diff --git a/app/Console/Commands/CreateTestData.php b/app/Console/Commands/CreateTestData.php
index 40d74f98e2b9..8124381d36d4 100644
--- a/app/Console/Commands/CreateTestData.php
+++ b/app/Console/Commands/CreateTestData.php
@@ -11,6 +11,7 @@ use App\Factory\InvoiceItemFactory;
 use App\Factory\PaymentFactory;
 use App\Helpers\Invoice\InvoiceSum;
 use App\Jobs\Company\UpdateCompanyLedgerWithInvoice;
+use App\Jobs\Invoice\CreateInvoiceInvitations;
 use App\Jobs\Invoice\UpdateInvoicePayment;
 use App\Listeners\Invoice\CreateInvoiceInvitation;
 use App\Models\CompanyToken;
@@ -316,8 +317,8 @@ class CreateTestData extends Command
 
             $this->invoice_repo->markSent($invoice);
 
-            event(new InvoiceWasMarkedSent($invoice));
-
+                CreateInvoiceInvitations::dispatch($invoice);
+                
             if(rand(0, 1)) {
 
                 $payment = PaymentFactory::create($client->company->id, $client->user->id);
diff --git a/app/Console/Commands/SendTestEmails.php b/app/Console/Commands/SendTestEmails.php
index d6ccaf04b329..f46f14e62d85 100644
--- a/app/Console/Commands/SendTestEmails.php
+++ b/app/Console/Commands/SendTestEmails.php
@@ -2,7 +2,10 @@
 
 namespace App\Console\Commands;
 
+use App\Factory\ClientFactory;
 use App\Mail\TemplateEmail;
+use App\Models\Client;
+use App\Models\ClientContact;
 use App\Models\Invoice;
 use App\Models\User;
 use Illuminate\Console\Command;
@@ -43,7 +46,9 @@ class SendTestEmails extends Command
     public function handle()
     {
         $this->sendTemplateEmails('plain');
+        sleep(5);
         $this->sendTemplateEmails('light');
+        sleep(5);
         $this->sendTemplateEmails('dark');
     }
 
@@ -57,21 +62,48 @@ class SendTestEmails extends Command
         ];
 
         $user = User::whereEmail('user@example.com')->first();
+        $client = Client::all()->first();
 
         if(!$user){
             $user = factory(\App\Models\User::class)->create([
                 'confirmation_code' => '123',
+                'email' => 'admin@business.com',
+                'first_name' => 'John',
+                'last_name' => 'Doe',
+            ]);
+        }
+
+        if(!$client) {
+             
+             $client = ClientFactory::create($user->company()->id, $user->id);
+             $client->save();
+
+            factory(\App\Models\ClientContact::class,1)->create([
+                'user_id' => $user->id,
+                'client_id' => $client->id,
+                'company_id' => $company->id,
+                'is_primary' => 1,
+                'send_invoice' => true,
+                'email' => 'exy@example.com',
+            ]);
+
+            factory(\App\Models\ClientContact::class,1)->create([
+                'user_id' => $user->id,
+                'client_id' => $client->id,
+                'company_id' => $company->id,
+                'send_invoice' => true,
+                'email' => 'exy2@example.com',
             ]);
         }
 
          $cc_emails = [config('ninja.testvars.test_email')];
          $bcc_emails = [config('ninja.testvars.test_email')];
 
-        Mail::to(config('ninja.testvars.test_email'))
+        Mail::to(config('ninja.testvars.test_email'),'Mr Test')
             ->cc($cc_emails)
             ->bcc($bcc_emails)
             //->replyTo(also_available_if_needed)
-            ->send(new TemplateEmail($message, $template, $user));
+            ->send(new TemplateEmail($message, $template, $user, $client));
     }
 
 }
diff --git a/app/DataMapper/CompanySettings.php b/app/DataMapper/CompanySettings.php
index b2b4937286ec..7972918cf86c 100644
--- a/app/DataMapper/CompanySettings.php
+++ b/app/DataMapper/CompanySettings.php
@@ -69,6 +69,7 @@ class CompanySettings extends BaseSettings
 	public $translations;
 
 	public $counter_number_applied = 'when_saved'; // when_saved , when_sent , when_paid 
+	public $quote_number_applied = 'when_saved'; // when_saved , when_sent
 	/* Counters */
 	public $invoice_number_pattern = '';
 	public $invoice_number_counter = 1;
@@ -222,6 +223,7 @@ class CompanySettings extends BaseSettings
 		'gmail_sending_user_id' => 'string',
 		'currency_id' => 'string',
 		'counter_number_applied' => 'string',
+		'quote_number_applied' => 'string',
 		'email_subject_custom1' => 'string',
 		'email_subject_custom2' => 'string',
 		'email_subject_custom3' => 'string',
diff --git a/app/Events/Invoice/InvoiceWasEmailed.php b/app/Events/Invoice/InvoiceWasEmailed.php
index 459e57e4cfe0..86c1ab7610c4 100644
--- a/app/Events/Invoice/InvoiceWasEmailed.php
+++ b/app/Events/Invoice/InvoiceWasEmailed.php
@@ -26,19 +26,13 @@ class InvoiceWasEmailed
      */
     public $invoice;
 
