From 12fbd22459d3db1d6f08ccce48c56c1e756d789d Mon Sep 17 00:00:00 2001
From: Dan Lemon <daniel.lemon@amazee.io>
Date: Wed, 1 Jul 2026 11:18:10 +0200
Subject: [PATCH 1/2] fix: send trial emails synchronously so sent flag
 reflects delivery

---
 .../Trial/ProcessMidtrialEmailJob.php         |  2 +-
 .../Trial/ProcessOneDayLeftEmailJob.php       |  2 +-
 .../Trial/ProcessTrialCompleteEmailJob.php    |  2 +-
 .../ProcessTrialCompleteEmailJobTest.php      | 97 +++++++++++++++++++
 4 files changed, 100 insertions(+), 3 deletions(-)
 create mode 100644 tests/Feature/Jobs/Trial/ProcessTrialCompleteEmailJobTest.php

diff --git a/app/Jobs/ProcessPolydockAppInstanceJobs/Trial/ProcessMidtrialEmailJob.php b/app/Jobs/ProcessPolydockAppInstanceJobs/Trial/ProcessMidtrialEmailJob.php
index f61fd2ed..5a68a170 100644
--- a/app/Jobs/ProcessPolydockAppInstanceJobs/Trial/ProcessMidtrialEmailJob.php
+++ b/app/Jobs/ProcessPolydockAppInstanceJobs/Trial/ProcessMidtrialEmailJob.php
@@ -77,7 +77,7 @@ public function handle()
                     'app_instance_id' => $this->appInstance->id,
                 ]);
 
-                $mail->queue(new AppInstanceMidtrialMail($this->appInstance, $owner));
+                $mail->send(new AppInstanceMidtrialMail($this->appInstance, $owner));
             }
         } else {
             $this->appInstance->info('Trial expired, skipping midtrial email but marking as sent', [
diff --git a/app/Jobs/ProcessPolydockAppInstanceJobs/Trial/ProcessOneDayLeftEmailJob.php b/app/Jobs/ProcessPolydockAppInstanceJobs/Trial/ProcessOneDayLeftEmailJob.php
index 150cb1fd..e5b9dc00 100644
--- a/app/Jobs/ProcessPolydockAppInstanceJobs/Trial/ProcessOneDayLeftEmailJob.php
+++ b/app/Jobs/ProcessPolydockAppInstanceJobs/Trial/ProcessOneDayLeftEmailJob.php
@@ -65,7 +65,7 @@ public function handle()
                     'app_instance_id' => $this->appInstance->id,
                 ]);
 
-                $mail->queue(new AppInstanceOneDayLeftMail($this->appInstance, $owner));
+                $mail->send(new AppInstanceOneDayLeftMail($this->appInstance, $owner));
             }
         } else {
             $this->appInstance->info('Trial expired, skipping one day left email but marking as sent', [
diff --git a/app/Jobs/ProcessPolydockAppInstanceJobs/Trial/ProcessTrialCompleteEmailJob.php b/app/Jobs/ProcessPolydockAppInstanceJobs/Trial/ProcessTrialCompleteEmailJob.php
index 654ea4e7..5b79ad2c 100644
--- a/app/Jobs/ProcessPolydockAppInstanceJobs/Trial/ProcessTrialCompleteEmailJob.php
+++ b/app/Jobs/ProcessPolydockAppInstanceJobs/Trial/ProcessTrialCompleteEmailJob.php
@@ -53,7 +53,7 @@ public function handle()
                 'owner_email' => $owner->email,
             ]);
 
-            $mail->queue(new AppInstanceTrialCompleteMail($this->appInstance, $owner));
+            $mail->send(new AppInstanceTrialCompleteMail($this->appInstance, $owner));
         }
 
