diff --git a/app/Console/Commands/TestMail.php b/app/Console/Commands/TestEmail.php
similarity index 79%
rename from app/Console/Commands/TestMail.php
rename to app/Console/Commands/TestEmail.php
index b0b55ea..71ef4f0 100644
--- a/app/Console/Commands/TestMail.php
+++ b/app/Console/Commands/TestEmail.php
@@ -2,10 +2,11 @@
 
 namespace App\Console\Commands;
 
+use App\Files\TmpFile;
 use App\Logic\EmailManager;
-use App\Mail\Test;
+use App\Email\Test;
 
-class TestMail extends BaseCommand
+class TestEmail extends BaseCommand
 {
 
     const COMMAND = "mail:test {email}";
@@ -49,11 +50,17 @@ class TestMail extends BaseCommand
     {
         $email = $this->argument('email');
 
+        $file = new TmpFile();
+        $file->put("iwabuchi text");
+
+
         $mailer = new Test();
         $mailer->setEmail($email);
 
         $manager = new EmailManager($mailer);
-        $manager->confirm();
+        $manager
+            ->attach($file->getFullPath(), "test.txt", "text/plain")
+            ->confirm();
 
         return self::RESULTCODE_SUCCESS;
     }
diff --git a/app/Mail/BaseMailer.php b/app/Email/BaseEmailer.php
similarity index 83%
rename from app/Mail/BaseMailer.php
rename to app/Email/BaseEmailer.php
index 3ca9856..ed22a2f 100644
--- a/app/Mail/BaseMailer.php
+++ b/app/Email/BaseEmailer.php
@@ -1,18 +1,20 @@
 <?php
 
-namespace App\Mail;
+namespace App\Email;
 
 use App\Exceptions\AppCommonException;
 use App\Models\Email;
+use App\Models\EmailAttachment;
 use App\Models\User;
 use App\Util\DateUtil;
 use Illuminate\Bus\Queueable;
+use Illuminate\Database\Eloquent\Collection;
 use Illuminate\Mail\Mailable;
 use Illuminate\Queue\SerializesModels;
 use Illuminate\Support\Facades\Mail;
 use Illuminate\Support\Str;
 
-abstract class BaseMailer extends Mailable
+abstract class BaseEmailer extends Mailable
 {
     use Queueable, SerializesModels;
 
@@ -26,6 +28,11 @@ abstract class BaseMailer extends Mailable
     protected string|null $__contractId = null;
     protected string|null $__receiptIssuingOrderId = null;
 
+    /**
+     * 添付ファイル
+     * @var Collection<int, EmailAttachment>|null
+     */
+    protected ?Collection $__attachments = null;
 
     public function sendEmail(string $email)
     {
@@ -67,9 +74,25 @@ abstract class BaseMailer extends Mailable
 
     public function build()
     {
-        return $this->text($this->getTemplateName())
+        $this->text($this->getTemplateName())
             ->subject($this->getSubject())
             ->with($this->getParams());
+
+        // 添付ファイル処理
+        if ($this->__attachments !== null) {
+            $count = $this->__attachments->count();
+            foreach ($this->__attachments as $attachment) {
+                $filepath = $attachment->filepath;
+                $as = $attachment->send_filename;
+                $mime = $attachment->mime;
+                $this->attach($filepath, [
+                    'as' => $as,
+                    'mime' => $mime,
+                ]);
+            }
+        }
+
+        return $this;
     }
 
     public function setConfigDefault()
diff --git a/app/Mail/Guests/Guest.php b/app/Email/Guests/Guest.php
similarity index 64%
rename from app/Mail/Guests/Guest.php
rename to app/Email/Guests/Guest.php
index 104aecf..641411d 100644
--- a/app/Mail/Guests/Guest.php
+++ b/app/Email/Guests/Guest.php
@@ -1,10 +1,10 @@
 <?php
 
-namespace App\Mail\Guests;
+namespace App\Email\Guests;
 
-use App\Mail\BaseMailer;
+use App\Email\BaseEmailer;
 
-abstract class Guest extends BaseMailer
+abstract class Guest extends BaseEmailer
 {
     public function getParams(): array
     {
diff --git a/app/Email/Guests/ReceiptA4.php b/app/Email/Guests/ReceiptA4.php
new file mode 100644
index 0000000..15aa593
--- /dev/null
+++ b/app/Email/Guests/ReceiptA4.php
@@ -0,0 +1,38 @@
+<?php
+
+namespace App\Email\Guests;
+
+use App\Models\ReceiptIssuingOrder;
+use Illuminate\Support\Carbon;
+
+class ReceiptA4 extends Guest
+{
+
+    /**
+     * Create a new message instance.
+     *
+     * @return void
+     */
+    public function __construct(private ReceiptIssuingOrder $order)
+    {
+    }
+
+    public function getTemplateName(): string
+    {
+        return 'mails.guests.receipt_a4';
+    }
+
+    public function getSubject(): string
+    {
+        return '領収証の送付';
+    }
+
+    public function getGuestParams(): array
+    {
+        return [
+            'shopName' => $this->order->receipt_shop_name,
+            'useDate' => $this->order->receipt_use_date->format('Y/m/d'),
+            'amount' => number_format($this->order->receipt_amount),
+        ];
+    }
+}
diff --git a/app/Mail/Sender.php b/app/Email/Sender.php
similarity index 87%
rename from app/Mail/Sender.php
rename to app/Email/Sender.php
index 8ed84eb..3862fac 100644
--- a/app/Mail/Sender.php
+++ b/app/Email/Sender.php
@@ -1,8 +1,7 @@
 <?php
 
-namespace App\Mail;
+namespace App\Email;
 
-use App\Middlewares\Now;
 use App\Models\Email;
 use App\Util\DateUtil;
 use Exception;
@@ -24,7 +23,7 @@ class Sender
 
         try {
             Mail::to($email->email)
-                ->send(new TextMail($email->subject, $email->content));
+                ->send(new TextEmail($email->subject, $email->content, $email->emailAttachments));
         } catch (Exception $e) {
             Log::error("メール送信失敗", [
                 'id' => $email->id,
diff --git a/app/Mail/Test.php b/app/Email/Test.php
similarity index 83%
rename from app/Mail/Test.php
rename to app/Email/Test.php
index 9f0c1e0..149f114 100644
--- a/app/Mail/Test.php
+++ b/app/Email/Test.php
@@ -1,8 +1,8 @@
 <?php
 
-namespace App\Mail;
+namespace App\Email;
 
-class Test extends BaseMailer
+class Test extends BaseEmailer
 {
     public function getTemplateName(): string
     {
diff --git a/app/Mail/TextMail.php b/app/Email/TextEmail.php
similarity index 77%
rename from app/Mail/TextMail.php
rename to app/Email/TextEmail.php
index 2d07898..8165a18 100644
--- a/app/Mail/TextMail.php
+++ b/app/Email/TextEmail.php
@@ -1,21 +1,24 @@
 <?php
 
-namespace App\Mail;
+namespace App\Email;
 
 use Illuminate\Bus\Queueable;
+use Illuminate\Database\Eloquent\Collection;
 use Illuminate\Queue\SerializesModels;
 
-class TextMail extends BaseMailer
+class TextEmail extends BaseEmailer
 {
     use Queueable, SerializesModels;
 
     private string $__subject;
     private string $__contents;
 
-    public function __construct(string $subject, string $contents)
+
+    public function __construct(string $subject, string $contents, ?Collection $attachments = null)
     {
         $this->__subject = $subject;
         $this->__contents = $contents;
+        $this->__attachments = $attachments;
     }
 
     public function getTemplateName(): string
diff --git a/app/Events/Mail/ConfirmEvent.php b/app/Events/Email/ConfirmEvent.php
similarity index 50%
rename from app/Events/Mail/ConfirmEvent.php
rename to app/Events/Email/ConfirmEvent.php
index 715227b..81cb003 100644
--- a/app/Events/Mail/ConfirmEvent.php
+++ b/app/Events/Email/ConfirmEvent.php
@@ -1,10 +1,12 @@
 <?php
 
-namespace App\Events\Mail;
+namespace App\Events\Email;
 
-use App\Mail\BaseMailer;
+use App\Email\BaseEmailer;
 use App\Models\Email;
+use App\Models\EmailAttachment;
 use Illuminate\Broadcasting\InteractsWithSockets;
+use Illuminate\Database\Eloquent\Collection;
 use Illuminate\Foundation\Events\Dispatchable;
 use Illuminate\Queue\SerializesModels;
 