-    /**
-     * @var string
-     */
-    public $notes;
-
     /**
      * Create a new event instance.
      *
      * @param Invoice $invoice
      */
-    public function __construct(Invoice $invoice, $notes)
+    public function __construct(Invoice $invoice)
     {
         $this->invoice = $invoice;
-        $this->notes = $notes;
     }
 }
diff --git a/app/Events/Invoice/InvoiceWasEmailedAndFailed.php b/app/Events/Invoice/InvoiceWasEmailedAndFailed.php
new file mode 100644
index 000000000000..f8a814ff1bcf
--- /dev/null
+++ b/app/Events/Invoice/InvoiceWasEmailedAndFailed.php
@@ -0,0 +1,45 @@
+<?php
+/**
+ * Invoice Ninja (https://invoiceninja.com)
+ *
+ * @link https://github.com/invoiceninja/invoiceninja source repository
+ *
+ * @copyright Copyright (c) 2019. Invoice Ninja LLC (https://invoiceninja.com)
+ *
+ * @license https://opensource.org/licenses/AAL
+ */
+
+namespace App\Events\Invoice;
+
+use App\Models\Invoice;
+use Illuminate\Queue\SerializesModels;
+
+/**
+ * Class InvoiceWasEmailedAndFailed.
+ */
+class InvoiceWasEmailedAndFailed 
+{
+    use SerializesModels;
+
+    /**
+     * @var Invoice
+     */
+    public $invoice;
+
+    /**
+     * @var array
+     */
+    public $errors;
+
+    /**
+     * Create a new event instance.
+     *
+     * @param Invoice $invoice
+     */
+    public function __construct(Invoice $invoice, array $errors)
+    {
+        $this->invoice = $invoice;
+        
+        $this->errors = $errors;
+    }
+}
diff --git a/app/Http/Controllers/InvoiceController.php b/app/Http/Controllers/InvoiceController.php
index 8fbd0c9fd5c4..35eae3b4866a 100644
--- a/app/Http/Controllers/InvoiceController.php
+++ b/app/Http/Controllers/InvoiceController.php
@@ -25,6 +25,7 @@ use App\Http\Requests\Invoice\ShowInvoiceRequest;
 use App\Http\Requests\Invoice\StoreInvoiceRequest;
 use App\Http\Requests\Invoice\UpdateInvoiceRequest;
 use App\Jobs\Entity\ActionEntity;
+use App\Jobs\Invoice\EmailInvoice;
 use App\Jobs\Invoice\MarkInvoicePaid;
 use App\Jobs\Invoice\StoreInvoice;
 use App\Models\Invoice;
@@ -660,7 +661,7 @@ class InvoiceController extends BaseController
                 return $this->listResponse($invoice);
                 break;
             case 'email':
-
+                EmailInvoice::dispatch($invoice);
                 if(!$bulk)
                 return response()->json(['message'=>'email sent'],200);
                 break;
diff --git a/app/Http/Controllers/OpenAPI/CompanySettingsSchema.php b/app/Http/Controllers/OpenAPI/CompanySettingsSchema.php
index 199d456998e8..dedfa1b499c9 100644
--- a/app/Http/Controllers/OpenAPI/CompanySettingsSchema.php
+++ b/app/Http/Controllers/OpenAPI/CompanySettingsSchema.php
@@ -21,10 +21,11 @@
  *       @OA\Property(property="email_style", type="string", example="light", description="options include plain,light,dark,custom"),
  *       @OA\Property(property="reply_to_email", type="string", example="email@gmail.com", description="The reply to email address"),
  *       @OA\Property(property="bcc_email", type="string", example="email@gmail.com, contact@gmail.com", description="A comma separate list of BCC emails"),
- *       
  *       @OA\Property(property="pdf_email_attachment", type="boolean", example=true, description="Toggles whether to attach PDF as attachment"),
  *       @OA\Property(property="ubl_email_attachment", type="boolean", example=true, description="Toggles whether to attach UBL as attachment"),
  *       @OA\Property(property="email_style_custom", type="string", example="<HTML></HTML>", description="The custom template"),
+ *       @OA\Property(property="counter_number_applied", type="string", example="when_sent", description="enum when the invoice number counter is set, ie when_saved, when_sent, when_paid"),
+ *       @OA\Property(property="quote_number_applied", type="string", example="when_sent", description="enum when the quote number counter is set, ie when_saved, when_sent"),
  *       @OA\Property(property="custom_message_dashboard", type="string", example="Please pay invoices immediately", description="____________"),
  *       @OA\Property(property="custom_message_unpaid_invoice", type="string", example="Please pay invoices immediately", description="____________"),
  *       @OA\Property(property="custom_message_paid_invoice", type="string", example="Thanks for paying this invoice!", description="____________"),
@@ -44,7 +45,6 @@
  *       @OA\Property(property="vendor_number_counter", type="integer", example="1", description="____________"),
  *       @OA\Property(property="ticket_number_pattern", type="string", example="{$year}-{$counter}", description="Allows customisation of the ticket number pattern"),
  *       @OA\Property(property="ticket_number_counter", type="integer", example="1", description="____________"),
- *
  *       @OA\Property(property="payment_number_pattern", type="string", example="{$year}-{$counter}", description="Allows customisation of the payment number pattern"),
  *       @OA\Property(property="payment_number_counter", type="integer", example="1", description="____________"),
  *       @OA\Property(property="invoice_number_pattern", type="string", example="{$year}-{$counter}", description="Allows customisation of the invoice number pattern"),
diff --git a/app/Http/Controllers/OpenAPI/InvoiceSchema.php b/app/Http/Controllers/OpenAPI/InvoiceSchema.php
index 0ec8d8f0f185..d5acc258330e 100644
--- a/app/Http/Controllers/OpenAPI/InvoiceSchema.php
+++ b/app/Http/Controllers/OpenAPI/InvoiceSchema.php
@@ -5,10 +5,10 @@
  *   type="object",
  *       @OA\Property(property="id", type="string", example="Opnel5aKBz", description="_________"),
  *       @OA\Property(property="user_id", type="string", example="", description="__________"),
+ *       @OA\Property(property="assigned_user_id", type="string", example="", description="__________"),
  *       @OA\Property(property="company_id", type="string", example="", description="________"),
  *       @OA\Property(property="client_id", type="string", example="", description="________"),
  *       @OA\Property(property="status_id", type="string", example="", description="________"),
- *       @OA\Property(property="invoice_type_id", type="string", example="", description="________"),
  *       @OA\Property(property="number", type="string", example="INV_101", description="The invoice number - is a unique alpha numeric number per invoice per company"),
  *       @OA\Property(property="po_number", type="string", example="", description="________"),
  *       @OA\Property(property="terms", type="string", example="", description="________"),
@@ -35,6 +35,7 @@
  *       @OA\Property(property="is_deleted", type="boolean", example=true, description="_________"),
  *       @OA\Property(property="uses_inclusive_taxes", type="boolean", example=true, description="Defines the type of taxes used as either inclusive or exclusive"),
  *       @OA\Property(property="date", type="string", format="date", example="1994-07-30", description="The Invoice Date"),
+ *       @OA\Property(property="last_sent_date", type="string", format="date", example="1994-07-30", description="The last date the invoice was sent out"),
  *       @OA\Property(property="next_send_date", type="string", format="date", example="1994-07-30", description="The Next date for a reminder to be sent"),
  *       @OA\Property(property="partial_due_date", type="string", format="date", example="1994-07-30", description="_________"),
  *       @OA\Property(property="due_date", type="string", format="date", example="1994-07-30", description="_________"),
diff --git a/app/Http/Controllers/OpenAPI/QuoteSchema.php b/app/Http/Controllers/OpenAPI/QuoteSchema.php
index 066d7370f9f8..ef78305a8bab 100644