         // Update the sent flag
diff --git a/tests/Feature/Jobs/Trial/ProcessTrialCompleteEmailJobTest.php b/tests/Feature/Jobs/Trial/ProcessTrialCompleteEmailJobTest.php
new file mode 100644
index 00000000..2c1b36bb
--- /dev/null
+++ b/tests/Feature/Jobs/Trial/ProcessTrialCompleteEmailJobTest.php
@@ -0,0 +1,97 @@
+<?php
+
+namespace Tests\Feature\Jobs\Trial;
+
+use App\Enums\UserGroupRoleEnum;
+use App\Events\PolydockAppInstanceCreatedWithNewStatus;
+use App\Events\PolydockAppInstanceStatusChanged;
+use App\Jobs\ProcessPolydockAppInstanceJobs\Trial\ProcessTrialCompleteEmailJob;
+use App\Mail\AppInstanceTrialCompleteMail;
+use App\Models\PolydockAppInstance;
+use App\Models\PolydockStore;
+use App\Models\PolydockStoreApp;
+use App\Models\User;
+use App\Models\UserGroup;
+use App\Polydock\Apps\Generic\PolydockAiApp;
+use App\Polydock\Core\Enums\PolydockAppInstanceStatus;
+use Illuminate\Foundation\Testing\RefreshDatabase;
+use Illuminate\Support\Facades\Event;
+use Illuminate\Support\Facades\Mail;
+use Mockery;
+use RuntimeException;
+use Tests\TestCase;
+
+class ProcessTrialCompleteEmailJobTest extends TestCase
+{
+    use RefreshDatabase;
+
+    private PolydockAppInstance $instance;
+
+    protected function setUp(): void
+    {
+        parent::setUp();
+
+        // Prevent the NEW-status save below from dispatching the real
+        // lifecycle jobs (which would reach out to Lagoon).
+        Event::fake([
+            PolydockAppInstanceCreatedWithNewStatus::class,
+            PolydockAppInstanceStatusChanged::class,
+        ]);
+
+        $store = PolydockStore::factory()->create();
+        $storeApp = PolydockStoreApp::factory()->create([
+            'polydock_store_id' => $store->id,
+            'send_trial_complete_email' => true,
+        ]);
+
+        $group = UserGroup::factory()->create();
+        $owner = User::factory()->create(['email' => 'owner@example.com']);
+        $group->users()->attach($owner->id, ['role' => UserGroupRoleEnum::OWNER->value]);
+
+        $this->instance = new PolydockAppInstance;
+        $this->instance->polydock_store_app_id = $storeApp->id;
+        $this->instance->user_group_id = $group->id;
+        $this->instance->name = 'trial-complete-test';
+        $this->instance->app_type = PolydockAiApp::class;
+        $this->instance->status = PolydockAppInstanceStatus::NEW;
+        $this->instance->is_trial = true;
+        $this->instance->trial_ends_at = now()->subDay();
+        $this->instance->trial_complete_email_sent = false;
+        $this->instance->save();
+    }
+
+    public function test_trial_complete_email_is_sent_and_flag_is_set(): void
+    {
+        Mail::fake();
+
+        (new ProcessTrialCompleteEmailJob($this->instance->id))->handle();
+
+        Mail::assertSent(AppInstanceTrialCompleteMail::class);
+
+        $this->assertTrue($this->instance->fresh()->trial_complete_email_sent);
+    }
+
+    public function test_flag_stays_false_when_send_throws(): void
+    {
+        // Force the synchronous send to fail so the job should throw before
+        // the sent flag is updated.
+        $pendingMail = Mockery::mock();
+        $pendingMail->shouldReceive('cc')->andReturnSelf();
+        $pendingMail->shouldReceive('send')
+            ->andThrow(new RuntimeException('SMTP failure'));
+
+        Mail::shouldReceive('to')->andReturn($pendingMail);
+
+        try {
+            (new ProcessTrialCompleteEmailJob($this->instance->id))->handle();
+            $this->fail('Expected the job to propagate the send exception.');
+        } catch (RuntimeException $e) {
+            $this->assertSame('SMTP failure', $e->getMessage());
+        }
+
+        $this->assertFalse(
+            $this->instance->fresh()->trial_complete_email_sent,
+            'The sent flag must remain false when delivery fails so the job can retry.'
+        );
+    }
+}

From 6843faf3a15a3a38d9c9eb802cf8f8b634b111ef Mon Sep 17 00:00:00 2001
From: Dan Lemon <daniel.lemon@amazee.io>
Date: Wed, 1 Jul 2026 15:46:00 +0200
Subject: [PATCH 2/2] test: cover midtrial and one-day-left email jobs for the
 send/flag change

