(\d+)|fifo:((?:\\.|\S)+))/ =~ makeflags
-          begin
-            if fifo = $3
-              fifo.gsub!(/\\(?=.)/, '')
-              r = File.open(fifo, IO::RDONLY|IO::NONBLOCK|IO::BINARY)
-              w = File.open(fifo, IO::WRONLY|IO::NONBLOCK|IO::BINARY)
-            else
-              r = IO.for_fd($1.to_i(10), "rb", autoclose: false)
-              w = IO.for_fd($2.to_i(10), "wb", autoclose: false)
-            end
-          rescue
-            r.close if r
-            nil
-          else
-            r.close_on_exec = true
-            w.close_on_exec = true
-            @jobserver = [r, w]
-            options[:parallel] ||= 256 # number of tokens to acquire first
-          end
+        if !options[:parallel] and @jobserver = Test::JobServer.connect(ENV.delete("MAKEFLAGS"))
+          options[:parallel] ||= 256 # number of tokens to acquire first
         end
         @worker_timeout = EnvUtil.apply_timeout_scale(options[:worker_timeout] || 1200)
         super

From 6f6ea70dcea1bbcb00774c1da58735a78c8924c2 Mon Sep 17 00:00:00 2001
From: Nobuyoshi Nakada <nobu@ruby-lang.org>
Date: Fri, 19 Dec 2025 09:47:22 +0900
Subject: [PATCH 12/14] Just passing FDs does not need to create IO objects

---
 spec/ruby/optional/capi/spec_helper.rb | 10 +++-------
 1 file changed, 3 insertions(+), 7 deletions(-)

diff --git a/spec/ruby/optional/capi/spec_helper.rb b/spec/ruby/optional/capi/spec_helper.rb
index 1076b206ecbdb6..e7abf46e6ccf65 100644
--- a/spec/ruby/optional/capi/spec_helper.rb
+++ b/spec/ruby/optional/capi/spec_helper.rb
@@ -122,13 +122,9 @@ def setup_make
 
   opts = {}
   if /(?:\A|\s)--jobserver-(?:auth|fds)=(\d+),(\d+)/ =~ make_flags
-    begin
-      r = IO.for_fd($1.to_i(10), "rb", autoclose: false)
-      w = IO.for_fd($2.to_i(10), "wb", autoclose: false)
-    rescue Errno::EBADF
-    else
-      opts[r] = r
-      opts[w] = w
+    [$1, $2].each do |fd|
+      fd = fd.to_i(10)
+      opts[fd] = fd
     end
   end
 

From f81c62be3df7b29c4c3b6adaa16599b38d0c0c46 Mon Sep 17 00:00:00 2001
From: yui-knk <spiketeika@gmail.com>
Date: Fri, 19 Dec 2025 11:46:58 +0900
Subject: [PATCH 13/14] Terminate `args_tail_basic` rule with a semicolon

Semicolon is optional however it clarifies the end of the rule.
---
 parse.y | 1 +
 1 file changed, 1 insertion(+)

diff --git a/parse.y b/parse.y
index 4754435fab0d21..067f45e6d6044a 100644
--- a/parse.y
+++ b/parse.y
@@ -2943,6 +2943,7 @@ rb_parser_ary_free(rb_parser_t *p, rb_parser_ary_t *ary)
                         $$ = new_args_tail(p, 0, 0, $1, &@1);
                     /*% ripper: [Qnil, Qnil, $:1] %*/
                     }
+                ;
 
 %rule def_endless_method(bodystmt) <node>
                 : defn_head[head] f_opt_paren_args[args] '=' bodystmt

From 47244b0f306161f175b21f74d801882e950e18be Mon Sep 17 00:00:00 2001
From: Misaki Shioi <31817032+shioimm@users.noreply.github.com>
Date: Fri, 19 Dec 2025 15:44:35 +0900
Subject: [PATCH 14/14] Fix: Specifying 0 should cause an immediate timeout
 (#15641)

This change fixes a bug in which specifying 0 for timeout-related options (such as the `timeout` option of `Addrinfo.getaddrinfo`) incorrectly results in an infinite wait.