--- a/app/Http/Controllers/OpenAPI/QuoteSchema.php
+++ b/app/Http/Controllers/OpenAPI/QuoteSchema.php
@@ -3,8 +3,50 @@
  * @OA\Schema(
  *   schema="Quote",
  *   type="object",
- *       @OA\Property(property="id", type="string", example="Opnel5aKBz", description="______"),
+ *       @OA\Property(property="id", type="string", example="Opnel5aKBz", description="_________"),
+ *       @OA\Property(property="user_id", type="string", example="", description="__________"),
+ *       @OA\Property(property="assigned_user_id", type="string", example="", description="__________"),
+ *       @OA\Property(property="company_id", type="string", example="", description="________"),
+ *       @OA\Property(property="client_id", type="string", example="", description="________"),
+ *       @OA\Property(property="status_id", type="string", example="", description="________"),
+ *       @OA\Property(property="number", type="string", example="QUOTE_101", description="The quote number - is a unique alpha numeric number per quote per company"),
+ *       @OA\Property(property="po_number", type="string", example="", description="________"),
+ *       @OA\Property(property="terms", type="string", example="", description="________"),
+ *       @OA\Property(property="public_notes", type="string", example="", description="________"),
+ *       @OA\Property(property="private_notes", type="string", example="", description="________"),
+ *       @OA\Property(property="footer", type="string", example="", description="________"),
+ *       @OA\Property(property="custom_value1", type="string", example="", description="________"),
+ *       @OA\Property(property="custom_value2", type="string", example="", description="________"),
+ *       @OA\Property(property="custom_value3", type="string", example="", description="________"),
+ *       @OA\Property(property="custom_value4", type="string", example="", description="________"),
+ *       @OA\Property(property="tax_name1", type="string", example="", description="________"),
+ *       @OA\Property(property="tax_name2", type="string", example="", description="________"),
+ *       @OA\Property(property="tax_rate1", type="number", format="float", example="10.00", description="_________"),
+ *       @OA\Property(property="tax_rate2", type="number", format="float", example="10.00", description="_________"),
+ *       @OA\Property(property="tax_name3", type="string", example="", description="________"),
+ *       @OA\Property(property="tax_rate3", type="number", format="float", example="10.00", description="_________"),
  *       @OA\Property(property="total_taxes", type="number", format="float", example="10.00", description="The total taxes for the quote"),
+ *       @OA\Property(property="line_items", type="object", example="", description="_________"),
+ *       @OA\Property(property="amount", type="number", format="float", example="10.00", description="_________"),
+ *       @OA\Property(property="balance", type="number", format="float", example="10.00", description="_________"),
+ *       @OA\Property(property="discount", type="number", format="float", example="10.00", description="_________"),
+ *       @OA\Property(property="partial", type="number", format="float", example="10.00", description="_________"),
+ *       @OA\Property(property="is_amount_discount", type="boolean", example=true, description="_________"),
+ *       @OA\Property(property="is_deleted", type="boolean", example=true, description="_________"),
+ *       @OA\Property(property="uses_inclusive_taxes", type="boolean", example=true, description="Defines the type of taxes used as either inclusive or exclusive"),
+ *       @OA\Property(property="date", type="string", format="date", example="1994-07-30", description="The Quote Date"),
+ *       @OA\Property(property="last_sent_date", type="string", format="date", example="1994-07-30", description="The last date the quote was sent out"),
  *       @OA\Property(property="next_send_date", type="string", format="date", example="1994-07-30", description="The Next date for a reminder to be sent"),
+ *       @OA\Property(property="partial_due_date", type="string", format="date", example="1994-07-30", description="_________"),
+ *       @OA\Property(property="due_date", type="string", format="date", example="1994-07-30", description="_________"),
+ *       @OA\Property(property="settings",ref="#/components/schemas/CompanySettings"),
+ *       @OA\Property(property="last_viewed", type="number", format="integer", example="1434342123", description="Timestamp"),
+ *       @OA\Property(property="updated_at", type="number", format="integer", example="1434342123", description="Timestamp"),
+ *       @OA\Property(property="archived_at", type="number", format="integer", example="1434342123", description="Timestamp"),
+ *       @OA\Property(property="custom_surcharge1", type="number", format="float", example="10.00", description="First Custom Surcharge"),
+ *       @OA\Property(property="custom_surcharge2", type="number", format="float", example="10.00", description="Second Custom Surcharge"),
+ *       @OA\Property(property="custom_surcharge3", type="number", format="float", example="10.00", description="Third Custom Surcharge"),
+ *       @OA\Property(property="custom_surcharge4", type="number", format="float", example="10.00", description="Fourth Custom Surcharge"),
+ *       @OA\Property(property="custom_surcharge_taxes", type="boolean", example=true, description="Toggles charging taxes on custom surcharge amounts"),
  * )
  */
\ No newline at end of file
diff --git a/app/Jobs/Invoice/EmailInvoice.php b/app/Jobs/Invoice/EmailInvoice.php
new file mode 100644
index 000000000000..b7d519313146
--- /dev/null
+++ b/app/Jobs/Invoice/EmailInvoice.php
@@ -0,0 +1,111 @@
+<?php
+/**
+ * Invoice Ninja (https://invoiceninja.com)
+ *
+ * @link https://github.com/invoiceninja/invoiceninja source repository
+ *
+ * @copyright Copyright (c) 2019. Invoice Ninja LLC (https://invoiceninja.com)
+ *
+ * @license https://opensource.org/licenses/AAL
+ */
+
+namespace App\Jobs\Invoice;
+
+use App\Events\Invoice\InvoiceWasEmailed;
+use App\Events\Invoice\InvoiceWasEmailedAndFailed;
+use App\Libraries\MultiDB;
+use App\Mail\TemplateEmail;
+use App\Models\Invoice;
+use App\Models\SystemLog;
+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\Facades\Mail;
+
+class EmailInvoice implements ShouldQueue
+{
+    use Dispatchable, InteractsWithQueue, Queueable, SerializesModels;
+
+    public $invoice;
+
+    /**
+     * Create a new job instance.
+     *
+     * @return void
+     */
+    public function __construct(Invoice $invoice)
+    {
+
+        $this->invoice = $invoice;
+
+    }
+
+    /**
+     * Execute the job.
+     *
+     * 
+     * @return void
+     */
+    public function handle()
+    {
+        /*Jobs are not multi-db aware, need to set! */
+        MultiDB::setDB($this->invoice->company->db);
+
+        $message_array = $this->invoice->getEmailData();
+        $message_array['title'] = &$message_array['subject'];
+        $message_array['footer'] = 'The Footer';
+        //
+
+        $variables = array_merge($this->invoice->makeLabels(), $this->invoice->makeValues());
+
+        $template_style = $this->invoice->client->getSetting('email_style');
+        
+        $this->invoice->invitations->each(function ($invitation) use($message_array, $template_style, $variables){
+
+            if($invitation->contact->send_invoice && $invitation->contact->email)
+            {
+                //there may be template variables left over for the specific contact? need to reparse here //todo this wont work, as if the variables existed, they'll be overwritten already!
