Make sendPolicyAnnouncementJob more robust

app/Jobs/SendPolicyAnnouncementJob.php

@@ -4,22 +4,30 @@
 
 use App\Notifications\PolicyAnnouncementNotification;
 use App\User;
-use Illuminate\Support\Facades\Notification;
+use Illuminate\Support\Facades\Log;
 
 /**
  * WARNING: This job is NOT idempotent. DO NOT RUN IT MULTIPLE TIMES.
  * There is also no error handling or mechanism for recording which users have been sent an email.
  *
- * This has created an issue on production where a user with an empty string as an email address
+ * This has created an issue on production where a user with a weird string as an email address
  * (due to a request to remove PII) caused Notification::send() to throw an error and the remaining
  * emails to not be sent.
  *
  * DO NOT REPEAT THIS PATTERN FOR OTHER JOBS
  */
 class SendPolicyAnnouncementJob extends Job {
-    public function handle() {
+    public function handle(): void {
         $users = User::query()->whereNotNull('email')->get();
 
-        Notification::send($users, new PolicyAnnouncementNotification());
+        $users->each(function (User $user) {
+            try {
+                $user->notify(new PolicyAnnouncementNotification());
+
+                Log::info('PolicyAnnouncementNotification sent successfully', [$user->id, $user->email]);
+            } catch (\Exception $exception) {
+                Log::error($exception->getMessage(), [$user->id, $user->email]);
+            }
+        });
     }
 }

tests/Jobs/SendPolicyAnnouncementJobTest.php

@@ -7,6 +7,7 @@
 use App\User;
 use Illuminate\Foundation\Testing\RefreshDatabase;
 use Illuminate\Support\Facades\Notification;
+use Symfony\Component\Mime\Exception\RfcComplianceException;
 use Tests\TestCase;
 
 class SendPolicyAnnouncementJobTest extends TestCase {
@@ -26,4 +27,24 @@ public function testThePolicyAnnouncementEmailToAllUsers() {
 
         Notification::assertSentTo($users, PolicyAnnouncementNotification::class);
     }
+
+    public function testItNotifiedAllUsersEvenIfMailerThrowsRfcComplianceException() {
+        // This test specifically simualtes the situation we saw in T432211#12270805
+        Notification::shouldReceive('send')
+            ->once()
+            ->andThrow(new RfcComplianceException());
+        Notification::shouldReceive('send')
+            ->atLeast()
+            ->times(3);
+
+        User::factory()->createMany([
+            ['email' => 'asdfghjklertyuiopcvbnm'],
+            ['email' => 'user1@email.com'],
+            ['email' => 'user2@email.com'],
+            ['email' => ''],
+            ['email' => 'user5@email.com'],
+        ]);
+        $job = new SendPolicyAnnouncementJob();
+        $job->handle();
+    }
 }