@@ -19,7 +21,7 @@ class ConfirmEvent
      *
      * @return void
      */
-    public function __construct(Email|BaseMailer $email)
+    public function __construct(Email|BaseEmailer $email, ?Collection $attachments = null)
     {
         if ($email instanceof Email) {
             $this->email = $email;
@@ -27,5 +29,14 @@ class ConfirmEvent
             $this->email = $email->makeModel();
             $this->email->save();
         }
+        if ($attachments !== null) {
+            foreach ($attachments as $attachment) {
+                if (!($attachment instanceof EmailAttachment)) continue;
+
+                $emailId = $this->email->id;
+                $attachment->email_id = $emailId;
+                $attachment->save();
+            }
+        }
     }
 }
diff --git a/app/Events/ReceiptIssuingOrder/EmailOrderEvent.php b/app/Events/ReceiptIssuingOrder/EmailOrderEvent.php
new file mode 100644
index 0000000..d8dfdd9
--- /dev/null
+++ b/app/Events/ReceiptIssuingOrder/EmailOrderEvent.php
@@ -0,0 +1,14 @@
+<?php
+
+namespace App\Events\ReceiptIssuingOrder;
+
+/**
+ * Email送付依頼イベント
+ */
+class EmailOrderEvent extends ReceiptIssuingOrderEvent
+{
+    public function getEventName(): string
+    {
+        return "Email送付依頼";
+    }
+}
diff --git a/app/Files/PDF/Receipt/A4Receipt.php b/app/Files/PDF/Receipt/A4Receipt.php
new file mode 100644
index 0000000..c5af09b
--- /dev/null
+++ b/app/Files/PDF/Receipt/A4Receipt.php
@@ -0,0 +1,27 @@
+<?php
+
+namespace App\Files\PDF\Receipt;
+
+use App\Files\TmpFile;
+
+class A4Receipt extends TmpFile
+{
+
+    protected const DIR = ['receipt_pdf'];
+
+    /**
+     * @override
+     */
+    protected function getFileTypeName(): string
+    {
+        return "A4Receipt";
+    }
+
+    /**
+     * @override
+     */
+    protected function getFileExtension(): string
+    {
+        return "pdf";
+    }
+}
diff --git a/app/Http/Controllers/Web/ReceiptIssuingOrder/EmailOrderController.php b/app/Http/Controllers/Web/ReceiptIssuingOrder/EmailOrderController.php
new file mode 100644
index 0000000..ce94d8c
--- /dev/null
+++ b/app/Http/Controllers/Web/ReceiptIssuingOrder/EmailOrderController.php
@@ -0,0 +1,54 @@
+<?php
+
+namespace App\Http\Controllers\Web\ReceiptIssuingOrder;
+
+use App\Http\Controllers\Web\IParam;
+use App\Http\Controllers\Web\WebController;
+use App\Logic\ReceiptIssuingOrder\Custom\HelloTechno\PDFDownLoadManagerHelloTechno;
+use App\Logic\ReceiptIssuingOrder\UpdateManager;
+use App\Models\ReceiptIssuingOrder;
+use App\Util\DateUtil;
+use Illuminate\Http\JsonResponse;
+use Illuminate\Http\Request;
+
+class EmailOrderController extends WebController
+{
+    public function name(): string
+    {
+        return "領収証Email送付依頼";
+    }
+
+    public function description(): string
+    {
+        return "領収証をEmail送付依頼を登録する";
+    }
+
+    public function __construct(
+        protected EmailOrderParam $param,
+        private UpdateManager $manager,
+        private PDFDownLoadManagerHelloTechno $pdf,
+    ) {
+        parent::__construct();
+    }
+
+    protected function getParam(): IParam
+    {
+        return $this->param;
+    }
+
+    protected function run(Request $request): JsonResponse
+    {
+        $param = $this->param;
+
+        $file = $this->pdf->initByToken($param->accessToken)
+            ->checkTimestamp($param->timestamp)
+            ->getA4File();
+
+        $this->manager->initByToken($param->accessToken)
+            ->checkTimestamp($param->timestamp)
+            ->emailOrder($param->email, $file)
+            ->update();
+
+        return $this->successResponse();
+    }
+}
diff --git a/app/Http/Controllers/Web/ReceiptIssuingOrder/EmailOrderParam.php b/app/Http/Controllers/Web/ReceiptIssuingOrder/EmailOrderParam.php
new file mode 100644
index 0000000..0e2f6b2
--- /dev/null
+++ b/app/Http/Controllers/Web/ReceiptIssuingOrder/EmailOrderParam.php
@@ -0,0 +1,27 @@
+<?php
+
+namespace App\Http\Controllers\Web\ReceiptIssuingOrder;
+
+use App\Http\Controllers\Web\BaseParam;
+use App\Http\Controllers\Web\Rule;
+use App\Http\Controllers\Web\TimestampParam;
+use App\Models\ReceiptIssuingOrder;
+
+/**
+ * @property string $accessToken
+ * @property string $email
+ */
+
+class EmailOrderParam extends BaseParam implements TimestampParam
+{
+    public function rules(): array
+    {
+        return array_merge(
+            [
+                ReceiptIssuingOrder::COL_NAME_ACCESS_TOKEN => $this->str(),
+                ReceiptIssuingOrder::COL_NAME_EMAIL => $this->str([...Rule::email()]),
+            ],
+            $this->timestamp(),
+        );
+    }
+}
diff --git a/app/Http/Controllers/Web/Rule.php b/app/Http/Controllers/Web/Rule.php
new file mode 100644
index 0000000..265f533
--- /dev/null
+++ b/app/Http/Controllers/Web/Rule.php
@@ -0,0 +1,14 @@
+<?php
+
+namespace App\Http\Controllers\Web;
+
+abstract class Rule
+{
+    public static function email(): array
+    {
+        $ret = [];
+        $ret[] = "email:strict,filter,dns";
+        $ret[] = "max:255";
+        return $ret;
+    }
+}
diff --git a/app/Jobs/Mail/SimpleMail.php b/app/Jobs/Email/SimpleEmail.php
similarity index 89%
rename from app/Jobs/Mail/SimpleMail.php
rename to app/Jobs/Email/SimpleEmail.php
index e7fd3cd..a4918d0 100644
--- a/app/Jobs/Mail/SimpleMail.php
+++ b/app/Jobs/Email/SimpleEmail.php
@@ -1,9 +1,9 @@
 <?php
 
-namespace App\Jobs\Mail;
+namespace App\Jobs\Email;
 
 use App\Codes\QueueName;
-use App\Mail\Sender;
+use App\Email\Sender;
 use App\Models\Email;
 use Illuminate\Bus\Queueable;
 use Illuminate\Contracts\Queue\ShouldQueue;
@@ -11,7 +11,7 @@ use Illuminate\Foundation\Bus\Dispatchable;
 use Illuminate\Queue\InteractsWithQueue;
 use Illuminate\Queue\SerializesModels;
 
-class SimpleMail implements ShouldQueue
+class SimpleEmail implements ShouldQueue
 {
     use Dispatchable, InteractsWithQueue, Queueable, SerializesModels;
 
diff --git a/app/Jobs/ReceiptIssuingOrder/PollEmailSendStatus.php b/app/Jobs/ReceiptIssuingOrder/PollEmailSendStatus.php
new file mode 100644
index 0000000..ce49b79
--- /dev/null
+++ b/app/Jobs/ReceiptIssuingOrder/PollEmailSendStatus.php
@@ -0,0 +1,78 @@
+<?php
+
+namespace App\Jobs\ReceiptIssuingOrder;
+
+use App\Codes\QueueName;
+use App\Models\Email;
+use App\Models\ReceiptIssuingOrder;
+use App\Util\DateUtil;
+use Illuminate\Bus\Queueable;
+use Illuminate\Contracts\Queue\ShouldQueue;
+use Illuminate\Foundation\Bus\Dispatchable;
+use Illuminate\Queue\InteractsWithQueue;
+use Illuminate\Queue\SerializesModels;
+use Illuminate\Support\Carbon;
+use Illuminate\Support\Facades\Log;
+
+class PollEmailSendStatus implements ShouldQueue
+{
+    use Dispatchable, InteractsWithQueue, Queueable, SerializesModels;
+
+    private int $currentRetryCount;
+
+    /**
+     * Create a new job instance.
+     *
+     * @return void
+     */
+    public function __construct(
+        private ReceiptIssuingOrder $order,
+    ) {
+        $this->onQueue(QueueName::JOB->value);
+    }
+
+    /**
+     * Execute the job.
+     *
+     * @return void
+     */
+    public function handle()
+    {
+        info("領収証Emailポーリング:" . $this->order->receipt_pdf_email_id);
+
+        $email = Email::findOrFail($this->order->receipt_pdf_email_id);
+        $sendDatetime = $email->send_datetime;
+
+        if ($email->send_datetime !== null) {
+            // ポーリング終了
+            $this->donePolling($sendDatetime);
+        } else if ($email->is_failed) {
+            // ポーリング終了
+            $this->donePolling($sendDatetime);
+        } else {
+            $limit = $this->order->status_receipt_email_send_order_datetime->clone()->addDays(3);
+            if (DateUtil::now()->gt($limit)) {
+                // ポーリング終了(未完了)
+                $this->donePolling($sendDatetime);
+                Log::warning("領収証Email送信未完了検知 OrderID:%s", $this->order->id);
+            } else {
+                // ポーリング継続
+                $this->continuePolling();
+            }
+        }
+    }
+
+    private function donePolling(Carbon $sendDatetime)
+    {
+        $this->order->status_receipt_email_send_datetime  = $sendDatetime;
+        $this->order->save();
+        info("領収証Emailポーリング完了:" . $this->order->receipt_pdf_email_id);
+    }
+
+    private function continuePolling()
+    {
+        static::dispatch($this->order)
+            ->delay(DateUtil::now()->addMinutes(5));
+        info("領収証Emailポーリング継続:" . $this->order->receipt_pdf_email_id);
+    }
+}
diff --git a/app/Listeners/Mail/MailSendJobRegister.php b/app/Listeners/Email/EmailSendJobRegister.php
similarity index 75%
rename from app/Listeners/Mail/MailSendJobRegister.php
rename to app/Listeners/Email/EmailSendJobRegister.php
index 0f8f10c..8ede54c 100644
--- a/app/Listeners/Mail/MailSendJobRegister.php
+++ b/app/Listeners/Email/EmailSendJobRegister.php
@@ -1,12 +1,12 @@
 <?php
 