+                $message_array['body'] = str_replace(array_keys($variables), array_values($variables), $message_array['body']);
+                $message_array['subject'] = str_replace(array_keys($variables), array_values($variables), $message_array['subject']);
+
+                //change the runtime config of the mail provider here:
+                
+                //send message
+                Mail::to($invitation->contact->email)
+                ->send(new TemplateEmail($message_array, $template_style, $invitation->contact->user, $invitation->contact->client));
+
+                if( count(Mail::failures()) > 0 ) {
+
+                    event(new InvoiceWasEmailedAndFailed($this->invoice, Mail::failures()));
+                    
+                    return $this->logMailError($errors);
+
+                }
+
+                //fire any events
+                event(new InvoiceWasEmailed($this->invoice));
+
+                sleep(5);
+                
+            }
+
+        });
+
+    }
+
+    private function logMailError($errors)
+    {
+
+        SystemLogger::dispatch(
+            $errors,
+            SystemLog::CATEGORY_MAIL,
+            SystemLog::EVENT_MAIL_SEND,
+            SystemLog::TYPE_FAILURE,
+            $this->invoice->client
+        );
+
+    }
+
+}
\ No newline at end of file
diff --git a/app/Jobs/Invoice/UpdateInvoicePayment.php b/app/Jobs/Invoice/UpdateInvoicePayment.php
index 6f5fa686d4a3..de64bc658d7e 100644
--- a/app/Jobs/Invoice/UpdateInvoicePayment.php
+++ b/app/Jobs/Invoice/UpdateInvoicePayment.php
@@ -137,7 +137,8 @@ class UpdateInvoicePayment implements ShouldQueue
                         'invoices' => $invoices,
                         'invoices_total' => $invoices_total,
                         'payment_amount' => $this->payment->amount,
-                        'partial_check_amount' => $total,                    ],
+                        'partial_check_amount' => $total,
+                    ],                    
                     SystemLog::CATEGORY_GATEWAY_RESPONSE,
                     SystemLog::EVENT_PAYMENT_RECONCILIATION_FAILURE,
                     SystemLog::TYPE_LEDGER,
diff --git a/app/Jobs/Quote/ApplyQuoteNumber.php b/app/Jobs/Quote/ApplyQuoteNumber.php
new file mode 100644
index 000000000000..cdd8e9ac3996
--- /dev/null
+++ b/app/Jobs/Quote/ApplyQuoteNumber.php
@@ -0,0 +1,81 @@
+<?php
+/**
+ * Quote Ninja (https://invoiceninja.com)
+ *
+ * @link https://github.com/invoiceninja/invoiceninja source repository
+ *
+ * @copyright Copyright (c) 2019. Quote Ninja LLC (https://invoiceninja.com)
+ *
+ * @license https://opensource.org/licenses/AAL
+ */
+
+namespace App\Jobs\Quote;
+
+use App\Models\Quote;
+use App\Models\Payment;
+use App\Models\PaymentTerm;
+use App\Repositories\QuoteRepository;
+use App\Utils\Traits\GeneratesCounter;
+use App\Utils\Traits\NumberFormatter;
+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;
+
+class ApplyQuoteNumber implements ShouldQueue
+{
+    use Dispatchable, InteractsWithQueue, Queueable, SerializesModels, NumberFormatter, GeneratesCounter;
+
+    private $quote;
+
+    private $settings;
+
+    /**
+     * Create a new job instance.
+     *
+     * @return void
+     */
+    public function __construct(Quote $quote, $settings)
+    {
+
+        $this->quote = $quote;
+
+        $this->settings = $settings;
+    }
+
+    /**
+     * Execute the job.
+     *
+     * 
+     * @return void
+     */
+    public function handle()
+    {
+        //return early
+        if($this->quote->number != '')
+            return $this->quote;
+
+        switch ($this->settings->quote_number_applied) {
+            case 'when_saved':
+                $this->quote->number = $this->getNextQuoteNumber($this->quote->client);
+                break;
+            case 'when_sent':
+                if($this->quote->status_id == Quote::STATUS_SENT)
+                    $this->quote->number = $this->getNextQuoteNumber($this->quote->client);
+                break;
+            
+            default:
+                # code...
+                break;
+        }
+   
+        $this->quote->save();
+            
+        return $this->quote;
+
+    }
+
+
+}
diff --git a/app/Listeners/Invoice/InvoiceEmailActivity.php b/app/Listeners/Invoice/InvoiceEmailActivity.php
new file mode 100644
index 000000000000..b382adcfd9f8
--- /dev/null
+++ b/app/Listeners/Invoice/InvoiceEmailActivity.php
@@ -0,0 +1,54 @@
+<?php
+/**
+ * Invoice Ninja (https://invoiceninja.com)
+ *
+ * @link https://github.com/invoiceninja/invoiceninja source repository
+ *
+ * @copyright Copyright (c) 2019. Invoice Ninja LLC (https://invoiceninja.com)
+ *
+ * @license https://opensource.org/licenses/AAL
+ */
+
+namespace App\Listeners\Invoice;
+
+use App\Models\Activity;
+use App\Models\ClientContact;
+use App\Models\InvoiceInvitation;
+use App\Repositories\ActivityRepository;
+use App\Utils\Traits\MakesHash;
+use Illuminate\Contracts\Queue\ShouldQueue;
+use Illuminate\Queue\InteractsWithQueue;
+use Illuminate\Support\Facades\Log;
+
+class InvoiceEmailActivity implements ShouldQueue
+{
+    protected $activity_repo;
+    /**
+     * Create the event listener.
+     *
+     * @return void
+     */
+    public function __construct(ActivityRepository $activity_repo)
+    {
+        $this->activity_repo = $activity_repo;
+    }
+
+    /**
+     * Handle the event.
+     *
+     * @param  object  $event
+     * @return void
+     */
+    public function handle($event)
+    {
+
+        $fields = new \stdClass;
+
+        $fields->invoice_id = $event->invoice->id;
+        $fields->user_id = $event->invoice->user_id;
+        $fields->company_id = $event->invoice->company_id;
+        $fields->activity_type_id = Activity::EMAIL_INVOICE;
+
+        $this->activity_repo->save($fields, $event->invoice);
+    }
+}
diff --git a/app/Listeners/Invoice/InvoiceEmailFailedActivity.php b/app/Listeners/Invoice/InvoiceEmailFailedActivity.php
new file mode 100644
index 000000000000..0f653e5c43fe
--- /dev/null
+++ b/app/Listeners/Invoice/InvoiceEmailFailedActivity.php
@@ -0,0 +1,54 @@
+<?php
+/**
+ * Invoice Ninja (https://invoiceninja.com)
+ *
+ * @link https://github.com/invoiceninja/invoiceninja source repository
+ *
+ * @copyright Copyright (c) 2019. Invoice Ninja LLC (https://invoiceninja.com)
+ *
+ * @license https://opensource.org/licenses/AAL
+ */
+
+namespace App\Listeners\Invoice;
+
+use App\Models\Activity;
+use App\Models\ClientContact;
+use App\Models\InvoiceInvitation;
+use App\Repositories\ActivityRepository;
+use App\Utils\Traits\MakesHash;
+use Illuminate\Contracts\Queue\ShouldQueue;
+use Illuminate\Queue\InteractsWithQueue;
+use Illuminate\Support\Facades\Log;
+
+class InvoiceEmailFailedActivity implements ShouldQueue
+{
+    protected $activity_repo;
+    /**
+     * Create the event listener.
+     *
+     * @return void
+     */
+    public function __construct(ActivityRepository $activity_repo)
+    {
+        $this->activity_repo = $activity_repo;
+    }
+
+    /**
+     * Handle the event.
+     *
+     * @param  object  $event
+     * @return void
+     */
+    public function handle($event)
+    {
+
+        $fields = new \stdClass;
+
+        $fields->invoice_id = $event->invoice->id;
+        $fields->user_id = $event->invoice->user_id;
+        $fields->company_id = $event->invoice->company_id;
+        $fields->activity_type_id = Activity::EMAIL_INVOICE_FAILED;
+
+        $this->activity_repo->save($fields, $event->invoice);
+    }
+}
diff --git a/app/Mail/TemplateEmail.php b/app/Mail/TemplateEmail.php
index 99fda55470f5..c8a4ced4a1c8 100644
--- a/app/Mail/TemplateEmail.php
+++ b/app/Mail/TemplateEmail.php
@@ -14,7 +14,7 @@ class TemplateEmail extends Mailable
 
