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diff --git a/spec/lib/gitlab/background_migration/legacy_upload_mover_spec.rb b/spec/lib/gitlab/background_migration/legacy_upload_mover_spec.rb
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+++ b/spec/lib/gitlab/background_migration/legacy_upload_mover_spec.rb
@@ -0,0 +1,296 @@
+# frozen_string_literal: true
+require 'spec_helper'
+
+# rubocop: disable RSpec/FactoriesInMigrationSpecs
+describe Gitlab::BackgroundMigration::LegacyUploadMover do
+  let(:test_dir) { FileUploader.options['storage_path'] }
+  let(:filename) { 'image.png' }
+
+  let!(:namespace) { create(:namespace) }
+  let!(:legacy_project) { create(:project, :legacy_storage, namespace: namespace) }
+  let!(:hashed_project) { create(:project, namespace: namespace) }
+  # default project
+  let(:project) { legacy_project }
+
+  let!(:issue) { create(:issue, project: project) }
+  let!(:note) { create(:note, note: 'some note', project: project, noteable: issue) }
+
+  let(:legacy_upload) { create_upload(note, filename) }
+
+  def create_remote_upload(model, filename)
+    create(:upload, :attachment_upload,
+           path: "note/attachment/#{model.id}/#{filename}", secret: nil,
+           store: ObjectStorage::Store::REMOTE, model: model)
+  end
+
+  def create_upload(model, filename, with_file = true)
+    params = {
+      path: "uploads/-/system/note/attachment/#{model.id}/#{filename}",
+      model: model,
+      store: ObjectStorage::Store::LOCAL
+    }
+
+    if with_file
+      upload = create(:upload, :with_file, :attachment_upload, params)
+      model.update(attachment: upload.build_uploader)
+      model.attachment.upload
+    else
+      create(:upload, :attachment_upload, params)
+    end
+  end
+
+  def new_upload
+    Upload.find_by(model_id: project.id, model_type: 'Project')
+  end
+
+  def expect_error_log
+    expect_next_instance_of(Gitlab::BackgroundMigration::Logger) do |logger|
+      expect(logger).to receive(:warn)
+    end
+  end
+
+  shared_examples 'legacy upload deletion' do
+    it 'removes the upload record' do
+      described_class.new(legacy_upload).execute
+
+      expect { legacy_upload.reload }.to raise_error(ActiveRecord::RecordNotFound)
+    end
+  end
+
+  shared_examples 'move error' do
+    it 'does not remove the upload file' do
+      expect_error_log
+
+      described_class.new(legacy_upload).execute
+
+      expect(legacy_upload.reload).to eq(legacy_upload)
+    end
+  end
+
+  shared_examples 'migrates the file correctly' do
+    before do
+      described_class.new(legacy_upload).execute
+    end
+
+    it 'creates a new uplaod record correctly' do
+      expect(new_upload.secret).not_to be_nil
+      expect(new_upload.path).to end_with("#{new_upload.secret}/image.png")
+      expect(new_upload.model_id).to eq(project.id)
+      expect(new_upload.model_type).to eq('Project')
+      expect(new_upload.uploader).to eq('FileUploader')
+    end
+
+    it 'updates the legacy upload note so that it references the file in the markdown' do
+      expected_path = File.join('/uploads', new_upload.secret, 'image.png')
+      expected_markdown = "some note \n ![image](#{expected_path})"
+      expect(note.reload.note).to eq(expected_markdown)
+    end
+
+    it 'removes the attachment from the note model' do
+      expect(note.reload.attachment.file).to be_nil
+    end
+  end
+
+  context 'when no model found for the upload' do
+    before do
+      legacy_upload.model = nil
+      expect_error_log
+    end
+
+    it_behaves_like 'legacy upload deletion'
+  end
+
+  context 'when the upload move fails' do
+    before do
+      expect(FileUploader).to receive(:copy_to).and_raise('failed')
+    end
+
+    it_behaves_like 'move error'
+  end
+
+  context 'when the upload is in local storage' do
+    shared_examples 'legacy local file' do
+      it 'removes the file correctly' do
+        expect(File.exist?(legacy_upload.absolute_path)).to be_truthy
+
+        described_class.new(legacy_upload).execute
+
+        expect(File.exist?(legacy_upload.absolute_path)).to be_falsey
+      end
+
+      it 'moves legacy uploads to the correct location' do
+        described_class.new(legacy_upload).execute
+
+        expected_path = File.join(test_dir, 'uploads', project.disk_path, new_upload.secret, filename)
+        expect(File.exist?(expected_path)).to be_truthy
+      end
+    end
+
+    context 'when the upload file does not exist on the filesystem' do
+      let(:legacy_upload) { create_upload(note, filename, false) }
+
+      before do
+        expect_error_log
+      end
+
+      it_behaves_like 'legacy upload deletion'
+    end
+
+    context 'when an upload belongs to a legacy_diff_note' do
+      let!(:merge_request) { create(:merge_request, source_project: project) }
+      let!(:note) do
+        create(:legacy_diff_note_on_merge_request,
+          note: 'some note', project: project, noteable: merge_request)
+      end
+      let(:legacy_upload) do