-namespace App\Listeners\Mail;
+namespace App\Listeners\Email;
 
-use App\Events\Mail\ConfirmEvent;
-use App\Jobs\Mail\SimpleMail;
+use App\Events\Email\ConfirmEvent;
+use App\Jobs\Email\SimpleEmail;
 use App\Util\DateUtil;
 
-class MailSendJobRegister
+class EmailSendJobRegister
 {
 
     /**
@@ -30,7 +30,8 @@ class MailSendJobRegister
 
             $email->confirm_datetime = DateUtil::now();
             $email->save();
-            SimpleMail::dispatch($event->email);
+
+            SimpleEmail::dispatch($event->email);
         }
     }
 }
diff --git a/app/Logic/EmailManager.php b/app/Logic/EmailManager.php
index e3b9329..060c407 100644
--- a/app/Logic/EmailManager.php
+++ b/app/Logic/EmailManager.php
@@ -2,11 +2,13 @@
 
 namespace App\Logic;
 
-use App\Events\Mail\ConfirmEvent;
+use App\Events\Email\ConfirmEvent;
 use App\Exceptions\AppCommonException;
-use App\Mail\BaseMailer;
+use App\Email\BaseEmailer;
 use App\Models\Email;
+use App\Models\EmailAttachment;
 use Exception;
+use Illuminate\Database\Eloquent\Collection;
 use Illuminate\Support\Carbon;
 use Validator;
 
@@ -17,13 +19,18 @@ class EmailManager
 
     private bool $canSend = false;
 
-    public function __construct(int|BaseMailer $param)
+    /**
+     * @var Collection<int, EmailAttachment>|null
+     */
+    private ?Collection $attachments = null;
+
+    public function __construct(int|BaseEmailer $param)
     {
         if (is_numeric($param)) {
             $this->model = Email::lockForUpdate()->findOrfail($param);
             $this->canSend = $this->model->send_datetime === null;
             if (!$this->checkAuth()) throw new AppCommonException("メール権限エラー");
-        } else if ($param instanceof BaseMailer) {
+        } else if ($param instanceof BaseEmailer) {
             $this->model = $param->makeModel();
         }
     }
@@ -35,6 +42,7 @@ class EmailManager
 
     public function getEmailId()
     {
+        $this->model->setId();
         return $this->model->id;
     }
 
@@ -70,6 +78,22 @@ class EmailManager
         return $this;
     }
 
+    public function attach(string $filepath, string $filename, string $mimeType)
+    {
+
+        if ($this->attachments === null) {
+            $this->attachments = new Collection();
+        }
+        $attachment = new EmailAttachment();
+        $attachment->filepath = $filepath;
+        $attachment->send_filename = $filename;
+        $attachment->mime = $mimeType;
+
+        $this->attachments->push($attachment);
+
+        return $this;
+    }
+
     public function update()
     {
         $this->model->save();
@@ -88,7 +112,8 @@ class EmailManager
         }
 
         if ($this->canSend() !== null) {
-            ConfirmEvent::dispatch($this->model);
+            $this->model->setId();
+            ConfirmEvent::dispatch($this->model, $this->attachments);
         } else {
             throw new AppCommonException("送信済みエラー");
         }
diff --git a/app/Logic/ReceiptIssuingOrder/PDFDownLoadManager.php b/app/Logic/ReceiptIssuingOrder/PDFDownLoadManager.php
index 7ad3132..dc13f23 100644
--- a/app/Logic/ReceiptIssuingOrder/PDFDownLoadManager.php
+++ b/app/Logic/ReceiptIssuingOrder/PDFDownLoadManager.php
@@ -5,9 +5,12 @@ namespace App\Logic\ReceiptIssuingOrder;
 use App\Codes\PrefCode;
 use App\Events\ReceiptIssuingOrder\DownloadedEvent;
 use App\Exceptions\AppCommonException;
+use App\Files\PDF\Receipt\A4Receipt;
+use App\Files\TmpFile;
 use App\Models\ReceiptIssuingOrder;
 use App\Models\ReceiptIssuingOrderTax;
 use App\Util\DateUtil;
+use Barryvdh\Snappy\PdfWrapper;
 use PDF;
 
 class PDFDownLoadManager extends ReceiptIssuingOrderManager
@@ -25,13 +28,7 @@ class PDFDownLoadManager extends ReceiptIssuingOrderManager
     {
         $order = $this->order;
 
-        $data =  $this->getPDFData();
-
-
-        $pdf = PDF::loadView('pdf/receipt_a4', $data);
-        // はがきサイズを指定
-        $ret = $pdf->setPaper('A4')
-            ->setOption('encoding', 'utf-8')
+        $ret = $this->makeA4()
             ->inline();
         if ($order->status_receipt_download_datetime === null) {
 
@@ -44,6 +41,30 @@ class PDFDownLoadManager extends ReceiptIssuingOrderManager
 
         return $ret;
     }
+
+    public function getA4File(): A4Receipt
+    {
+        $ret = $this->makeA4()
+            ->output();
+
+        $file = new A4Receipt();
+        $file->put($ret);
+
+        return $file;
+    }
+
+    protected function makeA4(): PdfWrapper
+    {
+        $data =  $this->getPDFData();
+
+        $pdf = PDF::loadView('pdf/receipt_a4', $data);
+        // はがきサイズを指定
+        $ret = $pdf->setPaper('A4')
+            ->setOption('encoding', 'utf-8');
+
+        return $ret;
+    }
+
     public function downlaodLetter()
     {
         $data =  $this->getPDFData();
diff --git a/app/Logic/ReceiptIssuingOrder/UpdateManager.php b/app/Logic/ReceiptIssuingOrder/UpdateManager.php
index b63a160..5fc03b7 100644
--- a/app/Logic/ReceiptIssuingOrder/UpdateManager.php
+++ b/app/Logic/ReceiptIssuingOrder/UpdateManager.php
@@ -2,11 +2,16 @@
 
 namespace App\Logic\ReceiptIssuingOrder;
 
+use App\Email\Guests\ReceiptA4;
 use App\Events\ReceiptIssuingOrder\ChangeHandlerEvent;
 use App\Events\ReceiptIssuingOrder\ConfirmedEvent;
+use App\Events\ReceiptIssuingOrder\EmailOrderEvent;
 use App\Events\ReceiptIssuingOrder\MailOrderEvent;
 use App\Events\ReceiptIssuingOrder\MailPostedEvent;
 use App\Exceptions\AppCommonException;
+use App\Files\PDF\Receipt\A4Receipt;
+use App\Jobs\ReceiptIssuingOrder\PollEmailSendStatus;
+use App\Logic\EmailManager;
 use App\Logic\SMS\SMSManager;
 use App\Models\ReceiptIssuingOrder;
 use App\Models\User;
@@ -71,6 +76,43 @@ class UpdateManager extends ReceiptIssuingOrderManager
         return $this;
     }
 