     private $template; //the template to use
 
-    private $message; //the message array (subject and body)
+    private $message; //the message array  // ['body', 'footer', 'title', 'files']
 
     private $user; //the user the email will be sent from
 
@@ -45,7 +45,7 @@ class TemplateEmail extends Mailable
 
         $company = $this->client->company;
 
-        return $this->from($this->user->email, $this->user->present()->name()) //todo this needs to be fixed to handle the hosted version
+        $message = $this->from($this->user->email, $this->user->present()->name()) //todo this needs to be fixed to handle the hosted version
             ->subject($this->message['subject'])
             ->text('email.template.plain', ['body' => $this->message['body'], 'footer' => $this->message['footer']])
             ->view($template_name, [
@@ -56,5 +56,14 @@ class TemplateEmail extends Mailable
                 'company' => $company
             ]);
 
+
+        //conditionally attach files
+        if($settings->pdf_email_attachment !== false && array_key_exists($this->message['files'])){
+
+            foreach($this->message['files'] as $file)
+                $message->attach($file);
+        }
+
+        return $message;
     }
 }
\ No newline at end of file
diff --git a/app/Models/Activity.php b/app/Models/Activity.php
index d18cd4ca8c80..fe9f62df56cd 100644
--- a/app/Models/Activity.php
+++ b/app/Models/Activity.php
@@ -69,6 +69,7 @@ class Activity extends StaticModel
     const RESTORE_USER=52;
     const MARK_SENT_INVOICE=53;
     const PAID_INVOICE=54;
+    const EMAIL_INVOICE_FAILED=57;
     
     protected $casts = [
         'is_system' => 'boolean',
diff --git a/app/Models/Client.php b/app/Models/Client.php
index 879059d7060f..f79bdb54e862 100644
--- a/app/Models/Client.php
+++ b/app/Models/Client.php
@@ -254,7 +254,7 @@ class Client extends BaseModel
         if($this->group_settings && (property_exists($this->group_settings->settings, $setting) !== false) && (isset($this->group_settings->settings->{$setting}) !== false)){
            return $this->group_settings->settings->{$setting};
         }
-        
+
         /*Company Settings*/
         if((property_exists($this->company->settings, $setting) != false ) && (isset($this->company->settings->{$setting}) !== false) ){
             return $this->company->settings->{$setting};
diff --git a/app/Models/SystemLog.php b/app/Models/SystemLog.php
index 89b5b7240a07..1b7d6ca0a140 100644
--- a/app/Models/SystemLog.php
+++ b/app/Models/SystemLog.php
@@ -17,6 +17,7 @@ class SystemLog extends Model
 {
     /* Category IDs */
     const CATEGORY_GATEWAY_RESPONSE = 1;
+    const CATEGORY_MAIL = 2;
 