(This change overwrites https://github.com/ruby/ruby/pull/15626 .)
---
 ext/socket/ipsocket.c      | 27 +++++----------------------
 ext/socket/raddrinfo.c     | 29 ++++++++++++++++-------------
 ext/socket/rubysocket.h    |  5 ++---
 ext/socket/socket.c        |  8 ++++----
 ext/socket/tcpsocket.c     |  2 +-
 ext/socket/udpsocket.c     |  6 +++---
 test/socket/test_socket.rb |  2 +-
 7 files changed, 32 insertions(+), 47 deletions(-)

diff --git a/ext/socket/ipsocket.c b/ext/socket/ipsocket.c
index c9fcfb64fb4eb0..e952b7871b3f6f 100644
--- a/ext/socket/ipsocket.c
+++ b/ext/socket/ipsocket.c
@@ -83,15 +83,13 @@ init_inetsock_internal(VALUE v)
     VALUE open_timeout = arg->open_timeout;
     VALUE timeout;
     VALUE starts_at;
-    unsigned int timeout_msec;
 
     timeout = NIL_P(open_timeout) ? resolv_timeout : open_timeout;
-    timeout_msec = NIL_P(timeout) ? 0 : rsock_value_timeout_to_msec(timeout);
     starts_at = current_clocktime();
 
     arg->remote.res = rsock_addrinfo(arg->remote.host, arg->remote.serv,
                                      family, SOCK_STREAM,
-                                     (type == INET_SERVER) ? AI_PASSIVE : 0, timeout_msec);
+                                     (type == INET_SERVER) ? AI_PASSIVE : 0, timeout);
 
     /*
      * Maybe also accept a local address
@@ -99,7 +97,7 @@ init_inetsock_internal(VALUE v)
 
     if (type != INET_SERVER && (!NIL_P(arg->local.host) || !NIL_P(arg->local.serv))) {
         arg->local.res = rsock_addrinfo(arg->local.host, arg->local.serv,
-                                        family, SOCK_STREAM, 0, 0);
+                                        family, SOCK_STREAM, 0, timeout);
     }
 
     VALUE io = Qnil;
@@ -630,14 +628,7 @@ init_fast_fallback_inetsock_internal(VALUE v)
         arg->getaddrinfo_shared = NULL;
 
         int family = arg->families[0];
-        unsigned int t;
-        if (!NIL_P(open_timeout)) {
-            t = rsock_value_timeout_to_msec(open_timeout);
-        } else if (!NIL_P(resolv_timeout)) {
-            t = rsock_value_timeout_to_msec(resolv_timeout);
-        } else {
-            t = 0;
-        }
+        VALUE t = NIL_P(open_timeout) ? resolv_timeout : open_timeout;
 
         arg->remote.res = rsock_addrinfo(
             arg->remote.host,
@@ -1337,15 +1328,7 @@ rsock_init_inetsock(
              * Maybe also accept a local address
              */
             if (!NIL_P(local_host) || !NIL_P(local_serv)) {
-                unsigned int t;
-                if (!NIL_P(open_timeout)) {
-                    t = rsock_value_timeout_to_msec(open_timeout);
-                } else if (!NIL_P(resolv_timeout)) {
-                    t = rsock_value_timeout_to_msec(resolv_timeout);
-                } else {
-                    t = 0;
-                }
-
+                VALUE t = NIL_P(open_timeout) ? resolv_timeout : open_timeout;
                 local_res = rsock_addrinfo(
                     local_host,
                     local_serv,
@@ -1609,7 +1592,7 @@ static VALUE
 ip_s_getaddress(VALUE obj, VALUE host)
 {
     union_sockaddr addr;
-    struct rb_addrinfo *res = rsock_addrinfo(host, Qnil, AF_UNSPEC, SOCK_STREAM, 0, 0);
+    struct rb_addrinfo *res = rsock_addrinfo(host, Qnil, AF_UNSPEC, SOCK_STREAM, 0, Qnil);
     socklen_t len = res->ai->ai_addrlen;
 
     /* just take the first one */
diff --git a/ext/socket/raddrinfo.c b/ext/socket/raddrinfo.c
index 3dcbe7717a0ca2..6cdf5c6abc40e7 100644
--- a/ext/socket/raddrinfo.c
+++ b/ext/socket/raddrinfo.c
@@ -293,7 +293,7 @@ rb_freeaddrinfo(struct rb_addrinfo *ai)
     xfree(ai);
 }
 
