diff --git a/app/Console/Kernel.php b/app/Console/Kernel.php
index d79c90131d3..523985bb7d0 100644
--- a/app/Console/Kernel.php
+++ b/app/Console/Kernel.php
@@ -11,31 +11,32 @@
 
 namespace App\Console;
 
+use App\Utils\Ninja;
+use App\Models\Account;
+use App\Jobs\Ninja\QueueSize;
+use App\Jobs\Util\DiskCleanup;
+use App\Jobs\Util\ReminderJob;
 use App\Jobs\Cron\AutoBillCron;
-use App\Jobs\Cron\RecurringExpensesCron;
-use App\Jobs\Cron\RecurringInvoicesCron;
+use App\Jobs\Util\VersionCheck;
+use App\Jobs\Ninja\TaskScheduler;
+use App\Jobs\Util\SchedulerCheck;
+use App\Jobs\Ninja\CheckACHStatus;
 use App\Jobs\Cron\SubscriptionCron;
-use App\Jobs\EDocument\EInvoicePullDocs;
-use App\Jobs\Invoice\InvoiceCheckLateWebhook;
+use App\Jobs\Ninja\MailWebhookSync;
+use App\Jobs\Util\QuoteReminderJob;
 use App\Jobs\Ninja\AdjustEmailQuota;
-use App\Jobs\Ninja\BankTransactionSync;
-use App\Jobs\Ninja\CheckACHStatus;
 use App\Jobs\Ninja\CompanySizeCheck;
-use App\Jobs\Ninja\QueueSize;
 use App\Jobs\Ninja\SystemMaintenance;
-use App\Jobs\Ninja\TaskScheduler;
 use App\Jobs\Quote\QuoteCheckExpired;
-use App\Jobs\Subscription\CleanStaleInvoiceOrder;
-use App\Jobs\Util\DiskCleanup;
-use App\Jobs\Util\QuoteReminderJob;
-use App\Jobs\Util\ReminderJob;
-use App\Jobs\Util\SchedulerCheck;
 use App\Jobs\Util\UpdateExchangeRates;
-use App\Jobs\Util\VersionCheck;
-use App\Models\Account;
-use App\PaymentDrivers\Rotessa\Jobs\TransactionReport;
-use App\Utils\Ninja;
+use App\Jobs\Ninja\BankTransactionSync;
+use App\Jobs\Cron\RecurringExpensesCron;
+use App\Jobs\Cron\RecurringInvoicesCron;
+use App\Jobs\EDocument\EInvoicePullDocs;
 use Illuminate\Console\Scheduling\Schedule;
+use App\Jobs\Invoice\InvoiceCheckLateWebhook;
+use App\Jobs\Subscription\CleanStaleInvoiceOrder;
+use App\PaymentDrivers\Rotessa\Jobs\TransactionReport;
 use Illuminate\Foundation\Console\Kernel as ConsoleKernel;
 
 class Kernel extends ConsoleKernel
@@ -121,6 +122,8 @@ protected function schedule(Schedule $schedule)
             /* Checks ACH verification status and updates state to authorize when verified */
             $schedule->job(new CheckACHStatus())->everySixHours()->withoutOverlapping()->name('ach-status-job')->onOneServer();
 
+            $schedule->job(new MailWebhookSync())->everyFourHours(rand(20, 45))->withoutOverlapping()->name('mail-webhook-sync-job')->onOneServer();
+
             $schedule->command('ninja:check-data --database=db-ninja-01')->dailyAt('02:10')->withoutOverlapping()->name('check-data-db-1-job')->onOneServer();
 
             $schedule->command('ninja:check-data --database=db-ninja-02')->dailyAt('02:20')->withoutOverlapping()->name('check-data-db-2-job')->onOneServer();
diff --git a/app/Jobs/Invoice/ZipInvoices.php b/app/Jobs/Invoice/ZipInvoices.php
index ae26fcc90a5..fcf648faea4 100644
--- a/app/Jobs/Invoice/ZipInvoices.php
+++ b/app/Jobs/Invoice/ZipInvoices.php
@@ -73,7 +73,7 @@ public function handle(): void
         $invitation = $this->invoices->first()->invitations->first();
 
         if (!$invitation) {
-            nlog("no Invoice Invitations");
+            nlog("ZipInvoices:: no Invoice Invitations");
             return;
         }
 