     /* Event IDs*/
     const EVENT_PAYMENT_RECONCILIATION_FAILURE = 10;
@@ -26,10 +27,13 @@ class SystemLog extends Model
     const EVENT_GATEWAY_FAILURE = 22;
     const EVENT_GATEWAY_ERROR = 23;
 
+    const EVENT_MAIL_SEND = 30;
+
     /*Type IDs*/
     const TYPE_PAYPAL = 300;
     const TYPE_STRIPE = 301;
     const TYPE_LEDGER = 302;
+    const TYPE_FAILURE = 303;
 
     protected $fillable = [
         'client_id',
diff --git a/app/Models/User.php b/app/Models/User.php
index 681075fb5a2f..25a8219e3a3a 100644
--- a/app/Models/User.php
+++ b/app/Models/User.php
@@ -199,6 +199,11 @@ class User extends Authenticatable implements MustVerifyEmail
         
     }
 
+    public function clients()
+    {
+        return $this->hasMany(Client::class);
+    }
+
     /**
      * Returns a comma separated list of user permissions
      * 
diff --git a/app/Providers/EventServiceProvider.php b/app/Providers/EventServiceProvider.php
index 0e7f4e0ebb4e..de7bc12fb648 100644
--- a/app/Providers/EventServiceProvider.php
+++ b/app/Providers/EventServiceProvider.php
@@ -14,6 +14,7 @@ namespace App\Providers;
 use App\Events\Client\ClientWasCreated;
 use App\Events\Contact\ContactLoggedIn;
 use App\Events\Invoice\InvoiceWasCreated;
+use App\Events\Invoice\InvoiceWasEmailed;
 use App\Events\Invoice\InvoiceWasMarkedSent;
 use App\Events\Invoice\InvoiceWasPaid;
 use App\Events\Invoice\InvoiceWasUpdated;
@@ -29,6 +30,8 @@ use App\Listeners\Invoice\CreateInvoiceActivity;
 use App\Listeners\Invoice\CreateInvoiceHtmlBackup;
 use App\Listeners\Invoice\CreateInvoiceInvitation;
 use App\Listeners\Invoice\CreateInvoicePdf;
+use App\Listeners\Invoice\InvoiceEmailActivity;
+use App\Listeners\Invoice\InvoiceEmailFailedActivity;
 use App\Listeners\Invoice\UpdateInvoiceActivity;
 use App\Listeners\Invoice\UpdateInvoiceInvitations;
 use App\Listeners\Invoice\UpdateInvoicePayment;
@@ -96,7 +99,14 @@ class EventServiceProvider extends ServiceProvider
         ],
         InvoiceWasPaid::class => [
             CreateInvoiceHtmlBackup::class,
-        ]
+        ],
+        InvoiceWasEmailed::class => [
+            InvoiceEmailActivity::class,
+        ],
+        InvoiceWasEmailedAndFailed::class => [
+            InvoiceEmailFailedActivity::class,
+        ],
+        
     ];
 
     /**
diff --git a/app/Repositories/QuoteRepository.php b/app/Repositories/QuoteRepository.php
index 68f22146c88c..a4650819d779 100644
--- a/app/Repositories/QuoteRepository.php
+++ b/app/Repositories/QuoteRepository.php
@@ -13,6 +13,7 @@ namespace App\Repositories;
 
 use App\Factory\QuoteInvitationFactory;
 use App\Helpers\Invoice\InvoiceSum;
+use App\Jobs\Quote\ApplyQuoteNumber;
 use App\Jobs\Quote\CreateQuoteInvitations;
 use App\Models\Client;
 use App\Models\ClientContact;
@@ -99,8 +100,8 @@ class QuoteRepository extends BaseRepository
         $quote->save();
 
         $finished_amount = $quote->amount;
-//todo need answers on this
-//        $quote = ApplyInvoiceNumber::dispatchNow($quote, $quote->client->getMergedSettings());
+
+        $quote = ApplyQuoteNumber::dispatchNow($quote, $quote->client->getMergedSettings());
 
         return $quote->fresh();
 	}
diff --git a/app/Transformers/InvoiceTransformer.php b/app/Transformers/InvoiceTransformer.php
index e6fea3679f8f..0315a523a3b0 100644
--- a/app/Transformers/InvoiceTransformer.php
+++ b/app/Transformers/InvoiceTransformer.php
@@ -96,6 +96,7 @@ class InvoiceTransformer extends EntityTransformer
             'discount' => (float) $invoice->discount,
             'po_number' => $invoice->po_number ?: '',
             'date' => $invoice->date ?: '',
+            'last_sent_date' => $invoice->last_sent_date ?: '',
             'next_send_date' => $invoice->date ?: '',
             'due_date' => $invoice->due_date ?: '',
             'terms' => $invoice->terms ?: '',
@@ -103,7 +104,6 @@ class InvoiceTransformer extends EntityTransformer
             'private_notes' => $invoice->private_notes ?: '',
             'is_deleted' => (bool) $invoice->is_deleted,
             'uses_inclusive_taxes' => (bool) $invoice->uses_inclusive_taxes,
-            'invoice_type_id' => (string) $invoice->invoice_type_id ?: '',
             'tax_name1' => $invoice->tax_name1 ? $invoice->tax_name1 : '',
             'tax_rate1' => (float) $invoice->tax_rate1,
             'tax_name2' => $invoice->tax_name2 ? $invoice->tax_name2 : '',
diff --git a/app/Transformers/QuoteTransformer.php b/app/Transformers/QuoteTransformer.php
index 74ef0e94de4a..fea5b5811af4 100644
--- a/app/Transformers/QuoteTransformer.php
+++ b/app/Transformers/QuoteTransformer.php
@@ -85,6 +85,7 @@ class QuoteTransformer extends EntityTransformer
             'discount' => (float) $quote->discount,
             'po_number' => $quote->po_number ?: '',
             'date' => $quote->date ?: '',
+            'last_sent_date' => $quote->last_sent_date ?: '',
             'next_send_date' => $quote->date ?: '',
             'due_date' => $quote->due_date ?: '',
             'terms' => $quote->terms ?: '',
@@ -92,7 +93,6 @@ class QuoteTransformer extends EntityTransformer
             'private_notes' => $quote->private_notes ?: '',
             'is_deleted' => (bool) $quote->is_deleted,
             'uses_inclusive_taxes' => (bool) $quote->uses_inclusive_taxes,
-            'invoice_type_id' => (string) $quote->invoice_type_id ?: '',
             'tax_name1' => $quote->tax_name1 ? $quote->tax_name1 : '',
             'tax_rate1' => (float) $quote->tax_rate1,
             'tax_name2' => $quote->tax_name2 ? $quote->tax_name2 : '',
diff --git a/app/Utils/Traits/GeneratesCounter.php b/app/Utils/Traits/GeneratesCounter.php
index 6207f517bba7..1883b57686c2 100644
--- a/app/Utils/Traits/GeneratesCounter.php
+++ b/app/Utils/Traits/GeneratesCounter.php
@@ -96,9 +96,44 @@ trait GeneratesCounter
 		return $credit_number;
 	}
 