+    /**
+     * 郵送投函完了
+     *
+     * @param array $attr
+     * @return static
+     */
+    public function emailOrder(string $email, A4Receipt $file, array $attr = []): static
+    {
+        $this->fill([
+            ReceiptIssuingOrder::COL_NAME_EMAIL => $email,
+            ReceiptIssuingOrder::COL_NAME_STATUS_RECEIPT_EMAIL_SEND_ORDER_DATETIME => DateUtil::now(),
+            ...$attr,
+        ]);
+
+        // メール送信
+        $mail = new ReceiptA4($this->order);
+        $mail->setEmail($this->order->email);
+        $manager = new EmailManager($mail);
+
+        $filename = sprintf("領収証_%s.pdf", $this->order->receipt_no);
+
+        $manager->attach($file->getFullPath(), $filename, "application/pdf")
+            ->confirm();
+
+
+        $this->fill([
+            ReceiptIssuingOrder::COL_NAME_RECEIPT_PDF_EMAIL_ID => $manager->getEmailId()
+        ]);
+
+
+        // イベント登録
+        EmailOrderEvent::dispatch($this->order);
+        PollEmailSendStatus::dispatch($this->order);
+
+        return $this;
+    }
+
     /**
      * 領収証確定
      *
diff --git a/app/Mail/Admins/Admin.php b/app/Mail/Admins/Admin.php
deleted file mode 100644
index ca51c23..0000000
--- a/app/Mail/Admins/Admin.php
+++ /dev/null
@@ -1,15 +0,0 @@
-<?php
-
-namespace App\Mail\Admins;
-
-use App\Mail\BaseMailer;
-
-abstract class Admin extends BaseMailer
-{
-    public function getParams(): array
-    {
-        return array_merge($this->getAdminParams(), []);
-    }
-
-    abstract public function getAdminParams(): array;
-}
diff --git a/app/Mail/Admins/Ask.php b/app/Mail/Admins/Ask.php
deleted file mode 100644
index ceb15f1..0000000
--- a/app/Mail/Admins/Ask.php
+++ /dev/null
@@ -1,92 +0,0 @@
-<?php
-
-namespace App\Mail\Admins;
-
-use App\Models\Parking;
-use App\Models\SeasonTicketContract;
-use App\Models\SeasonTicketContractSubscription;
-use App\Models\User;
-use App\Models\UserDetail;
-use Illuminate\Support\Carbon;
-
-class Ask extends Admin
-{
-
-    protected string $askSubject;
-    protected string $askContents;
-    protected string|null $parkName = null;
-    protected string|null $userName;
-    protected string|null $userEmail;
-    protected int|null $seasonTicketSeqNo = null;
-    protected Carbon|null $subscribeDatetime = null;
-
-
-    public function __construct(
-        array $data,
-        User|null $user = null,
-        UserDetail|null $userDetail = null,
-        SeasonTicketContract|null $seasonTicketContract = null,
-        SeasonTicketContractSubscription|null $subscription = null,
-        Parking|null $parking = null,
-    ) {
-        $this->setValues($data);
-        if ($seasonTicketContract) {
-            $this->seasonTicketSeqNo = $seasonTicketContract->season_ticket_seq_no;
-        }
-        if ($subscription) {
-            $this->subscribeDatetime = $subscription->subscribe_datetime;
-        }
-        if ($user) {
-            $this->userEmail  = $user->email;
-        }
-        if ($userDetail) {
-            $this->userName  = sprintf(
-                "%s %s",
-                $userDetail->first_name,
-                $userDetail->last_name
-            );
-        }
-        if ($parking) {
-            $this->parkName = $parking->park_name;
-        }
-    }
-
-    public function getTemplateName(): string
-    {
-        return 'mails.admins.ask';
-    }
-
-    public function getSubject(): string
-    {
-        return sprintf(
-            '【スマートパーキングパス】【問い合わせ】【%s】%s',
-            $this->userName,
-            $this->askSubject
-        );
-    }
-
-    private function memberRegistration(): string
-    {
-        if ($this->seasonTicketSeqNo !== null || $this->subscribeDatetime !== null) {
-            return "あり";
-        }
-        return "なし";
-    }
-
-    public function getAdminParams(): array
-    {
-        return [
-            'askSubject' => $this->askSubject,
-            'askContents' => $this->askContents,
-
-            'parkName' => $this->parkName,
-            'userName' => $this->userName,
-            'userEmail' => $this->userEmail,
-
-            'seasonTicketSeqNo' => $this->seasonTicketSeqNo,
-            'subscribeDatetime' => $this->subscribeDatetime ? $this->subscribeDatetime->format('Y/m/d H:i:s') : null,
-
-            'memberRegistration' => $this->memberRegistration(),
-        ];
-    }
-}
diff --git a/app/Mail/Common/AskConfirmation.php b/app/Mail/Common/AskConfirmation.php
deleted file mode 100644
index bd7cb55..0000000
--- a/app/Mail/Common/AskConfirmation.php
+++ /dev/null
@@ -1,70 +0,0 @@
-<?php
-
-namespace App\Mail\Common;
-
-use App\Models\Parking;
-use App\Models\User;
-use App\Models\UserDetail;
-use Illuminate\Support\Carbon;
-
-trait AskConfirmation
-{
-
-    protected string $askSubject;
-    protected string $askContents;
-    protected string|null $parkName = null;
-    protected string|null $userName;
-    protected string|null $userEmail;
-    protected int|null $seasonTicketSeqNo = null;
-    protected Carbon|null $subscribeDatetime = null;
-
-    private bool $forMember = false;
-
-    abstract protected function setValues(\stdClass|array $data);
-
-    protected function setAskConfirmationData(
-        array $data,
-        User|null $user = null,
-        UserDetail|null $userDetail = null,
-        Parking|null $parking = null,
-    ) {
-        $this->setValues($data);
-        if ($user) {
-            $this->userEmail  = $user->email;
-            $this->forMember = true;
-        }
-        if ($userDetail) {
-            $this->userName  = sprintf(
-                "%s %s",
-                $userDetail->first_name,
-                $userDetail->last_name
-            );
-            $this->forMember = true;
-        }
-        if ($parking) {
-            $this->parkName = $parking->park_name;
-        }
-    }
-
-    public function getTemplateName(): string
-    {
-        return  $this->forMember ? 'mails.members.ask_confirmation' : 'mails.guests.ask_confirmation';
-    }
-
-    public function getSubject(): string
-    {
-        return '【スマートパーキングパス】お問い合わせ内容の確認';
-    }
-
-    protected function getAskConfirmationParams(): array
-    {
-        return [
-            'askSubject' => $this->askSubject,
-            'askContents' => $this->askContents,
-
-            'parkName' => $this->parkName,
-            'userName' => $this->userName,
-            'userEmail' => $this->userEmail,
-        ];
-    }
-}
diff --git a/app/Mail/Guests/AskConfirmation.php b/app/Mail/Guests/AskConfirmation.php
deleted file mode 100644
index af804be..0000000
--- a/app/Mail/Guests/AskConfirmation.php
+++ /dev/null
@@ -1,27 +0,0 @@
-<?php
-
-namespace App\Mail\Guests;
-
-use App\Mail\Common\AskConfirmation as CommonAskConfirmation;
-use App\Models\Parking;
-use App\Models\User;
-use App\Models\UserDetail;
-
-class AskConfirmation extends Guest
-{
-    use CommonAskConfirmation;
-
-    public function __construct(
-        array $data,
-        User|null $user = null,
-        UserDetail|null $userDetail = null,
-        Parking|null $parking = null,
-    ) {
-        $this->setAskConfirmationData($data, $user, $userDetail, $parking);
-    }
-
-    public function getGuestParams(): array
-    {
-        return $this->getAskConfirmationParams();
-    }
-}
diff --git a/app/Mail/Guests/ChangeEmailStart.php b/app/Mail/Guests/ChangeEmailStart.php
deleted file mode 100644
index c562030..0000000
--- a/app/Mail/Guests/ChangeEmailStart.php
+++ /dev/null
@@ -1,63 +0,0 @@
-<?php
-
-namespace App\Mail\Guests;
-
-use App\Models\ChangeEmail;
-use Exception;
-use Illuminate\Support\Carbon;
-
-class ChangeEmailStart extends Guest
-{
-
-    protected string $token;
-    protected Carbon $expiresAt;
-
-    protected $casts = [
-        'expiresAt' => 'datetime',
-    ];
-
-    /**
-     * Create a new message instance.
-     *
-     * @return void
-     */
-    public function __construct(ChangeEmail $model)
-    {
-        logger($model->toArray());
-        $this->setValues($model->toArray());
-    }
-
-    public function getTemplateName(): string
-    {
-        return 'mails.guests.change_email_start';
-    }
-
-    public function getSubject(): string
-    {
-        return '【スマートパーキングパス】Email変更手続きのご案内';
-    }
-
-    public function getGuestParams(): array
-    {
-        return [
-            'url' => $this->getUrl(),
-            'expiresAt' => $this->getExpiresAt(),
-        ];
-    }
-
-    private function getUrl()
-    {
-        return implode(
-            "/",
-            [
-                config("app.url"),
-                'change-email',
-                $this->token
-            ]
-        );
-    }
-    private function getExpiresAt()
-    {
-        return $this->expiresAt->format('Y/m/d H:i');
-    }
-}
diff --git a/app/Mail/Guests/EmailVerify.php b/app/Mail/Guests/EmailVerify.php
deleted file mode 100644
index 4b64333..0000000
--- a/app/Mail/Guests/EmailVerify.php
+++ /dev/null
@@ -1,65 +0,0 @@
-<?php
-
-namespace App\Mail\Guests;
-
-use App\Models\EmailVerify as ModelsEmailVerify;
-use Exception;
-use Illuminate\Support\Carbon;
-
-class EmailVerify extends Guest
-{
-    protected string $token;
-    protected Carbon $expiresAt;
-
-    protected $casts = [
-        'expiresAt' => 'datetime',
-    ];
-
-    /**
-     * Create a new message instance.
-     *
-     * @return void
-     */
-    public function __construct(ModelsEmailVerify $model)
-    {
-        $this->setValues($model->toArray());
-    }
-
-    public function getTemplateName(): string
-    {
-        return 'mails.guests.email_verify';
-    }
-
-    public function getSubject(): string
-    {
-        return '【スマートパーキングパス】会員登録のご案内';
-    }
-
-    public function getGuestParams(): array
-    {
-        return [
-            'url' => $this->getUrl(),
-            'expiresAt' => $this->getExpiresAt(),
-        ];
-    }
-
-    private function getUrl()
-    {
-        return implode(
-            "/",
-            [
-                config("app.url"),
-                'register/user',
-                $this->token
-            ]
-        );
-    }
-    private function getExpiresAt()
-    {
-        $date = $this->expiresAt;
-        if ($date !== null) {
-            return $date->format('Y/m/d H:i');
-        }
-        throw new Exception("有効期限日付不正");
-    }
-}
diff --git a/app/Mail/Members/AskConfirmation.php b/app/Mail/Members/AskConfirmation.php
deleted file mode 100644