---
 .../Trial/ProcessMidtrialEmailJobTest.php     | 99 +++++++++++++++++++
 .../Trial/ProcessOneDayLeftEmailJobTest.php   | 99 +++++++++++++++++++
 2 files changed, 198 insertions(+)
 create mode 100644 tests/Feature/Jobs/Trial/ProcessMidtrialEmailJobTest.php
 create mode 100644 tests/Feature/Jobs/Trial/ProcessOneDayLeftEmailJobTest.php

diff --git a/tests/Feature/Jobs/Trial/ProcessMidtrialEmailJobTest.php b/tests/Feature/Jobs/Trial/ProcessMidtrialEmailJobTest.php
new file mode 100644
index 00000000..2ad7efa5
--- /dev/null
+++ b/tests/Feature/Jobs/Trial/ProcessMidtrialEmailJobTest.php
@@ -0,0 +1,99 @@
+<?php
+
+namespace Tests\Feature\Jobs\Trial;
+
+use App\Enums\UserGroupRoleEnum;
+use App\Events\PolydockAppInstanceCreatedWithNewStatus;
+use App\Events\PolydockAppInstanceStatusChanged;
+use App\Jobs\ProcessPolydockAppInstanceJobs\Trial\ProcessMidtrialEmailJob;
+use App\Mail\AppInstanceMidtrialMail;
+use App\Models\PolydockAppInstance;
+use App\Models\PolydockStore;
+use App\Models\PolydockStoreApp;
+use App\Models\User;
+use App\Models\UserGroup;
+use App\Polydock\Apps\Generic\PolydockAiApp;
+use App\Polydock\Core\Enums\PolydockAppInstanceStatus;
+use Illuminate\Foundation\Testing\RefreshDatabase;
+use Illuminate\Support\Facades\Event;
+use Illuminate\Support\Facades\Mail;
+use Mockery;
+use RuntimeException;
+use Tests\TestCase;
+
+class ProcessMidtrialEmailJobTest extends TestCase
+{
+    use RefreshDatabase;
+
+    private PolydockAppInstance $instance;
+
+    protected function setUp(): void
+    {
+        parent::setUp();
+
+        // Prevent the NEW-status save below from dispatching the real
+        // lifecycle jobs (which would reach out to Lagoon).
+        Event::fake([
+            PolydockAppInstanceCreatedWithNewStatus::class,
+            PolydockAppInstanceStatusChanged::class,
+        ]);
+
+        $store = PolydockStore::factory()->create();
+        $storeApp = PolydockStoreApp::factory()->create([
+            'polydock_store_id' => $store->id,
+            'send_midtrial_email' => true,
+        ]);
+
+        $group = UserGroup::factory()->create();
+        $owner = User::factory()->create(['email' => 'owner@example.com']);
+        $group->users()->attach($owner->id, ['role' => UserGroupRoleEnum::OWNER->value]);
+
+        $this->instance = new PolydockAppInstance;
+        $this->instance->polydock_store_app_id = $storeApp->id;
+        $this->instance->user_group_id = $group->id;
+        $this->instance->name = 'midtrial-test';
+        $this->instance->app_type = PolydockAiApp::class;
+        $this->instance->status = PolydockAppInstanceStatus::NEW;
+        $this->instance->is_trial = true;
+        // Reminder is due (past) but the trial itself has not expired (future).
+        $this->instance->send_midtrial_email_at = now()->subHour();
+        $this->instance->trial_ends_at = now()->addDays(3);
+        $this->instance->midtrial_email_sent = false;
+        $this->instance->save();
+    }
+
+    public function test_midtrial_email_is_sent_and_flag_is_set(): void
+    {
+        Mail::fake();
+
+        (new ProcessMidtrialEmailJob($this->instance->id))->handle();
+
+        Mail::assertSent(AppInstanceMidtrialMail::class);
+
+        $this->assertTrue($this->instance->fresh()->midtrial_email_sent);
+    }
+
+    public function test_flag_stays_false_when_send_throws(): void
+    {
+        // Force the synchronous send to fail so the job should throw before
+        // the sent flag is updated.
+        $pendingMail = Mockery::mock();
+        $pendingMail->shouldReceive('cc')->andReturnSelf();
+        $pendingMail->shouldReceive('send')
+            ->andThrow(new RuntimeException('SMTP failure'));
+
+        Mail::shouldReceive('to')->andReturn($pendingMail);
+
+        try {
+            (new ProcessMidtrialEmailJob($this->instance->id))->handle();
+            $this->fail('Expected the job to propagate the send exception.');
+        } catch (RuntimeException $e) {
+            $this->assertSame('SMTP failure', $e->getMessage());
+        }
+
+        $this->assertFalse(
