diff --git a/app/views/reports/_learning_times.html.slim b/app/views/reports/_learning_times.html.slim
index 894fba8e7db..306771f4699 100644
--- a/app/views/reports/_learning_times.html.slim
+++ b/app/views/reports/_learning_times.html.slim
@@ -10,4 +10,4 @@
     ul.learning-times__items
       - @report.learning_times.each do |learning_time|
         li.learning-times__item
-          | #{l learning_time.started_at, format: :time_only} 〜 #{'(翌日)' if learning_time.started_at.day < learning_time.finished_at.day}#{l learning_time.finished_at, format: :time_only}
+          | #{l learning_time.started_at, format: :time_only} 〜 #{'(翌日)' if learning_time.started_at.to_date < learning_time.finished_at.to_date}#{l learning_time.finished_at, format: :time_only}
diff --git a/test/system/reports_test.rb b/test/system/reports_test.rb
index 4091521e40e..1d4659b1661 100644
--- a/test/system/reports_test.rb
+++ b/test/system/reports_test.rb
@@ -277,6 +277,23 @@ class ReportsTest < ApplicationSystemTestCase
     assert_text '00:30 〜 02:30'
   end
 
+  test 'learning times when carrying over next month' do
+    visit_with_auth '/reports/new', 'komagata'
+    fill_in 'report_title', with: 'テスト日報'
+    fill_in 'report_description', with: '学習時間が月を跨いでいるパターン'
+    fill_in 'report_reported_on', with: Date.new(2024, 1, 31)
+
+    all('.learning-time')[0].all('.learning-time__started-at select')[0].select('22')
+    all('.learning-time')[0].all('.learning-time__started-at select')[1].select('00')
+    all('.learning-time')[0].all('.learning-time__finished-at select')[0].select('00')
+    all('.learning-time')[0].all('.learning-time__finished-at select')[1].select('00')
+
+    click_button '提出'
+
+    assert_text "2時間\n"
+    assert_text '22:00 〜 (翌日)00:00'
+  end
+
   test 'learning times order' do
     visit_with_auth '/reports/new', 'komagata'
     fill_in 'report_title', with: 'テスト日報'