index f16ccce..0000000
--- a/app/Mail/Members/AskConfirmation.php
+++ /dev/null
@@ -1,27 +0,0 @@
-<?php
-
-namespace App\Mail\Members;
-
-use App\Mail\Common\AskConfirmation as CommonAskConfirmation;
-use App\Models\Parking;
-use App\Models\User;
-use App\Models\UserDetail;
-
-class AskConfirmation  extends Member
-{
-    use CommonAskConfirmation;
-
-    public function __construct(
-        array $data,
-        User|null $user = null,
-        UserDetail|null $userDetail = null,
-        Parking|null $parking = null,
-    ) {
-        $this->setAskConfirmationData($data, $user, $userDetail, $parking);
-    }
-
-    public function getMemberParams(): array
-    {
-        return $this->getAskConfirmationParams();
-    }
-}
diff --git a/app/Mail/Members/AutoCancelSeasonTicketContract.php b/app/Mail/Members/AutoCancelSeasonTicketContract.php
deleted file mode 100644
index 5c3e504..0000000
--- a/app/Mail/Members/AutoCancelSeasonTicketContract.php
+++ /dev/null
@@ -1,42 +0,0 @@
-<?php
-
-namespace App\Mail\Members;
-
-use App\Models\SeasonTicketContract;
-use App\Models\Parking;
-
-class AutoCancelSeasonTicketContract extends Member
-{
-
-    protected string $parkName;
-    protected int $seasonTicketSeqNo;
-
-    /**
-     * Create a new message instance.
-     *
-     * @return void
-     */
-    public function __construct(Parking $parking, SeasonTicketContract $seasonTicketContract)
-    {
-        $this->setValues($parking->toArray());
-        $this->setValues($seasonTicketContract->toArray());
-    }
-
-    public function getTemplateName(): string
-    {
-        return 'mails.members.auto_cancel_season_ticket_contract';
-    }
-
-    public function getSubject(): string
-    {
-        return '【スマートパーキングパス】駐車場利用停止のお知らせ';
-    }
-
-    public function getMemberParams(): array
-    {
-        return [
-            'parkName' => $this->parkName,
-            'seasonTicketSeqNo' => $this->seasonTicketSeqNo,
-        ];
-    }
-}
diff --git a/app/Mail/Members/Bulk.php b/app/Mail/Members/Bulk.php
deleted file mode 100644
index e777f0e..0000000
--- a/app/Mail/Members/Bulk.php
+++ /dev/null
@@ -1,37 +0,0 @@
-<?php
-
-namespace App\Mail\Members;
-
-use Illuminate\Bus\Queueable;
-use Illuminate\Queue\SerializesModels;
-
-class Bulk extends Member
-{
-    use Queueable, SerializesModels;
-
-    private string $__subject;
-    private string $__contents;
-
-    public function __construct(string $subject, string $contents)
-    {
-        $this->__subject = $subject;
-        $this->__contents = $contents;
-    }
-
-    public function getTemplateName(): string
-    {
-        return 'mails.members.bulk';
-    }
-
-    public function getSubject(): string
-    {
-        return $this->__subject;
-    }
-
-    public function getMemberParams(): array
-    {
-        return [
-            'contents' => $this->__contents,
-        ];
-    }
-}
diff --git a/app/Mail/Members/Member.php b/app/Mail/Members/Member.php
deleted file mode 100644
index 0499d13..0000000
--- a/app/Mail/Members/Member.php
+++ /dev/null
@@ -1,17 +0,0 @@
-<?php
-
-namespace App\Mail\Members;
-
-use App\Mail\BaseMailer;
-
-abstract class Member extends BaseMailer
-{
-    public function getParams(): array
-    {
-        return array_merge($this->getMemberParams(), [
-            'email' => $this->__email
-        ]);
-    }
-
-    abstract public function getMemberParams(): array;
-}
diff --git a/app/Mail/Members/ResetIDm.php b/app/Mail/Members/ResetIDm.php
deleted file mode 100644
index acdc6c1..0000000
--- a/app/Mail/Members/ResetIDm.php
+++ /dev/null
@@ -1,42 +0,0 @@
-<?php
-
-namespace App\Mail\Members;
-
-use App\Exceptions\AppCommonException;
-
-class ResetIDm extends Member
-{
-    private string $confirmationCode;
-    private int $seasonTicketSeqNo;
-
-    public function __construct()
-    {
-        $context = $this->context();
-
-        $seasonTicketContract = $context->getSeasonTicketContract();
-        if ($seasonTicketContract === null) {
-            throw new AppCommonException("コンテキスト不正 定期契約情報");
-        }
-
-        $this->confirmationCode = $seasonTicketContract->confirmation_code;
-        $this->seasonTicketSeqNo = $seasonTicketContract->season_ticket_seq_no;
-    }
-
-    public function getTemplateName(): string
-    {
-        return 'mails.members.reset_idm';
-    }
-
-    public function getSubject(): string
-    {
-        return '【スマートパーキングパス】ICカードリセットのお知らせ';
-    }
-
-    public function getMemberParams(): array
-    {
-        return [
-            'confirmationCode' => $this->confirmationCode,
-            'seasonTicketSeqNo' => $this->seasonTicketSeqNo,
-        ];
-    }
-}
diff --git a/app/Mail/Members/ResetPasswordStart.php b/app/Mail/Members/ResetPasswordStart.php
deleted file mode 100644
index 094e1be..0000000
--- a/app/Mail/Members/ResetPasswordStart.php
+++ /dev/null
@@ -1,61 +0,0 @@
-<?php
-
-namespace App\Mail\Members;
-
-use App\Models\ResetPassword;
-use Illuminate\Support\Carbon;
-
-class ResetPasswordStart extends Member
-{
-
-    protected string $token;
-    protected Carbon $expiresAt;
-
-    protected $casts = [
-        'expiresAt' => 'datetime',
-    ];
-
-    /**
-     * Create a new message instance.
-     *
-     * @return void
-     */
-    public function __construct(ResetPassword $model)
-    {
-        $this->setValues($model->toArray());
-    }
-
-    public function getTemplateName(): string
-    {
-        return 'mails.members.reset_password_start';
-    }
-
-    public function getSubject(): string
-    {
-        return '【スマートパーキングパス】パスワードリセット手続きのご案内';
-    }
-
-    public function getMemberParams(): array
-    {
-        return [
-            'url' => $this->getUrl(),
-            'expiresAt' => $this->getExpiresAt(),
-        ];
-    }
-
-    private function getUrl()
-    {
-        return implode(
-            "/",
-            [
-                config("app.url"),
-                'password-reset',
-                $this->token
-            ]
-        );
-    }
-    private function getExpiresAt()
-    {
-        return $this->expiresAt->format('Y/m/d H:i');
-    }
-}
diff --git a/app/Mail/Members/SeasonTicketContractExpireRemind.php b/app/Mail/Members/SeasonTicketContractExpireRemind.php
deleted file mode 100644
index 14de7f2..0000000
--- a/app/Mail/Members/SeasonTicketContractExpireRemind.php
+++ /dev/null
@@ -1,45 +0,0 @@
-<?php
-
-namespace App\Mail\Members;
-
-use Illuminate\Support\Carbon;
-
-class SeasonTicketContractExpireRemind extends Member
-{
-    protected string|null $parkName;
-    protected int $seasonTicketSeqNo;
-    protected Carbon $expirationEndDate;
-
-    protected $casts = [
-        'expirationEndDate' => 'datetime',
-    ];
-
-    /**
-     * Create a new message instance.
-     *
-     * @return void
-     */
-    public function __construct(\stdClass $data)
-    {
-        $this->setValues($data);
-    }
-
-    public function getTemplateName(): string
-    {
-        return 'mails.members.season_ticket_contract_expires_remind';
-    }
-
-    public function getSubject(): string
-    {
-        return '【スマートパーキングパス】定期期限切れ予告通知';
-    }
-
-    public function getMemberParams(): array
-    {
-        return [
-            'parkName' => $this->parkName,
-            'seasonTicketSeqNo' => $this->seasonTicketSeqNo,
-            'expirationEndDate' => $this->expirationEndDate,
-        ];
-    }
-}
diff --git a/app/Mail/Members/Subscription/Approve.php b/app/Mail/Members/Subscription/Approve.php
deleted file mode 100644
index e4a4c7b..0000000
--- a/app/Mail/Members/Subscription/Approve.php
+++ /dev/null
@@ -1,111 +0,0 @@
-<?php
-
-namespace App\Mail\Members\Subscription;
-
-use App\Codes\ParkingUseTypeCode;
-use App\Codes\VehicleTypeCode;
-use App\Mail\Members\Member;
-use App\Models\Parking;
-use App\Models\SeasonTicketContract;
-use App\Models\SeasonTicketContractSubscription;
-use App\Models\User;
-use Illuminate\Support\Carbon;
-use LogicException;
-
-class Approve extends Member
-{
-    private string $email;
-    private string $parkName;
-    private Carbon|null $useStartRequestDate;
-    private VehicleTypeCode $vehicleType;
-    private string $contractorTypeName;
-    private int $seasonTicketSeqNo;
-    private int|null $confirmationCode;
-    private ParkingUseTypeCode $parkingUseType;
-
-    private string $customerCode;
-    private string $parkingManagementCode;
-
-
-    /**
-     * Create a new message instance.
-     *
-     * @return void
-     */
-    public function __construct(
-        User $user,
-        SeasonTicketContractSubscription|null $subscription,
-        Parking $parking,
-        SeasonTicketContract $seasonTicketContract,
-        string $contractorTypeName
-    ) {
-        $this->email = $user->email;
-        $this->parkName = $parking->park_name;
-        $this->useStartRequestDate = $subscription ? $subscription->use_start_request_date : null;
-        $this->vehicleType = $seasonTicketContract->vehicle_type;
-        $this->contractorTypeName = $contractorTypeName;
-        $this->seasonTicketSeqNo = $seasonTicketContract->season_ticket_seq_no;
-        $this->confirmationCode = $seasonTicketContract->confirmation_code;
-        $this->parkingUseType = $seasonTicketContract->parking_use_type;
-
-        $this->customerCode = $seasonTicketContract->customer_code;
-        $this->parkingManagementCode = $seasonTicketContract->parking_management_code;
-    }
-
-    public function getTemplateName(): string
-    {
-        return 'mails.members.subscription.approve';
-    }
-
-    public function getSubject(): string
-    {
-        return '【スマートパーキングパス】定期申し込み完了';
-    }
-
-    public function getMemberParams(): array
-    {
-        return [
-            'email' => $this->email,
-            'park_name' => $this->parkName,
-            'use_start_request_date' => $this->getUseStartRequestDate(),
-            'vehicle_type' => $this->getVehicleType(),
-            'contractor_type_name' => $this->contractorTypeName,
-            'how_to_use' => $this->getHowToUse(),
-            'season_ticket_seq_no' => $this->seasonTicketSeqNo,
-            'confirmation_code' => $this->confirmationCode,
-            'ic_card_rental_request' => $this->parkingUseType === ParkingUseTypeCode::IC_RENTAL,
-            'ic_self_card_request' => $this->parkingUseType === ParkingUseTypeCode::IC_SELF,