-unsigned int
+static int
 rsock_value_timeout_to_msec(VALUE timeout)
 {
     double seconds = NUM2DBL(timeout);
@@ -308,7 +308,7 @@ rsock_value_timeout_to_msec(VALUE timeout)
 #if GETADDRINFO_IMPL == 0
 
 static int
-rb_getaddrinfo(const char *hostp, const char *portp, const struct addrinfo *hints, struct addrinfo **ai, unsigned int _timeout)
+rb_getaddrinfo(const char *hostp, const char *portp, const struct addrinfo *hints, struct addrinfo **ai, int _timeout)
 {
     return getaddrinfo(hostp, portp, hints, ai);
 }
@@ -346,7 +346,7 @@ fork_safe_getaddrinfo(void *arg)
 }
 
 static int
-rb_getaddrinfo(const char *hostp, const char *portp, const struct addrinfo *hints, struct addrinfo **ai, unsigned int _timeout)
+rb_getaddrinfo(const char *hostp, const char *portp, const struct addrinfo *hints, struct addrinfo **ai, int _timeout)
 {
     struct getaddrinfo_arg arg;
     MEMZERO(&arg, struct getaddrinfo_arg, 1);
@@ -367,11 +367,11 @@ struct getaddrinfo_arg
     int err, gai_errno, refcount, done, cancelled, timedout;
     rb_nativethread_lock_t lock;
     rb_nativethread_cond_t cond;
-    unsigned int timeout;
+    int timeout;
 };
 
 static struct getaddrinfo_arg *
-allocate_getaddrinfo_arg(const char *hostp, const char *portp, const struct addrinfo *hints, unsigned int timeout)
+allocate_getaddrinfo_arg(const char *hostp, const char *portp, const struct addrinfo *hints, int timeout)
 {
     size_t hostp_offset = sizeof(struct getaddrinfo_arg);
     size_t portp_offset = hostp_offset + (hostp ? strlen(hostp) + 1 : 0);
@@ -465,8 +465,11 @@ wait_getaddrinfo(void *ptr)
     struct getaddrinfo_arg *arg = (struct getaddrinfo_arg *)ptr;
     rb_nativethread_lock_lock(&arg->lock);
     while (!arg->done && !arg->cancelled) {
-        unsigned long msec = arg->timeout;
-        if (msec > 0) {
+        long msec = arg->timeout;
+        if (msec == 0) {
+            arg->cancelled = 1;
+            arg->timedout = 1;
+        } else if (msec > 0) {
             rb_native_cond_timedwait(&arg->cond, &arg->lock, msec);
             if (!arg->done) {
                 arg->cancelled = 1;
@@ -549,7 +552,7 @@ fork_safe_do_getaddrinfo(void *ptr)
 }
 
 static int
-rb_getaddrinfo(const char *hostp, const char *portp, const struct addrinfo *hints, struct addrinfo **ai, unsigned int timeout)
+rb_getaddrinfo(const char *hostp, const char *portp, const struct addrinfo *hints, struct addrinfo **ai, int timeout)
 {
     int retry;
     struct getaddrinfo_arg *arg;
@@ -1021,7 +1024,7 @@ rb_scheduler_getaddrinfo(VALUE scheduler, VALUE host, const char *service,
 }
 
 struct rb_addrinfo*
-rsock_getaddrinfo(VALUE host, VALUE port, struct addrinfo *hints, int socktype_hack, unsigned int timeout)
+rsock_getaddrinfo(VALUE host, VALUE port, struct addrinfo *hints, int socktype_hack, VALUE timeout)
 {
     struct rb_addrinfo* res = NULL;
     struct addrinfo *ai;
@@ -1056,7 +1059,8 @@ rsock_getaddrinfo(VALUE host, VALUE port, struct addrinfo *hints, int socktype_h
         }
 
         if (!resolved) {
-            error = rb_getaddrinfo(hostp, portp, hints, &ai, timeout);
+            int t = NIL_P(timeout) ? -1 : rsock_value_timeout_to_msec(timeout);
+            error = rb_getaddrinfo(hostp, portp, hints, &ai, t);
             if (error == 0) {
                 res = (struct rb_addrinfo *)xmalloc(sizeof(struct rb_addrinfo));
                 res->allocated_by_malloc = 0;
@@ -1089,7 +1093,7 @@ rsock_fd_family(int fd)
 }
 
 struct rb_addrinfo*
-rsock_addrinfo(VALUE host, VALUE port, int family, int socktype, int flags, unsigned int timeout)
+rsock_addrinfo(VALUE host, VALUE port, int family, int socktype, int flags, VALUE timeout)
 {
     struct addrinfo hints;
 
