Validate when trying to generate trial license for a second time

app/controllers/admin/trials_controller.rb

@@ -40,8 +40,22 @@ class Admin::TrialsController < Admin::ApplicationController
   end
 
   def check_presence_of_license
-    if License.current&.active?
-      redirect_to admin_license_url, alert: 'You already have an active license key installed on this server.'
+    if error_message.present?
+      redirect_to admin_license_url, alert: error_message.html_safe
     end
   end
+
+  private
+
+  def error_message
+    @message ||= if License.trial.present?
+                   <<~MSG
+                     You have already used a free trial, if you want to extend it please contact us at
+                     <a href="mailto:sales@gitlab.com">sales@gitlab.com</a>
+                   MSG
+                 elsif License.current&.active?
+                   'You already have an active license key installed on this server.'
+                 end
+  end
+
 end

app/models/license.rb

@@ -166,6 +166,10 @@ class License < ActiveRecord::Base
       return unless license && license.valid?
       license
     end
+
+    def trial
+      all.detect { |license| license.trial? }
+    end
   end
 
   def data_filename

spec/features/admin/admin_trial_spec.rb

+require 'spec_helper'
+
+feature "Creating trial license", feature: true do
+  before do
+    gitlab_sign_in :admin
+  end
+
+  describe 'GET /admin/trials/new' do
+    context 'without a previous trial license' do
+      let!(:license_data) { create(:license, trial: true).data }
+      let(:body) do
+        { 'license_key' => license_data }
+      end
+
+      before { License.destroy_all }
+
+      it 'allows the creation of the trial license' do
+        stub_request(:post, "#{Gitlab::SUBSCRIPTIONS_URL}/trials")
+          .to_return(body: JSON(body), status: 200, headers: { 'Content-Type' => 'application/json' })
+
+        visit new_admin_trials_path
+
+        fill_in :first_name, with: 'John'
+        fill_in :last_name, with: 'Doe'
+        fill_in :work_email, with: 'john@local.dev'
+        fill_in :company_name, with: 'GitLab'
+        fill_in :phone_number, with: '111-111111'
+        fill_in :number_of_developers, with: 50
+        fill_in :number_of_users, with: 100
+        select('United States', from: 'Country')
+
+        click_button 'Start your free trial'
+
+        expect(page).to have_content('Your trial license was successfully activated')
+      end
+    end
+
+    context 'with an active license' do
+      it 'does not render the form and shows an error' do
+        create(:license)
+
+        visit new_admin_trials_path
+
+        expect(page).to have_content('You already have an active license key installed on this server')
+      end
+    end
+
+    context 'with a previous expired trial license' do
+      it 'does not render the form and shows an error' do
+        create(:license, trial: true, expired: true)
+
+        visit new_admin_trials_path
+
+        expect(page).to have_content('You have already used a free trial')
+      end
+    end
+
+  end
+end