-            'ic_qr_code_request' => $this->parkingUseType === ParkingUseTypeCode::QR,
-            'my_qr_code_url' => $this->getMyQrCodeUrl(),
-        ];
-    }
-
-    private function getUseStartRequestDate()
-    {
-        if ($this->useStartRequestDate === null) return "-";
-        return $this->useStartRequestDate->format("Y年m月d日");
-    }
-
-    private function getVehicleType()
-    {
-        return VehicleTypeCode::getName($this->vehicleType);
-    }
-
-    private function getHowToUse()
-    {
-        switch ($this->parkingUseType) {
-            case ParkingUseTypeCode::IC_RENTAL:
-                return "貸与ICカード";
-            case ParkingUseTypeCode::IC_SELF:
-                return "個人ICカード";
-            case ParkingUseTypeCode::QR:
-                return "QRコード";
-        }
-        throw new LogicException(sprintf("不適切な駐車場利用方法 %d", $this->parkingUseType->value));
-    }
-
-    private function getMyQrCodeUrl()
-    {
-        return $this->getAppUrl(['app', 'qrcode', 'detail', $this->customerCode, $this->parkingManagementCode]);
-    }
-}
diff --git a/app/Mail/Members/Subscription/Cancel.php b/app/Mail/Members/Subscription/Cancel.php
deleted file mode 100644
index eb033d7..0000000
--- a/app/Mail/Members/Subscription/Cancel.php
+++ /dev/null
@@ -1,45 +0,0 @@
-<?php
-
-namespace App\Mail\Members\Subscription;
-
-use App\Exceptions\AppCommonException;
-use App\Mail\Members\Member;
-
-class Cancel extends Member
-{
-
-    private string $parkName;
-
-    /**
-     * Create a new message instance.
-     *
-     * @return void
-     */
-    public function __construct()
-    {
-        $context = $this->context();
-        $parking = $context->getParking();
-        if ($parking === null) {
-            throw new AppCommonException("コンテキスト不正 駐車場情報");
-        }
-
-        $this->parkName = $parking->park_name;
-    }
-
-    public function getTemplateName(): string
-    {
-        return 'mails.members.subscription.cancel';
-    }
-
-    public function getSubject(): string
-    {
-        return '【スマートパーキングパス】申込キャンセルのお知らせ';
-    }
-
-    public function getMemberParams(): array
-    {
-        return [
-            'parkName' => $this->parkName,
-        ];
-    }
-}
diff --git a/app/Mail/Members/Subscription/Entry.php b/app/Mail/Members/Subscription/Entry.php
deleted file mode 100644
index c078344..0000000
--- a/app/Mail/Members/Subscription/Entry.php
+++ /dev/null
@@ -1,70 +0,0 @@
-<?php
-
-namespace App\Mail\Members\Subscription;
-
-use App\Exceptions\AppCommonException;
-use App\Mail\Members\Member;
-use Illuminate\Support\Carbon;
-
-class Entry extends Member
-{
-
-    private string $email;
-    private string $parkName;
-    private Carbon|null $useStartRequestDate;
-    private string $memo;
-    /**
-     * Create a new message instance.
-     *
-     * @return void
-     */
-    public function __construct()
-    {
-        $context = $this->context();
-
-        $user = $context->getUser();
-        $subscription = $context->getSeasonTicketContractSubscription();
-        $parking = $context->getParking();
-
-        if ($user === null) {
-            throw new AppCommonException("コンテキスト不正 利用者情報");
-        }
-        if ($subscription === null) {
-            throw new AppCommonException("コンテキスト不正 申込情報");
-        }
-        if ($parking === null) {
-            throw new AppCommonException("コンテキスト不正 駐車場情報");
-        }
-
-        $this->email = $user->email;
-        $this->parkName = $parking->park_name;
-        $this->useStartRequestDate = $subscription->use_start_request_date;
-        $this->memo = $subscription->memo ?? "";
-    }
-
-    public function getTemplateName(): string
-    {
-        return 'mails.members.subscription.entry';
-    }
-
-    public function getSubject(): string
-    {
-        return '【スマートパーキングパス】定期申し込み内容';
-    }
-
-    public function getMemberParams(): array
-    {
-        return [
-            'email' => $this->email,
-            'park_name' => $this->parkName,
-            'use_start_request_date' => $this->getUseStartRequestDate(),
-            'memo' => $this->memo
-        ];
-    }
-
-    public function getUseStartRequestDate()
-    {
-        if ($this->useStartRequestDate === null) return "-";
-        return $this->useStartRequestDate->format("Y年m月d日");
-    }
-}
diff --git a/app/Mail/Members/Subscription/Hold.php b/app/Mail/Members/Subscription/Hold.php
deleted file mode 100644
index 747e1c6..0000000
--- a/app/Mail/Members/Subscription/Hold.php
+++ /dev/null
@@ -1,47 +0,0 @@
-<?php
-
-namespace App\Mail\Members\Subscription;
-
-use App\Mail\Members\Member;
-use App\Models\SeasonTicketContractSubscriptionMessage;
-
-class Hold extends Member
-{
-    private string $parkName;
-    private string|null $message;
-
-    /**
-     * Create a new message instance.
-     *
-     * @return void
-     */
-    public function __construct(SeasonTicketContractSubscriptionMessage $message)
-    {
-        $context = $this->context();
-        $parking = $context->getParking();
-        if ($parking === null) {
-            throw new AppCommonException("コンテキスト不正 駐車場情報");
-        }
-
-        $this->parkName = $parking->park_name;
-        $this->message = $message->message;
-    }
-
-    public function getTemplateName(): string
-    {
-        return 'mails.members.subscription.hold';
-    }
-
-    public function getSubject(): string
-    {
-        return '【スマートパーキングパス】申込確認のお知らせ';
-    }
-
-    public function getMemberParams(): array
-    {
-        return [
-            'parkName' => $this->parkName,
-            'memo' => $this->message,
-        ];
-    }
-}
diff --git a/app/Mail/Members/Subscription/Reject.php b/app/Mail/Members/Subscription/Reject.php
deleted file mode 100644
index 53e7e1d..0000000
--- a/app/Mail/Members/Subscription/Reject.php
+++ /dev/null
@@ -1,47 +0,0 @@
-<?php
-
-namespace App\Mail\Members\Subscription;
-
-use App\Mail\Members\Member;
-use App\Models\SeasonTicketContractSubscriptionMessage;
-
-class Reject extends Member
-{
-    private string $parkName;
-    private string $message;
-
-    /**
-     * Create a new message instance.
-     *
-     * @return void
-     */
-    public function __construct(SeasonTicketContractSubscriptionMessage $message)
-    {
-        $context = $this->context();
-        $parking = $context->getParking();
-        if ($parking === null) {
-            throw new AppCommonException("コンテキスト不正 駐車場情報");
-        }
-
-        $this->parkName = $parking->park_name;
-        $this->message = $message->message ?? "";
-    }
-
-    public function getTemplateName(): string
-    {
-        return 'mails.members.subscription.reject';
-    }
-
-    public function getSubject(): string
-    {
-        return '【スマートパーキングパス】申込却下のお知らせ';
-    }
-
-    public function getMemberParams(): array
-    {
-        return [
-            'parkName' => $this->parkName,
-            'memo' => $this->message,
-        ];
-    }
-}
diff --git a/app/Mail/Members/Subscription/Returned.php b/app/Mail/Members/Subscription/Returned.php
deleted file mode 100644
index b0af117..0000000
--- a/app/Mail/Members/Subscription/Returned.php
+++ /dev/null
@@ -1,48 +0,0 @@
-<?php
-
-namespace App\Mail\Members\Subscription;
-
-use App\Mail\Members\Member;
-use App\Models\SeasonTicketContractSubscriptionMessage;
-
-class Returned extends Member
-{
-
-    private string $parkName;
-    private string $message;
-
-    /**
-     * Create a new message instance.
-     *
-     * @return void
-     */
-    public function __construct(SeasonTicketContractSubscriptionMessage $message)
-    {
-        $context = $this->context();
-        $parking = $context->getParking();
-        if ($parking === null) {
-            throw new AppCommonException("コンテキスト不正 駐車場情報");
-        }
-
-        $this->parkName = $parking->park_name;
-        $this->message = $message->message ?? "";
-    }
-
-    public function getTemplateName(): string
-    {
-        return 'mails.members.subscription.returned';
-    }
-
-    public function getSubject(): string
-    {
-        return '【スマートパーキングパス】申込差し戻しのお知らせ';
-    }
-
-    public function getMemberParams(): array
-    {
-        return [
-            'parkName' => $this->parkName,
-            'memo' => $this->message,
-        ];
-    }
-}
diff --git a/app/Mail/Members/UserRegisterComplete.php b/app/Mail/Members/UserRegisterComplete.php
deleted file mode 100644
index fe53a28..0000000
--- a/app/Mail/Members/UserRegisterComplete.php
+++ /dev/null
@@ -1,76 +0,0 @@
-<?php
-
-namespace App\Mail\Members;
-
-use App\Models\ResetPassword;
-use App\Models\User;
-use Illuminate\Support\Carbon;
-
-class UserRegisterComplete extends Member
-{
-
-
-    private string $email;
-
-    private bool $includePasswordReset = false;
-    private Carbon|null $expiresAt = null;
-    private string $token = "";
-
-
-    /**
-     * Create a new message instance.
-     *
-     * @return void
-     */
-    public function __construct(User $model, ResetPassword|null $password = null)
-    {
-        $this->email = $model->email;
-
-        if ($password !== null) {
-            $this->includePasswordReset = true;
-            $this->expiresAt = $password->expires_at;
-            $this->token = $password->token;
-        }
-    }
-
-    public function getTemplateName(): string
-    {
-        return 'mails.members.user_register_complete';
-    }
-
-    public function getSubject(): string
-    {
-        return '【スマートパーキングパス】会員登録完了';
-    }
-
-    public function getMemberParams(): array
-    {
-        return [
-            'email' => $this->email,
-            'includePasswordReset' => $this->includePasswordReset,
-            'url' => $this->getUrl(),
-            'expiresAt' => $this->getExpiresAt(),
-        ];
-    }
-
-    private function getUrl()
-    {
-        return implode(
-            "/",
-            [
-                config("app.url"),
-                'password-reset',
-                $this->token
-            ]
-        );
-    }
-
-    private function getExpiresAt()
-    {
-        if ($this->expiresAt === null) {
-            return "";
-        } else {
-            return $this->expiresAt->format('Y/m/d H:i');
-        }
-    }
-}
diff --git a/app/Models/AppModel.php b/app/Models/AppModel.php
index 8ac7198..d40e4b6 100644
--- a/app/Models/AppModel.php
+++ b/app/Models/AppModel.php
@@ -23,6 +23,8 @@ abstract class AppModel extends BaseModel
 
