Add additional deletion tests and make them green

app/models/bulk_deletion_request.rb

@@ -44,7 +44,7 @@ def deliver_emails
   #
   # @return [void]
   def generate_emails
-    Company.all.find_each.with_index do |company, index|
+    Company.all.group(:email).find_each.with_index do |company, index|
       deletion_request = DeletionRequest.new \
         company: company,
         smtp_config: smtp_config,

test/integration/deletion_request_flows_test.rb

@@ -29,6 +29,39 @@ class DeletionRequestFlowsTest < ActionDispatch::IntegrationTest
     assert_emails 2
   end
 
+  # It's possible for multiple companies to have the same contact email address
+  # whether it's because there are umbrella companies at play or something else.
+  # We should prevent duplicate emails so we're not requesting multiple times.
+  test "only one email per unique email address is sent" do
+    # Creating an extra California data broker company separate from fixtures.
+    Company.create! \
+      category: "california_data_broker",
+      email: "test-ca-broker-2@localhost",
+      name: "Test CA Broker 2",
+      website: "https://test-ca-broker-2.localhost"
+    # Creating another California data broker company with the same email address.
+    Company.create! \
+      category: "california_data_broker",
+      email: "test-ca-broker-2@localhost", # SAME
+      name: "Test CA Broker 3",
+      website: "https://test-ca-broker-3.localhost"
+
+    post \
+      bulk_deletion_requests_path,
+      params: {
+        email_subject: "Test deletion request subject",
+        email_body: "Test deletion request body",
+        smtp_provider: "gmail",
+        smtp_username: "test_username",
+        smtp_password: "test_password"
+      }
+
+    # The first email should be delivered immediately, and there should only be one
+    # more queued email to ensure we deduplicated email addresses.
+    assert_emails 1
+    assert_enqueued_emails 1
+  end
+
   test "sets alert flash for invalid requests" do
     post \
       bulk_deletion_requests_path,
@@ -42,4 +75,25 @@ class DeletionRequestFlowsTest < ActionDispatch::IntegrationTest
 
     assert_equal ["Smtp config is missing or invalid"], flash[:alert]
   end
+
+  test "sets alert flash for SMTP authentication errors" do
+    bulk_deletion_request_mock = Mocktail.of_next BulkDeletionRequest
+    Mocktail
+      .stubs { bulk_deletion_request_mock.deliver_emails }
+      .with { raise Net::SMTPAuthenticationError.new("test") }
+
+    post \
+      bulk_deletion_requests_path,
+      params: {
+        email_subject: "Test deletion request subject",
+        email_body: "Test deletion request body",
+        smtp_provider: "gmail",
+        smtp_username: "test_username",
+        smtp_password: "test_password"
+      }
+
+    assert_equal \
+      "SMTP authentication failed. Please check your SMTP username and password.",
+      flash[:alert]
+  end
 end

test/test_helper.rb

@@ -19,6 +19,12 @@ class TestCase
     # Setup all fixtures in test/fixtures/*.yml for all tests in alphabetical order.
     fixtures :all
 
-    # Add more helper methods to be used by all tests here...
+    # Reset test states after each test.
+    #
+    # @return [void]
+    def teardown
+      super
+      Mocktail.reset
+    end
   end
 end