https://git.ruby-lang.org/ruby.git/commit/?id=43239b23b4

From 43239b23b48a6c3fde6bdc4b9cc568bedac161b2 Mon Sep 17 00:00:00 2001
From: Nobuyoshi Nakada <nobu@r...>
Date: Mon, 8 Aug 2022 23:26:21 +0900
Subject: [Bug #18946] New tests for fixed Time/DateTime conversions

---
 spec/ruby/library/datetime/to_time_spec.rb | 13 +++++++++++++
 spec/ruby/library/time/to_datetime_spec.rb | 13 +++++++++++++
 2 files changed, 26 insertions(+)

diff --git a/spec/ruby/library/datetime/to_time_spec.rb b/spec/ruby/library/datetime/to_time_spec.rb
index a03ab67867..88a7aaa739 100644
--- a/spec/ruby/library/datetime/to_time_spec.rb
+++ b/spec/ruby/library/datetime/to_time_spec.rb
@@ -18,6 +18,19 @@ describe "DateTime#to_time" do https://github.com/ruby/ruby/blob/trunk/spec/ruby/library/datetime/to_time_spec.rb#L18
     time.sec.should == 59
   end
 
+  version_is(Date::VERSION, '3.2.3') do
+    it "returns a Time representing the same instant before Gregorian" do
+      datetime = DateTime.civil(1582, 10, 4, 23, 58, 59)
+      time = datetime.to_time.utc
+      time.year.should == 1582
+      time.month.should == 10
+      time.day.should == 14
+      time.hour.should == 23
+      time.min.should == 58
+      time.sec.should == 59
+    end
+  end
+
   it "preserves the same time regardless of local time or zone" do
     date = DateTime.new(2012, 12, 24, 12, 23, 00, '+03:00')
 
diff --git a/spec/ruby/library/time/to_datetime_spec.rb b/spec/ruby/library/time/to_datetime_spec.rb
index 2c1e060f0f..c5561535b2 100644
--- a/spec/ruby/library/time/to_datetime_spec.rb
+++ b/spec/ruby/library/time/to_datetime_spec.rb
@@ -13,6 +13,19 @@ describe "Time#to_datetime" do https://github.com/ruby/ruby/blob/trunk/spec/ruby/library/time/to_datetime_spec.rb#L13
     datetime.sec.should == 59
   end
 
+  version_is(Date::VERSION, '3.2.3') do
+    it "returns a DateTime representing the same instant before Gregorian" do
+      time = Time.utc(1582, 10, 14, 23, 58, 59)
+      datetime = time.to_datetime
+      datetime.year.should == 1582
+      datetime.month.should == 10
+      datetime.day.should == 4
+      datetime.hour.should == 23
+      datetime.min.should == 58
+      datetime.sec.should == 59
+    end
+  end
+
   it "roundtrips" do
     time = Time.utc(3, 12, 31, 23, 58, 59)
     datetime = time.to_datetime
-- 
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