     public function setId(?string $uuid = null)
     {
+        if ($this->id !== null) return;
+
         if ($uuid) {
             $this->id = $uuid;
         } else {
diff --git a/app/Models/ColumnName.php b/app/Models/ColumnName.php
index a086e01..472f118 100644
--- a/app/Models/ColumnName.php
+++ b/app/Models/ColumnName.php
@@ -19,4 +19,5 @@ abstract class ColumnName
     const RECEIPT_ISSUING_ORDER_ID = "receipt_issuing_order_id";
     const SMS_SEND_ORDER_ID = "sms_send_order_id";
     const SMS_PROVIDER_ID = "sms_provider_id";
+    const EMAIL_ID = "email_id";
 }
diff --git a/app/Models/Email.php b/app/Models/Email.php
index 3de9689..8c7d0bb 100644
--- a/app/Models/Email.php
+++ b/app/Models/Email.php
@@ -2,11 +2,23 @@
 
 namespace App\Models;
 
+use Illuminate\Database\Eloquent\Relations\HasMany;
 
 class Email extends AppModel
 {
+    const COL_NAME_SEND_DATETIME = "send_datetime";
+
     public function getModelName(): string
     {
         return "Email";
     }
+
+    public function emailAttachments(): HasMany
+    {
+        return $this->hasMany(EmailAttachment::class);
+    }
+
+    protected $casts = [
+        self::COL_NAME_SEND_DATETIME => 'datetime',
+    ];
 }
diff --git a/app/Models/EmailAttachment.php b/app/Models/EmailAttachment.php
new file mode 100644
index 0000000..2f7d3a8
--- /dev/null
+++ b/app/Models/EmailAttachment.php
@@ -0,0 +1,17 @@
+<?php
+
+namespace App\Models;
+
+
+class EmailAttachment extends AppModel
+{
+    public function getModelName(): string
+    {
+        return "Email添付ファイル";
+    }
+
+    public function getHistory(): ?HistoryModel
+    {
+        return null;
+    }
+}
diff --git a/app/Models/ReceiptIssuingOrder.php b/app/Models/ReceiptIssuingOrder.php
index 6b5c4b8..00af34a 100644
--- a/app/Models/ReceiptIssuingOrder.php
+++ b/app/Models/ReceiptIssuingOrder.php
@@ -32,6 +32,8 @@ class ReceiptIssuingOrder extends AppModel
     const COL_NAME_STATUS_RECEIPT_EMAIL_SEND_ORDER_DATETIME = "status_receipt_email_send_order_datetime";
     const COL_NAME_STATUS_RECEIPT_EMAIL_SEND_DATETIME = "status_receipt_email_send_datetime";
 
+    const COL_NAME_RECEIPT_PDF_EMAIL_ID = "receipt_pdf_email_id";
+
     const COL_NAME_SMS_PHONE_NUMBER = "sms_phone_number";
     const COL_NAME_SMS_SEND_SUCCESS = "sms_send_success";
     const COL_NAME_RECEIPT_NO = "receipt_no";
@@ -61,6 +63,7 @@ class ReceiptIssuingOrder extends AppModel
         self::COL_NAME_STATUS_MAIL_DOWNLOAD_DATETIME => 'datetime',
         self::COL_NAME_STATUS_MAIL_POST_DATE => 'date',
         self::COL_NAME_STATUS_RECEIPT_DOWNLOAD_DATETIME => 'datetime',
+        self::COL_NAME_STATUS_RECEIPT_EMAIL_SEND_ORDER_DATETIME => 'datetime',
         self::COL_NAME_STATUS_RECEIPT_EMAIL_SEND_DATETIME => 'datetime',
         self::COL_NAME_RECEIPT_USE_DATE => 'date',
         self::COL_NAME_MAIL_PREF_CODE => PrefCode::class,
diff --git a/app/Util/MigrationHelper.php b/app/Util/MigrationHelper.php
index 9371373..5b56a57 100644
--- a/app/Util/MigrationHelper.php
+++ b/app/Util/MigrationHelper.php
@@ -78,6 +78,9 @@ class MigrationHelper
         $this->table->timestamp(ColumnName::UPDATED_AT)->nullable()->comment("更新日時");
         $this->table->timestamp(ColumnName::DELETED_AT)->nullable()->comment("論理削除日時");
 
+        $this->table->index([ColumnName::CREATED_AT], sprintf("%s_idx_CREATED_AT", $this->table->getTable()));
+        $this->table->index([ColumnName::UPDATED_AT], sprintf("%s_idx_UPDATED_AT", $this->table->getTable()));
+
         return $this;
     }
 