+        create(:upload, :with_file, :attachment_upload,
+               path: "uploads/-/system/note/attachment/#{note.id}/#{filename}", model: note)
+      end
+
+      context 'when the file does not exist for the upload' do
+        let(:legacy_upload) do
+          create(:upload, :attachment_upload,
+                 path: "uploads/-/system/note/attachment/#{note.id}/#{filename}", model: note)
+        end
+
+        it_behaves_like 'move error'
+      end
+
+      context 'when the file does not exist on expected path' do
+        let(:legacy_upload) do
+          create(:upload, :attachment_upload, :with_file,
+                 path: "uploads/-/system/note/attachment/some_part/#{note.id}/#{filename}", model: note)
+        end
+
+        it_behaves_like 'move error'
+      end
+
+      context 'when the file path does not include system/note/attachment' do
+        let(:legacy_upload) do
+          create(:upload, :attachment_upload, :with_file,
+                 path: "uploads/-/system#{note.id}/#{filename}", model: note)
+        end
+
+        it_behaves_like 'move error'
+      end
+
+      context 'when the file move raises an error' do
+        before do
+          allow(FileUtils).to receive(:mv).and_raise(Errno::EACCES)
+        end
+
+        it_behaves_like 'move error'
+      end
+
+      context 'when the file can be handled correctly' do
+        it_behaves_like 'migrates the file correctly'
+        it_behaves_like 'legacy local file'
+        it_behaves_like 'legacy upload deletion'
+      end
+    end
+
+    context 'when object storage is disabled for FileUploader' do
+      context 'when the file belongs to a legacy project' do
+        let(:project) { legacy_project }
+
+        it_behaves_like 'migrates the file correctly'
+        it_behaves_like 'legacy local file'
+        it_behaves_like 'legacy upload deletion'
+      end
+
+      context 'when the file belongs to a hashed project' do
+        let(:project) { hashed_project }
+
+        it_behaves_like 'migrates the file correctly'
+        it_behaves_like 'legacy local file'
+        it_behaves_like 'legacy upload deletion'
+      end
+    end
+
+    context 'when object storage is enabled for FileUploader' do
+      # The process of migrating to object storage is a manual one,
+      # so it would go against expectations to automatically migrate these files
+      # to object storage during this migration.
+      # After this migration, these files should be able to successfully migrate to object storage.
+
+      before do
+        stub_uploads_object_storage(FileUploader)
+      end
+
+      context 'when the file belongs to a legacy project' do
+        let(:project) { legacy_project }
+
+        it_behaves_like 'migrates the file correctly'
+        it_behaves_like 'legacy local file'
+        it_behaves_like 'legacy upload deletion'
+      end
+
+      context 'when the file belongs to a hashed project' do
+        let(:project) { hashed_project }
+
+        it_behaves_like 'migrates the file correctly'
+        it_behaves_like 'legacy local file'
+        it_behaves_like 'legacy upload deletion'
+      end
+    end
+  end
+
+  context 'when legacy uploads are stored in object storage' do
+    let(:legacy_upload) { create_remote_upload(note, filename) }
+    let(:remote_file) do
+      { key: "#{legacy_upload.path}" }
+    end
+    let(:connection) { ::Fog::Storage.new(FileUploader.object_store_credentials) }
+    let(:bucket) { connection.directories.create(key: 'uploads') }
+
+    before do
+      stub_uploads_object_storage(FileUploader)
+    end
+
+    shared_examples 'legacy remote file' do
+      it 'removes the file correctly' do
+        # expect(bucket.files.get(remote_file[:key])).to be_nil
+
+        described_class.new(legacy_upload).execute
+
+        expect(bucket.files.get(remote_file[:key])).to be_nil
+      end
+
+      it 'moves legacy uploads to the correct remote location' do
+        described_class.new(legacy_upload).execute
+
+        connection = ::Fog::Storage.new(FileUploader.object_store_credentials)
+        expect(connection.get_object('uploads', new_upload.path)[:status]).to eq(200)
+      end
+    end
+
+    context 'when the upload file does not exist on the filesystem' do
+      it_behaves_like 'legacy upload deletion'
+    end
+
+    context 'when the file belongs to a legacy project' do
+      before do
+        bucket.files.create(remote_file)
+      end
+
+      let(:project) { legacy_project }
+
+      it_behaves_like 'migrates the file correctly'
+      it_behaves_like 'legacy remote file'
+      it_behaves_like 'legacy upload deletion'
+    end
+
+    context 'when the file belongs to a hashed project' do
+      before do
+        bucket.files.create(remote_file)
+      end
+
+      let(:project) { hashed_project }
+
+      it_behaves_like 'migrates the file correctly'
+      it_behaves_like 'legacy remote file'
+      it_behaves_like 'legacy upload deletion'
+    end
+  end
+end
+# rubocop: enable RSpec/FactoriesInMigrationSpecs