-	public function getNextQuoteNumber()
+	public function getNextQuoteNumber(Client $client)
 	{
+		//Reset counters if enabled
+		$this->resetCounters($client);
 
+		$used_counter = 'quote_number_counter';
+
+		if($this->hasSharedCounter($client))
+			$used_counter = 'invoice_number_counter';
+
+		//todo handle if we have specific client patterns in the future
+		$pattern = $client->getSetting('quote_number_pattern');
+		//Determine if we are using client_counters
+		if(strpos($pattern, 'clientCounter'))
+		{
+			$counter = $client->settings->{$used_counter};
+			$counter_entity = $client;
+		}
+		elseif(strpos($pattern, 'groupCounter'))
+		{
+			$counter = $client->group_settings->{$used_counter};
+			$counter_entity = $client->group_settings;
+		}
+		else 
+		{
+			$counter = $client->company->settings->{$used_counter};
+			$counter_entity = $client->company;
+		}
+
+		//Return a valid counter
+		$pattern = $client->getSetting('quote_number_pattern');
+		$padding = $client->getSetting('counter_padding');
+		
+		$quote_number = $this->checkEntityNumber(Quote::class, $client, $counter, $padding, $pattern);
+
+		$this->incrementCounter($counter_entity, $used_counter);
+
+		return $quote_number;
 	}
 
 	public function getNextRecurringInvoiceNumber()
@@ -170,9 +205,10 @@ trait GeneratesCounter
 	 * @return     boolean             True if has shared counter, False otherwise.
 	 */
 	public function hasSharedCounter(Client $client) : bool
-	{
-
-		return $client->getSetting('shared_invoice_quote_counter') === TRUE;
+ 	{
+// \Log::error((bool) $client->getSetting('shared_invoice_quote_counter'));
+// \Log::error($client->getSetting('shared_invoice_quote_counter'));
+		return (bool) $client->getSetting('shared_invoice_quote_counter');
 
 	}
 
diff --git a/app/Utils/Traits/InvoiceEmailBuilder.php b/app/Utils/Traits/InvoiceEmailBuilder.php
index 524b8bf5113e..534fd2f4d0b6 100644
--- a/app/Utils/Traits/InvoiceEmailBuilder.php
+++ b/app/Utils/Traits/InvoiceEmailBuilder.php
@@ -65,10 +65,12 @@ trait InvoiceEmailBuilder
 
         }
 
-
         $data['body'] = $this->parseTemplate($body_template, false);
         $data['subject'] = $this->parseTemplate($subject_template, true);
 
+        if($client->getSetting('pdf_email_attachment') !== false)
+            $data['files'][] = $this->pdf_file_path();
+
         return $data;
     }
 
@@ -108,8 +110,11 @@ trait InvoiceEmailBuilder
         {
             return 'template3';
         }
+        else
+            return 'invoice';
+
         //also implement endless reminders here
-        //
+        
            
     }
 
diff --git a/config/ninja.php b/config/ninja.php
index 87c699742027..627f36b8f5be 100644
--- a/config/ninja.php
+++ b/config/ninja.php
@@ -59,7 +59,7 @@ return [
         'stripe' => env('STRIPE_KEYS',''),
         'paypal' => env('PAYPAL_KEYS', ''),
         'travis' => env('TRAVIS', false),
-        'test_email' => env('TEST_EMAIL',''),
+        'test_email' => env('TEST_EMAIL','test@example.com'),
     ],
     'contact' => [
         'email' => env('MAIL_FROM_ADDRESS'),
diff --git a/database/migrations/2014_10_13_000000_create_users_table.php b/database/migrations/2014_10_13_000000_create_users_table.php
index 12622f99f5c4..b70bd73f3092 100644
--- a/database/migrations/2014_10_13_000000_create_users_table.php
+++ b/database/migrations/2014_10_13_000000_create_users_table.php
@@ -452,6 +452,8 @@ class CreateUsersTable extends Migration
 
             $t->string('po_number')->nullable();
             $t->date('date')->nullable();
+            $t->date('last_sent_date')->nullable();
+
             $t->datetime('due_date')->nullable();
 
             $t->boolean('is_deleted')->default(false);
@@ -660,6 +662,8 @@ class CreateUsersTable extends Migration
 
             $t->string('po_number')->nullable();
             $t->date('date')->nullable();
+            $t->date('last_sent_date')->nullable();
+            
             $t->datetime('due_date')->nullable();
             $t->datetime('next_send_date')->nullable();
 
diff --git a/resources/lang/en/texts.php b/resources/lang/en/texts.php
index df52d9a9a90f..c11f4bf11fbb 100644
--- a/resources/lang/en/texts.php
+++ b/resources/lang/en/texts.php
@@ -801,6 +801,7 @@ $LANG = array(
     'activity_54' => ':user reopened ticket :ticket',
     'activity_55' => ':contact replied ticket :ticket',
     'activity_56' => ':user viewed ticket :ticket',
+    'activity_57' => ':invoice failed to send to :client',
 
     'payment' => 'Payment',
     'system' => 'System',
diff --git a/tests/Feature/InvoiceEmailTest.php b/tests/Feature/InvoiceEmailTest.php
index d346d800e2a5..ac4b362e748e 100644
--- a/tests/Feature/InvoiceEmailTest.php
+++ b/tests/Feature/InvoiceEmailTest.php
@@ -55,6 +55,7 @@ class InvoiceEmailTest extends TestCase
         $message_array['title'] = &$message_array['subject'];
         $message_array['footer'] = 'The Footer';
 
