fix enrollment and registration email send

app/Services/EnrollmentRegistrationEmailService.php

@@ -11,6 +11,7 @@ use DateTimeInterface;
 final class EnrollmentRegistrationEmailService
 {
     public const TEMPLATE_VERSION = 'phase5_consolidated_v3';
+    private const SEND_DELAY_SECONDS = 2;
 
     public function __construct(
         private readonly BaseConnection $db,
@@ -50,7 +51,7 @@ final class EnrollmentRegistrationEmailService
         return $summary;
     }
 
-    public function sendForSchoolYear(array $schoolYear, ?string $testEmail = null, bool $dryRun = false, bool $force = false): array
+    public function sendForSchoolYear(array $schoolYear, ?string $testEmail = null, bool $dryRun = false, bool $force = false, bool $failedOnly = false): array
     {
         $summary = ['recipients' => 0, 'sent' => 0, 'failed' => 0, 'skipped' => 0, 'messages' => []];
         if (! $dryRun && empty($schoolYear['registration_launch_approved_at'])) {
@@ -65,12 +66,28 @@ final class EnrollmentRegistrationEmailService
             return $summary;
         }
 
+        $failedParentIds = $failedOnly ? $this->failedParentIdsForSchoolYear((string) $schoolYear['name']) : null;
+        if ($failedOnly && $failedParentIds === []) {
+            $summary['messages'][] = 'No failed registration emails found for ' . (string) ($schoolYear['name'] ?? '') . '.';
+            return $summary;
+        }
+
+        $sentAttempted = false;
         foreach ($families as $family) {
-            if ($testEmail === null && ! $force && $this->alreadySent((string) $schoolYear['name'], (int) $family['parent_user_id'])) {
+            if ($failedParentIds !== null && ! in_array((int) $family['parent_user_id'], $failedParentIds, true)) {
                 $summary['skipped']++;
                 continue;
             }
 
+            if ($failedParentIds === null && $testEmail === null && ! $force && $this->alreadySent((string) $schoolYear['name'], (int) $family['parent_user_id'])) {
+                $summary['skipped']++;
+                continue;
+            }
+
+            if ($sentAttempted && ! $dryRun) {
+                sleep(self::SEND_DELAY_SECONDS);
+            }
+
             $message = $this->buildMessage($schoolYear, $family);
             if ($testEmail !== null) {
                 $message['subject'] = '[TEST] ' . $message['subject'];
@@ -85,6 +102,8 @@ final class EnrollmentRegistrationEmailService
             if (! $dryRun && $recordId !== null) {
                 $this->recordDelivery($recordId, $sent, $sent ? null : 'Email send failed');
             }
+
+            $sentAttempted = true;
         }
 
         return $summary;
@@ -153,14 +172,14 @@ final class EnrollmentRegistrationEmailService
         return $examples;
     }
 
-    public function sendForSchoolYearName(string $schoolYearName, bool $force = false): array
+    public function sendForSchoolYearName(string $schoolYearName, bool $force = false, bool $failedOnly = false): array
     {
         $schoolYear = $this->schoolYearByName($schoolYearName);
         if ($schoolYear === null) {
             return ['recipients' => 0, 'sent' => 0, 'failed' => 0, 'skipped' => 1, 'messages' => ['School year was not found.']];
         }
 
-        return $this->sendForSchoolYear($schoolYear, null, false, $force);
+        return $this->sendForSchoolYear($schoolYear, null, false, $force, $failedOnly);
     }
 
     private function buildMessage(array $schoolYear, array $family): array
@@ -478,6 +497,39 @@ final class EnrollmentRegistrationEmailService
             ->countAllResults() > 0;
     }
 
+    /**
+     * @return list<int>
+     */
+    private function failedParentIdsForSchoolYear(string $schoolYear): array
+    {
+        if (! $this->db->tableExists('enrollment_email_records')) {
+            return [];
+        }
+
+        $rows = $this->db->table('enrollment_email_records')
+            ->select('parent_user_id, delivery_status')
+            ->where('school_year', $schoolYear)
+            ->orderBy('created_at', 'DESC')
+            ->orderBy('id', 'DESC')
+            ->get()
+            ->getResultArray();
+
+        $latestByParent = [];
+        foreach ($rows as $row) {
+            $parentId = (int) ($row['parent_user_id'] ?? 0);
+            if ($parentId <= 0 || array_key_exists($parentId, $latestByParent)) {
+                continue;
+            }
+
+            $latestByParent[$parentId] = (string) ($row['delivery_status'] ?? '');
+        }
+
+        return array_values(array_map(
+            'intval',
+            array_keys(array_filter($latestByParent, static fn (string $status): bool => $status === 'failed'))
+        ));
+    }
+
     private function latestEmailRecord(string $schoolYear, int $parentId): ?array
     {
         if (! $this->db->tableExists('enrollment_email_records')) {