@@ -1380,8 +1384,7 @@ call_getaddrinfo(VALUE node, VALUE service,
         hints.ai_flags = NUM2INT(flags);
     }
 
-    unsigned int t = NIL_P(timeout) ? 0 : rsock_value_timeout_to_msec(timeout);
-    res = rsock_getaddrinfo(node, service, &hints, socktype_hack, t);
+    res = rsock_getaddrinfo(node, service, &hints, socktype_hack, timeout);
 
     if (res == NULL)
         rb_raise(rb_eSocket, "host not found");
diff --git a/ext/socket/rubysocket.h b/ext/socket/rubysocket.h
index 638b7ede6ec72e..2ec3ab335aef86 100644
--- a/ext/socket/rubysocket.h
+++ b/ext/socket/rubysocket.h
@@ -327,8 +327,8 @@ void rb_freeaddrinfo(struct rb_addrinfo *ai);
 VALUE rsock_freeaddrinfo(VALUE arg);
 int rb_getnameinfo(const struct sockaddr *sa, socklen_t salen, char *host, size_t hostlen, char *serv, size_t servlen, int flags);
 int rsock_fd_family(int fd);
-struct rb_addrinfo *rsock_addrinfo(VALUE host, VALUE port, int family, int socktype, int flags, unsigned int timeout);
-struct rb_addrinfo *rsock_getaddrinfo(VALUE host, VALUE port, struct addrinfo *hints, int socktype_hack, unsigned int timeout);
+struct rb_addrinfo *rsock_addrinfo(VALUE host, VALUE port, int family, int socktype, int flags, VALUE timeout);
+struct rb_addrinfo *rsock_getaddrinfo(VALUE host, VALUE port, struct addrinfo *hints, int socktype_hack, VALUE timeout);
 
 VALUE rsock_fd_socket_addrinfo(int fd, struct sockaddr *addr, socklen_t len);
 VALUE rsock_io_socket_addrinfo(VALUE io, struct sockaddr *addr, socklen_t len);
@@ -453,7 +453,6 @@ void free_fast_fallback_getaddrinfo_shared(struct fast_fallback_getaddrinfo_shar
 #  endif
 #endif
 
-unsigned int rsock_value_timeout_to_msec(VALUE);
 NORETURN(void rsock_raise_user_specified_timeout(struct addrinfo *ai, VALUE host, VALUE port));
 
 void rsock_init_basicsocket(void);
diff --git a/ext/socket/socket.c b/ext/socket/socket.c
index 26bf0bae8c046d..a8e5ae81190c21 100644
--- a/ext/socket/socket.c
+++ b/ext/socket/socket.c
@@ -965,7 +965,7 @@ sock_s_gethostbyname(VALUE obj, VALUE host)
 {
     rb_warn("Socket.gethostbyname is deprecated; use Addrinfo.getaddrinfo instead.");
     struct rb_addrinfo *res =
-        rsock_addrinfo(host, Qnil, AF_UNSPEC, SOCK_STREAM, AI_CANONNAME, 0);
+        rsock_addrinfo(host, Qnil, AF_UNSPEC, SOCK_STREAM, AI_CANONNAME, Qnil);
     return rsock_make_hostent(host, res, sock_sockaddr);
 }
 
@@ -1183,7 +1183,7 @@ sock_s_getaddrinfo(int argc, VALUE *argv, VALUE _)
         norevlookup = rsock_do_not_reverse_lookup;
     }
 
-    res = rsock_getaddrinfo(host, port, &hints, 0, 0);
+    res = rsock_getaddrinfo(host, port, &hints, 0, Qnil);
 
     ret = make_addrinfo(res, norevlookup);
     rb_freeaddrinfo(res);
@@ -1279,7 +1279,7 @@ sock_s_getnameinfo(int argc, VALUE *argv, VALUE _)
         hints.ai_socktype = (fl & NI_DGRAM) ? SOCK_DGRAM : SOCK_STREAM;
         /* af */
         hints.ai_family = NIL_P(af) ? PF_UNSPEC : rsock_family_arg(af);
-        res = rsock_getaddrinfo(host, port, &hints, 0, 0);
+        res = rsock_getaddrinfo(host, port, &hints, 0, Qnil);
         sap = res->ai->ai_addr;
         salen = res->ai->ai_addrlen;
     }
@@ -1335,7 +1335,7 @@ sock_s_getnameinfo(int argc, VALUE *argv, VALUE _)
 static VALUE
 sock_s_pack_sockaddr_in(VALUE self, VALUE port, VALUE host)
 {
-    struct rb_addrinfo *res = rsock_addrinfo(host, port, AF_UNSPEC, 0, 0, 0);
+    struct rb_addrinfo *res = rsock_addrinfo(host, port, AF_UNSPEC, 0, 0, Qnil);
     VALUE addr = rb_str_new((char*)res->ai->ai_addr, res->ai->ai_addrlen);
 