+            $this->instance->fresh()->midtrial_email_sent,
+            'The sent flag must remain false when delivery fails so the job can retry.'
+        );
+    }
+}
diff --git a/tests/Feature/Jobs/Trial/ProcessOneDayLeftEmailJobTest.php b/tests/Feature/Jobs/Trial/ProcessOneDayLeftEmailJobTest.php
new file mode 100644
index 00000000..1f335a05
--- /dev/null
+++ b/tests/Feature/Jobs/Trial/ProcessOneDayLeftEmailJobTest.php
@@ -0,0 +1,99 @@
+<?php
+
+namespace Tests\Feature\Jobs\Trial;
+
+use App\Enums\UserGroupRoleEnum;
+use App\Events\PolydockAppInstanceCreatedWithNewStatus;
+use App\Events\PolydockAppInstanceStatusChanged;
+use App\Jobs\ProcessPolydockAppInstanceJobs\Trial\ProcessOneDayLeftEmailJob;
+use App\Mail\AppInstanceOneDayLeftMail;
+use App\Models\PolydockAppInstance;
+use App\Models\PolydockStore;
+use App\Models\PolydockStoreApp;
+use App\Models\User;
+use App\Models\UserGroup;
+use App\Polydock\Apps\Generic\PolydockAiApp;
+use App\Polydock\Core\Enums\PolydockAppInstanceStatus;
+use Illuminate\Foundation\Testing\RefreshDatabase;
+use Illuminate\Support\Facades\Event;
+use Illuminate\Support\Facades\Mail;
+use Mockery;
+use RuntimeException;
+use Tests\TestCase;
+
+class ProcessOneDayLeftEmailJobTest extends TestCase
+{
+    use RefreshDatabase;
+
+    private PolydockAppInstance $instance;
+
+    protected function setUp(): void
+    {
+        parent::setUp();
+
+        // Prevent the NEW-status save below from dispatching the real
+        // lifecycle jobs (which would reach out to Lagoon).
+        Event::fake([
+            PolydockAppInstanceCreatedWithNewStatus::class,
+            PolydockAppInstanceStatusChanged::class,
+        ]);
+
+        $store = PolydockStore::factory()->create();
+        $storeApp = PolydockStoreApp::factory()->create([
+            'polydock_store_id' => $store->id,
+            'send_one_day_left_email' => true,
+        ]);
+
+        $group = UserGroup::factory()->create();
+        $owner = User::factory()->create(['email' => 'owner@example.com']);
+        $group->users()->attach($owner->id, ['role' => UserGroupRoleEnum::OWNER->value]);
+
+        $this->instance = new PolydockAppInstance;
+        $this->instance->polydock_store_app_id = $storeApp->id;
+        $this->instance->user_group_id = $group->id;
+        $this->instance->name = 'one-day-left-test';
+        $this->instance->app_type = PolydockAiApp::class;
+        $this->instance->status = PolydockAppInstanceStatus::NEW;
+        $this->instance->is_trial = true;
+        // Reminder is due (past) but the trial itself has not expired (future).
+        $this->instance->send_one_day_left_email_at = now()->subHour();
+        $this->instance->trial_ends_at = now()->addDay();
+        $this->instance->one_day_left_email_sent = false;
+        $this->instance->save();
+    }
+
+    public function test_one_day_left_email_is_sent_and_flag_is_set(): void
+    {
+        Mail::fake();
+
+        (new ProcessOneDayLeftEmailJob($this->instance->id))->handle();
+
+        Mail::assertSent(AppInstanceOneDayLeftMail::class);
+
+        $this->assertTrue($this->instance->fresh()->one_day_left_email_sent);
+    }
+
+    public function test_flag_stays_false_when_send_throws(): void
+    {
+        // Force the synchronous send to fail so the job should throw before
+        // the sent flag is updated.
+        $pendingMail = Mockery::mock();
+        $pendingMail->shouldReceive('cc')->andReturnSelf();
+        $pendingMail->shouldReceive('send')
+            ->andThrow(new RuntimeException('SMTP failure'));
+
+        Mail::shouldReceive('to')->andReturn($pendingMail);
+
+        try {
+            (new ProcessOneDayLeftEmailJob($this->instance->id))->handle();
+            $this->fail('Expected the job to propagate the send exception.');
+        } catch (RuntimeException $e) {
+            $this->assertSame('SMTP failure', $e->getMessage());
+        }
+
+        $this->assertFalse(
+            $this->instance->fresh()->one_day_left_email_sent,
+            'The sent flag must remain false when delivery fails so the job can retry.'
+        );
+    }
+}