diff --git a/spec/lib/tasks/2019_08_22_migrate_attestation_files_spec.rb b/spec/lib/tasks/2019_08_22_migrate_attestation_files_spec.rb
new file mode 100644
index 000000000..5a697ec47
--- /dev/null
+++ b/spec/lib/tasks/2019_08_22_migrate_attestation_files_spec.rb
@@ -0,0 +1,128 @@
+describe '2019_08_22_migrate_attestation_files.rake' do
+  let(:rake_task) { Rake::Task["2019_08_22_migrate_attestation_files:#{sub_task}"] }
+
+  let(:run_task) do
+    rake_task.invoke
+    models.each(&:reload)
+  end
+
+  after do
+    ENV['LIMIT'] = nil
+    rake_task.reenable
+  end
+
+  context 'attestation' do
+    let(:models) do
+      [
+        create(:attestation, created_at: 3.days.ago),
+        create(:attestation, :with_legacy_pdf, created_at: 2.days.ago),
+        create(:attestation, :with_legacy_pdf, created_at: 1.day.ago)
+      ]
+    end
+
+    before do
+      first_attestation = models[0]
+      expect(first_attestation.pdf.present?).to be_falsey
+      expect(first_attestation.read_attribute(:pdf)).to be_nil
+
+      models.each do |attestation|
+        if attestation.pdf.present?
+          stub_request(:get, attestation.pdf_url)
+            .to_return(status: 200, body: File.read(attestation.pdf.path))
+        end
+      end
+    end
+
+    context 'pdf' do
+      let(:sub_task) { 'migrate_attestation_pdf' }
+
+      it 'should migrate pdf' do
+        expect(models.map(&:pdf_active_storage).map(&:attached?)).to eq([false, false, false])
+
+        run_task
+
+        expect(Attestation.where(pdf: nil).count).to eq(1)
+        expect(models.map(&:pdf_active_storage).map(&:attached?)).to eq([false, true, true])
+      end
+
+      it 'should migrate pdf within limit' do
+        expect(models.map(&:pdf_active_storage).map(&:attached?)).to eq([false, false, false])
+
+        ENV['LIMIT'] = '1'
+        run_task
+
+        expect(Attestation.where(pdf: nil).count).to eq(1)
+        expect(models.map(&:pdf_active_storage).map(&:attached?)).to eq([false, true, false])
+      end
+    end
+  end
+
+  context 'attestation_templates' do
+    let(:models) do
+      [
+        create(:attestation_template),
+        create(:attestation_template, :with_legacy_files),
+        create(:attestation_template, :with_legacy_files)
+      ]
+    end
+
+    before do
+      models.each do |attestation_template|
+        if attestation_template.logo.present?
+          stub_request(:get, attestation_template.logo_url)
+            .to_return(status: 200, body: File.read(attestation_template.logo.path))
+        end
+        if attestation_template.signature.present?
+          stub_request(:get, attestation_template.signature_url)
+            .to_return(status: 200, body: File.read(attestation_template.signature.path))
+        end
+      end
+    end
+
+    context 'logo' do
+      let(:sub_task) { 'migrate_attestation_template_logo' }
+
+      it 'should migrate logo' do
+        expect(models.map(&:logo_active_storage).map(&:attached?)).to eq([false, false, false])
+
+        run_task
+
+        expect(AttestationTemplate.where(logo: nil).count).to eq(1)
+        expect(models.map(&:logo_active_storage).map(&:attached?)).to eq([false, true, true])
+      end
+
+      it 'should migrate logo within limit' do
+        expect(models.map(&:logo_active_storage).map(&:attached?)).to eq([false, false, false])
+
+        ENV['LIMIT'] = '1'
+        run_task
+
+        expect(AttestationTemplate.where(logo: nil).count).to eq(1)
+        expect(models.map(&:logo_active_storage).map(&:attached?)).to eq([false, true, false])
+      end
+    end
+
+    context 'signature' do
+      let(:sub_task) { 'migrate_attestation_template_signature' }
+
+      it 'should migrate signature' do
+        expect(models.map(&:signature_active_storage).map(&:attached?)).to eq([false, false, false])
+
+        run_task
+
+        expect(AttestationTemplate.where(signature: nil).count).to eq(1)
+        expect(models.map(&:signature_active_storage).map(&:attached?)).to eq([false, true, true])
+      end
+
+      it 'should migrate signature within limit' do
+        expect(models.map(&:signature_active_storage).map(&:attached?)).to eq([false, false, false])
+
+        ENV['LIMIT'] = '1'
+        run_task
+
+        expect(AttestationTemplate.where(signature: nil).count).to eq(1)
+        expect(models.map(&:signature_active_storage).map(&:attached?)).to eq([false, true, false])
+      end
+    end
+  end
+end