diff --git a/activerecord/lib/active_record/associations/preloader/association.rb b/activerecord/lib/active_record/associations/preloader/association.rb
index 4c7b0e6f07..5c68e2e3be 100644
--- a/activerecord/lib/active_record/associations/preloader/association.rb
+++ b/activerecord/lib/active_record/associations/preloader/association.rb
@@ -38,7 +38,24 @@ def records_by_owner
 
         def preloaded_records
           return @preloaded_records if defined?(@preloaded_records)
-          @preloaded_records = owner_keys.empty? ? [] : records_for(owner_keys)
+
+          raw_records = owner_keys.empty? ? [] : records_for(owner_keys)
+          seen_records_by_owner = {}.compare_by_identity
+
+          @preloaded_records = raw_records.select do |record|
+            assignments = []
+
+            owners_by_key[convert_key(record[association_key_name])].each do |owner|
+              entries = (seen_records_by_owner[owner] ||= [])
+
+              if reflection.collection? || entries.empty?
+                entries << record
+                assignments << record
+              end
+            end
+
+            !assignments.empty?
+          end
         end
 
         private
diff --git a/activerecord/test/cases/associations/cascaded_eager_loading_test.rb b/activerecord/test/cases/associations/cascaded_eager_loading_test.rb
index 055a62b2bc..002962c3f9 100644
--- a/activerecord/test/cases/associations/cascaded_eager_loading_test.rb
+++ b/activerecord/test/cases/associations/cascaded_eager_loading_test.rb
@@ -200,4 +200,46 @@ def test_preloaded_records_are_not_duplicated
 
     assert_equal expected, actual
   end
+
+  def test_preloading_across_has_one_constrains_loaded_records
+    author = authors(:david)
+
+    old_post = author.posts.create!(title: "first post", body: "test")
+    old_post.comments.create!(author: authors(:mary), body: "a response")
+
+    recent_post = author.posts.create!(title: "first post", body: "test")
+    last_comment = recent_post.comments.create!(author: authors(:bob), body: "a response")
+
+    authors = Author.where(id: author.id)
+    retrieved_comments = []
+
+    reset_callbacks(Comment, :initialize) do
+      Comment.after_initialize { |record| retrieved_comments << record }
+      authors.preload(recent_post: :comments).load
+    end
+
+    assert_equal 1, retrieved_comments.size
+    assert_equal [last_comment], retrieved_comments
+  end
+
+  def test_preloading_across_has_one_through_constrains_loaded_records
+    author = authors(:david)
+
+    old_post = author.posts.create!(title: "first post", body: "test")
+    old_post.comments.create!(author: authors(:mary), body: "a response")
+
+    recent_post = author.posts.create!(title: "first post", body: "test")
+    recent_post.comments.create!(author: authors(:bob), body: "a response")
+
+    authors = Author.where(id: author.id)
+    retrieved_authors = []
+
+    reset_callbacks(Author, :initialize) do
+      Author.after_initialize { |record| retrieved_authors << record }
+      authors.preload(recent_response: :author).load
+    end
+
+    assert_equal 2, retrieved_authors.size
+    assert_equal [author, authors(:bob)], retrieved_authors
+  end
 end
diff --git a/activerecord/test/models/author.rb b/activerecord/test/models/author.rb
index fef3671253..a8ddc86bdb 100644
--- a/activerecord/test/models/author.rb
+++ b/activerecord/test/models/author.rb
@@ -160,6 +160,9 @@ def ratings
   has_many :posts_with_signature, ->(record) { where("posts.title LIKE ?", "%by #{record.name.downcase}%") }, class_name: "Post"
   has_many :posts_mentioning_author, ->(record = nil) { where("posts.body LIKE ?", "%#{record&.name&.downcase}%") }, class_name: "Post"
 
+  has_one :recent_post, -> { order(id: :desc) }, class_name: "Post"
+  has_one :recent_response, through: :recent_post, source: :comments
+
   has_many :posts_with_extension, -> { order(:title) }, class_name: "Post" do
     def extension_method; end
   end