+
  //       $template_style = $this->client->getSetting('email_style');
 
         $template_style = 'light';
@@ -62,24 +63,24 @@ class InvoiceEmailTest extends TestCase
 
         $invitations = InvoiceInvitation::whereInvoiceId($this->invoice->id)->get();
 
-        $invitations->each(function($invitation) use($message_array, $template_style) {
+        $invitations->each(function($invitation) use($message_array, $template_styles) {
 
-            $contact = ClientContact::find($invitation->client_contact_id)->first();
+            $contact = $invitation->contact;
 
             if($contact->send_invoice && $contact->email)
             {
                 //there may be template variables left over for the specific contact? need to reparse here
-                
+        
                 //change the runtime config of the mail provider here:
                 
                 //send message
                 Mail::to($contact->email)
-                ->send(new TemplateEmail($message_array, $template_style, $this->user, $this->client));
+                ->send(new TemplateEmail($message_array, $template_style, $this->user, $contact->client));
 
                 //fire any events
                 
 
-                sleep(5);
+                sleep(5);//here to cope with mailtrap time delays
                 
             }
 
diff --git a/tests/Unit/GeneratesCounterTest.php b/tests/Unit/GeneratesCounterTest.php
index a20869742872..f68b16dc9b15 100644
--- a/tests/Unit/GeneratesCounterTest.php
+++ b/tests/Unit/GeneratesCounterTest.php
@@ -50,6 +50,27 @@ class GeneratesCounterTest extends TestCase
         $this->assertFalse($this->hasSharedCounter($this->client));
     }
 
+    public function testHasTrueSharedCounter()
+    {
+        $settings = $this->client->getMergedSettings();
+        $settings->invoice_number_counter = 1;
+        $settings->invoice_number_pattern = '{$year}-{$counter}';
+        $settings->shared_invoice_quote_counter = 1;
+        $this->company->settings = $settings;
+        
+        $this->company->save();
+
+        $this->client->settings = $settings;
+        $this->client->save();
+
+        $gs = $this->client->group_settings;
+        $gs->settings = $settings;
+        $gs->save();
+
+        $this->assertTrue($this->hasSharedCounter($this->client));
+
+    }
+
     public function testInvoiceNumberValue()
     {
 
@@ -63,6 +84,19 @@ class GeneratesCounterTest extends TestCase
 
     }
 
+    public function testQuoteNumberValue()
+    {
+
+        $quote_number = $this->getNextQuoteNumber($this->client);
+
+        $this->assertEquals($quote_number, 0001);
+
+        $quote_number = $this->getNextQuoteNumber($this->client);
+
+        $this->assertEquals($quote_number, '0002');
+
+    }
+
     public function testInvoiceNumberPattern()
     {
         $settings = $this->client->company->settings;
@@ -79,12 +113,58 @@ class GeneratesCounterTest extends TestCase
         $invoice_number = $this->getNextInvoiceNumber($this->client);
         $invoice_number2 = $this->getNextInvoiceNumber($this->client);
 
-        $this->assertEquals($invoice_number, '2019-0001');
-        $this->assertEquals($invoice_number2, '2019-0002');
+        $this->assertEquals($invoice_number, date('Y').'-0001');
+        $this->assertEquals($invoice_number2, date('Y').'-0002');
         $this->assertEquals($this->client->company->settings->invoice_number_counter,3);
        
     }
 
+    public function testQuoteNumberPattern()
+    {
+        $settings = $this->client->company->settings;
+        $settings->quote_number_counter = 1;
+        $settings->quote_number_pattern = '{$year}-{$counter}';
+
+        $this->client->company->settings = $settings;
+        $this->client->company->save();
+
+        $this->client->settings = $settings;
+        $this->client->save();
+        $this->client->fresh();
+
+        $quote_number = $this->getNextQuoteNumber($this->client);
+        $quote_number2 = $this->getNextQuoteNumber($this->client);
+
+        $this->assertEquals($quote_number, date('Y').'-0001');
+        $this->assertEquals($quote_number2, date('Y').'-0002');
+        $this->assertEquals($this->client->company->settings->quote_number_counter,3);
+       
+    }
+
+    public function testQuoteNumberPatternWithSharedCounter()
+    {
+        $settings = $this->client->company->settings;
+        $settings->quote_number_counter = 100;
+        $settings->invoice_number_counter = 1000;
+        $settings->quote_number_pattern = '{$year}-{$counter}';
+        $settings->shared_invoice_quote_counter = true;
+
+        $this->client->company->settings = $settings;
+        $this->client->company->save();
+
+        $gs = $this->client->group_settings;
+        $gs->settings = $settings;
+        $gs->save();
+
+        $quote_number = $this->getNextQuoteNumber($this->client);
+        $quote_number2 = $this->getNextQuoteNumber($this->client);
+
+        $this->assertEquals($quote_number, date('Y').'-1000');
+        $this->assertEquals($quote_number2, date('Y').'-1001');
+        $this->assertEquals($this->client->company->settings->quote_number_counter,100);
+       
+    }
+
     public function testInvoiceClientNumberPattern()
     {
         $settings = $this->company->settings;
@@ -106,10 +186,10 @@ class GeneratesCounterTest extends TestCase
 
         $invoice_number = $this->getNextClientNumber($this->client);
 
-        $this->assertEquals($invoice_number, '2019-0001');
+        $this->assertEquals($invoice_number, date('Y').'-0001');
         
         $invoice_number = $this->getNextClientNumber($this->client);
-		$this->assertEquals($invoice_number, '2019-0002');
+		$this->assertEquals($invoice_number, date('Y').'-0002');
         
        
     }
@@ -266,8 +346,8 @@ class GeneratesCounterTest extends TestCase
         $this->client->setSettingsByEntity(Client::class, $settings);
         $company = Company::find($this->client->company_id);
         $this->assertEquals($company->settings->client_number_counter,1);
-        $this->assertEquals($this->getNextNumber($this->client), '2019-1');
-        $this->assertEquals($this->getNextNumber($this->client), '2019-2');
+        $this->assertEquals($this->getNextNumber($this->client), date('y').'-1');
+        $this->assertEquals($this->getNextNumber($this->client), date('y').'-2');
        
         $company = Company::find($this->client->company_id);
         $this->assertEquals($company->settings->client_number_counter,2);