     rb_freeaddrinfo(res);
diff --git a/ext/socket/tcpsocket.c b/ext/socket/tcpsocket.c
index 300a426eda8471..7ce536e0af9ca3 100644
--- a/ext/socket/tcpsocket.c
+++ b/ext/socket/tcpsocket.c
@@ -113,7 +113,7 @@ tcp_s_gethostbyname(VALUE obj, VALUE host)
 {
     rb_warn("TCPSocket.gethostbyname is deprecated; use Addrinfo.getaddrinfo instead.");
     struct rb_addrinfo *res =
-        rsock_addrinfo(host, Qnil, AF_UNSPEC, SOCK_STREAM, AI_CANONNAME, 0);
+        rsock_addrinfo(host, Qnil, AF_UNSPEC, SOCK_STREAM, AI_CANONNAME, Qnil);
     return rsock_make_hostent(host, res, tcp_sockaddr);
 }
 
diff --git a/ext/socket/udpsocket.c b/ext/socket/udpsocket.c
index 5538f24523fc09..b2bc92553886aa 100644
--- a/ext/socket/udpsocket.c
+++ b/ext/socket/udpsocket.c
@@ -84,7 +84,7 @@ udp_connect(VALUE self, VALUE host, VALUE port)
 {
     struct udp_arg arg = {.io = self};
 
-    arg.res = rsock_addrinfo(host, port, rsock_fd_family(rb_io_descriptor(self)), SOCK_DGRAM, 0, 0);
+    arg.res = rsock_addrinfo(host, port, rsock_fd_family(rb_io_descriptor(self)), SOCK_DGRAM, 0, Qnil);
 
     int result = (int)rb_ensure(udp_connect_internal, (VALUE)&arg, rsock_freeaddrinfo, (VALUE)arg.res);
     if (!result) {
@@ -129,7 +129,7 @@ udp_bind(VALUE self, VALUE host, VALUE port)
 {
     struct udp_arg arg = {.io = self};
 
-    arg.res = rsock_addrinfo(host, port, rsock_fd_family(rb_io_descriptor(self)), SOCK_DGRAM, 0, 0);
+    arg.res = rsock_addrinfo(host, port, rsock_fd_family(rb_io_descriptor(self)), SOCK_DGRAM, 0, Qnil);
 
     VALUE result = rb_ensure(udp_bind_internal, (VALUE)&arg, rsock_freeaddrinfo, (VALUE)arg.res);
     if (!result) {
@@ -212,7 +212,7 @@ udp_send(int argc, VALUE *argv, VALUE sock)
     GetOpenFile(sock, arg.fptr);
     arg.sarg.fd = arg.fptr->fd;
     arg.sarg.flags = NUM2INT(flags);
-    arg.res = rsock_addrinfo(host, port, rsock_fd_family(arg.fptr->fd), SOCK_DGRAM, 0, 0);
+    arg.res = rsock_addrinfo(host, port, rsock_fd_family(arg.fptr->fd), SOCK_DGRAM, 0, Qnil);
     ret = rb_ensure(udp_send_internal, (VALUE)&arg,
                     rsock_freeaddrinfo, (VALUE)arg.res);
     if (!ret) rsock_sys_fail_host_port("sendto(2)", host, port);
diff --git a/test/socket/test_socket.rb b/test/socket/test_socket.rb
index 686114f05c1418..c42527f3703173 100644
--- a/test/socket/test_socket.rb
+++ b/test/socket/test_socket.rb
@@ -1011,7 +1011,7 @@ def test_tcp_socket_all_hostname_resolution_failed
       Addrinfo.define_singleton_method(:getaddrinfo) do |_, _, family, *_|
         case family
         when Socket::AF_INET6 then raise SocketError
-        when Socket::AF_INET then sleep(0.001); raise SocketError, "Last hostname resolution error"
+        when Socket::AF_INET then sleep(0.01); raise SocketError, "Last hostname resolution error"
         end
       end