diff --git a/spec/chrono_model/time_machine/as_of_spec.rb b/spec/chrono_model/time_machine/as_of_spec.rb
index bb22e107..73e7cc9a 100644
--- a/spec/chrono_model/time_machine/as_of_spec.rb
+++ b/spec/chrono_model/time_machine/as_of_spec.rb
@@ -147,6 +147,8 @@
       it { expect(Foo.as_of($t.subbar.ts[1]).includes(:bars, :sub_bars).first.sub_bars.first.name).to eq 'bar sub-bar' }
       it { expect(Foo.as_of($t.subbar.ts[2]).includes(:bars, :sub_bars).first.sub_bars.first.name).to eq 'sub-bar sub-bar' }
       it { expect(Foo.as_of($t.subbar.ts[3]).includes(:bars, :sub_bars).first.sub_bars.first.name).to eq 'new sub-bar' }
+
+      it { expect(Foo.as_of(Time.now).includes(:bars, :sub_bars, :sub_sub_bars).first.sub_sub_bars.compact.size).to eq 1 }
     end
 
     it 'does not raise RecordNotFound when no history records are found' do
diff --git a/spec/support/time_machine/structure.rb b/spec/support/time_machine/structure.rb
index 1877772e..802c78bd 100644
--- a/spec/support/time_machine/structure.rb
+++ b/spec/support/time_machine/structure.rb
@@ -30,6 +30,7 @@ class ::Foo < ActiveRecord::Base
 
     has_many :bars
     has_many :sub_bars, through: :bars
+    has_many :sub_sub_bars, through: :sub_bars
 
     belongs_to :goo, class_name: 'FooGoo', optional: true
   end
@@ -93,10 +94,22 @@ class ::SubBar < ActiveRecord::Base
     include ChronoModel::TimeMachine
 
     belongs_to :bar
+    has_many :sub_sub_bars
 
     has_timeline with: :bar
   end
 
+  adapter.create_table 'sub_sub_bars', temporal: true do |t|
+    t.string     :name
+    t.references :sub_bar
+  end
+
+  class ::SubSubBar < ActiveRecord::Base
+    include ChronoModel::TimeMachine
+
+    belongs_to :sub_bar
+  end
+
   adapter.create_table 'bazs' do |t|
     t.string     :name
     t.references :bar
@@ -126,6 +139,8 @@ class ::Baz < ActiveRecord::Base
   $t.subbar = ts_eval { SubBar.create! name: 'sub-bar', bar: $t.bar }
   ts_eval($t.subbar) { update! name: 'bar sub-bar' }
 
+  ts_eval { SubSubBar.create! name: 'sub-sub-bar', sub_bar: $t.subbar }
+
   ts_eval($t.foo) { update! name: 'new foo' }
 
   ts_eval($t.bar) { update! name: 'bar bar' }