@@ -159,4 +162,10 @@ class MigrationHelper
         // $this->table->foreign(ColumnName::SMS_PROVIDER_ID)->references(ColumnName::ID)->on(SMSProvider::getTableName());
         return $this;
     }
+
+    public  function emailId(bool $nullable = false)
+    {
+        $this->table->uuid(ColumnName::EMAIL_ID)->comment("EメールID")->nullable($nullable);
+        return $this;
+    }
 }
diff --git a/config/mail.php b/config/mail.php
index 542d98c..b3851fd 100644
--- a/config/mail.php
+++ b/config/mail.php
@@ -43,6 +43,8 @@ return [
             'password' => env('MAIL_PASSWORD'),
             'timeout' => null,
             'local_domain' => env('MAIL_EHLO_DOMAIN'),
+            'auth_mode'  => null,
+            'verify_peer' => false,
         ],
 
         'ses' => [
diff --git a/database/migrations/2023_07_11_134700_create_email_attachments_table.php b/database/migrations/2023_07_11_134700_create_email_attachments_table.php
new file mode 100644
index 0000000..48060e6
--- /dev/null
+++ b/database/migrations/2023_07_11_134700_create_email_attachments_table.php
@@ -0,0 +1,46 @@
+<?php
+
+use App\Models\ColumnName;
+use App\Util\MigrationHelper;
+use Illuminate\Database\Migrations\Migration;
+use Illuminate\Database\Schema\Blueprint;
+use Illuminate\Support\Facades\Schema;
+
+return new class extends Migration
+{
+    /**
+     * Run the migrations.
+     *
+     * @return void
+     */
+    public function up()
+    {
+        MigrationHelper::createTable('email_attachments', $this->schema());
+    }
+
+    /**
+     * Reverse the migrations.
+     *
+     * @return void
+     */
+    public function down()
+    {
+        Schema::dropIfExists('email_attachments');
+    }
+
+    private function schema()
+    {
+
+        return function (Blueprint $table,  MigrationHelper $helper) {
+            $helper->baseColumn()
+                ->emailId();
+
+            $table->string('filepath')->comment("ファイルパス");
+            $table->string('send_filename')->comment("送信ファイル名");
+            $table->string('mime')->comment("MIMEタイプ");
+
+            $helper->index(1, [ColumnName::EMAIL_ID]);
+            $helper->index(2, [ColumnName::CREATED_AT]);
+        };
+    }
+};
diff --git a/database/migrations/2023_07_12_161800_add_column_receipt_issuing_orders_table_email_id.php b/database/migrations/2023_07_12_161800_add_column_receipt_issuing_orders_table_email_id.php
new file mode 100644
index 0000000..0cd5b6d
--- /dev/null
+++ b/database/migrations/2023_07_12_161800_add_column_receipt_issuing_orders_table_email_id.php
@@ -0,0 +1,40 @@
+<?php
+
+use App\Models\ColumnName;
+use App\Util\MigrationHelper;
+use Illuminate\Database\Migrations\Migration;
+use Illuminate\Database\Schema\Blueprint;
+use Illuminate\Support\Facades\Schema;
+
+return new class extends Migration
+{
+    /**
+     * Run the migrations.
+     *
+     * @return void
+     */
+    public function up()
+    {
+        Schema::table('receipt_issuing_orders', function (Blueprint $table) {
+            $table->uuid("receipt_pdf_email_id")->nullable()->comment("領収書PDF送付EmailID");
+        });
+        Schema::table('receipt_issuing_order_histories', function (Blueprint $table) {
+            $table->uuid("receipt_pdf_email_id")->nullable()->comment("領収書PDF送付EmailID");
+        });
+    }
+
+    /**
+     * Reverse the migrations.
+     *
+     * @return void
+     */
+    public function down()
+    {
+        Schema::table('receipt_issuing_orders', function (Blueprint $table) {
+            $table->dropColumn("receipt_pdf_email_id");
+        });
+        Schema::table('receipt_issuing_order_histories', function (Blueprint $table) {
+            $table->dropColumn("receipt_pdf_email_id");
+        });
+    }
+};
diff --git a/deploy.sh b/deploy.sh
index bc91294..86b9345 100644
--- a/deploy.sh
+++ b/deploy.sh
@@ -20,6 +20,7 @@ COMMANDS+=("${SAIL} php artisan config:cache")
 COMMANDS+=("${SAIL} php artisan route:cache")
 COMMANDS+=("${SAIL} php artisan view:cache")
 COMMANDS+=("${SAIL} php artisan event:cache")
+COMMANDS+=("${SAIL} php artisan queue:restart")
 
 for COMMAND in "${COMMANDS[@]}"; do
     echo ${COMMAND} 
diff --git a/resources/views/mails/components/ask_confirmation.blade.php b/resources/views/mails/components/ask_confirmation.blade.php
deleted file mode 100644
index eb2e4ab..0000000
--- a/resources/views/mails/components/ask_confirmation.blade.php
+++ /dev/null
@@ -1,14 +0,0 @@
-下記内容にてお問合せを受付ました。
-返信のメールがあるまでしばらくお待ちください。
-
-件名: {{ $askSubject }}
-@if($parkName)
-駐車場名 : {{ $parkName }}
-@endif
-
-■問い合わせ内容
-{{ $askContents }}
-
-■問い合わせ者情報
-氏名: {{ $userName }}
-email: {{ $userEmail }}
\ No newline at end of file
diff --git a/resources/views/mails/components/season_ticket_contract/how_to_register_ic_card.blade.php b/resources/views/mails/components/season_ticket_contract/how_to_register_ic_card.blade.php
deleted file mode 100644
index 08a14a3..0000000
--- a/resources/views/mails/components/season_ticket_contract/how_to_register_ic_card.blade.php
+++ /dev/null
@@ -1,7 +0,0 @@
-　①駐車場に設置された定期更新機で利用したい交通系ICカード（ICOCA,SUICAなど）をタッチします。
-　②画面が切り替わりますので、上記定期券番号と確認コードを入力して確定ボタンを押してください。
-　　または、承認画面で認証用QRコードをかざしても定期券登録が完了します。
-@isset($my_qr_code_url)
-　認証用QRコードは以下（初回アクセスの場合はパスワードを設定してログインしてください）
-　{{ $my_qr_code_url }}
-@endisset
\ No newline at end of file
diff --git a/resources/views/mails/components/send_only.blade.php b/resources/views/mails/components/send_only.blade.php
deleted file mode 100644
index 46c35fc..0000000
--- a/resources/views/mails/components/send_only.blade.php
+++ /dev/null
@@ -1 +0,0 @@
-※このメールをお送りしているアドレスは、送信専用となっており、返信いただいてもご回答いたしかねます。
\ No newline at end of file
diff --git a/resources/views/mails/guests/receipt_a4.blade.php b/resources/views/mails/guests/receipt_a4.blade.php
new file mode 100644
index 0000000..ff09c7c
--- /dev/null
+++ b/resources/views/mails/guests/receipt_a4.blade.php
@@ -0,0 +1,15 @@
+@extends('mails.layouts.guest')
+
+@section('contents')
+発行依頼された領収証を添付します。
+ご確認よろしくお願いいたします。
+
+■店舗名
+{{ $shopName }}
+
+■利用日
+{{ $useDate }}
+
+■金額
+{{ $amount }}円
+@endsection
\ No newline at end of file
diff --git a/resources/views/mails/layouts/guest.blade.php b/resources/views/mails/layouts/guest.blade.php
new file mode 100644
index 0000000..c610e35
--- /dev/null
+++ b/resources/views/mails/layouts/guest.blade.php
@@ -0,0 +1,11 @@
+ご利用ありがとうございます。
+EasyReceiptです。
+
+@yield('contents')
+
+
+※このメールをお送りしているアドレスは、送信専用となっており、返信いただいてもご回答いたしかねます。
+※このメールにお心当たりのない方は、お手数ですが削除いただきますようお願いいたします。
+
+---------------------------------------------------------------------------------------
+EasyReceipt
\ No newline at end of file
diff --git a/routes/api.php b/routes/api.php
index 0a92e0f..247e926 100644
--- a/routes/api.php
+++ b/routes/api.php
@@ -20,6 +20,7 @@ RouteHelper::post('/change-contract', App\Http\Controllers\Web\Auth\ChangeContra
 
 RouteHelper::get('/app-token-check', App\Http\Controllers\Web\ReceiptIssuingOrder\TokenCheckController::class);
 RouteHelper::post('/receipt-issuing-order/confirm', App\Http\Controllers\Web\ReceiptIssuingOrder\ConfirmController::class);
+RouteHelper::post('/receipt-issuing-order/email-order', App\Http\Controllers\Web\ReceiptIssuingOrder\EmailOrderController::class);
 RouteHelper::post('/receipt-issuing-order/mail-order', App\Http\Controllers\Web\ReceiptIssuingOrder\MailOrderController::class);
 RouteHelper::post('/receipt-issuing-order/mail-complete', App\Http\Controllers\Web\ReceiptIssuingOrder\MailPostCompleteController::class);
 RouteHelper::post('/receipt-issuing-order/change-handler', App\Http\Controllers\Web\ReceiptIssuingOrder\ChangeHandlerController::class);