@@ -118,7 +118,7 @@ public function handle(): void
             broadcast(new DownloadAvailable($storage_url, $message, $this->user));
 
         } catch (\PhpZip\Exception\ZipException $e) {
-            nlog('could not make zip => '.$e->getMessage());
+            nlog('ZipInvoices:: could not make zip => '.$e->getMessage());
         } finally {
             $zipFile->close();
         }
diff --git a/app/Jobs/Ninja/AdjustEmailQuota.php b/app/Jobs/Ninja/AdjustEmailQuota.php
index 15832893bd4..d12881fe0f0 100644
--- a/app/Jobs/Ninja/AdjustEmailQuota.php
+++ b/app/Jobs/Ninja/AdjustEmailQuota.php
@@ -63,7 +63,7 @@ public function handle()
     public function adjust()
     {
         Account::query()->cursor()->each(function ($account) {
-            nlog("resetting email quota for {$account->key}");
+            // nlog("resetting email quota for {$account->key}");
 
             $email_count = Cache::get("email_quota".$account->key);
 
diff --git a/app/Jobs/Ninja/MailWebhookSync.php b/app/Jobs/Ninja/MailWebhookSync.php
new file mode 100644
index 00000000000..e0bc9ec9e1e
--- /dev/null
+++ b/app/Jobs/Ninja/MailWebhookSync.php
@@ -0,0 +1,174 @@
+<?php
+
+/**
+ * Invoice Ninja (https://invoiceninja.com).
+ *
+ * @link https://github.com/invoiceninja/invoiceninja source repository
+ *
+ * @copyright Copyright (c) 2024. Invoice Ninja LLC (https://invoiceninja.com)
+ *
+ * @license https://www.elastic.co/licensing/elastic-license
+ */
+
+namespace App\Jobs\Ninja;
+
+use App\Utils\Ninja;
+use App\Models\Account;
+use App\Libraries\MultiDB;
+use Illuminate\Bus\Queueable;
+use Illuminate\Support\Facades\Cache;
+use Illuminate\Support\Facades\Redis;
+use Illuminate\Queue\SerializesModels;
+use Turbo124\Beacon\Facades\LightLogs;
+use App\DataMapper\Analytics\EmailCount;
+use Illuminate\Queue\InteractsWithQueue;
+use Illuminate\Contracts\Queue\ShouldQueue;
+use Illuminate\Foundation\Bus\Dispatchable;
+use Illuminate\Queue\Middleware\WithoutOverlapping;
+
+class MailWebhookSync implements ShouldQueue
+{
+    use Dispatchable;
+    use InteractsWithQueue;
+    use Queueable;
+    use SerializesModels;
+
+    public $tries = 1;
+
+    public $deleteWhenMissingModels = true;
+
+    /**
+     * Create a new job instance.
+     *
+     * @return void
+     */
+    public function __construct()
+    {
+        //
+    }
+
+    /**
+     * Execute the job.
+     *
+     * @return void
+     */
+    public function handle()
+    {
+        if (! Ninja::isHosted()) {
+            return;
+        }
+
+        /** Add to the logs any email deliveries that have not been sync'd */
+        foreach (MultiDB::$dbs as $db) {
+            MultiDB::setDB($db);
+
+            $this->scanSentEmails();
+        }
+    }
+
+    private function scanSentEmails()
+    {
+
+        $query = \App\Models\InvoiceInvitation::whereNotNull('message_id')
+        ->whereNull('email_status')
+        ->whereHas('company', function ($q) {
+            $q->where('settings->email_sending_method', 'default');
+        });
+
+        $this->runIterator($query);
+
+
+        $query = \App\Models\QuoteInvitation::whereNotNull('message_id')
+        ->whereNull('email_status')
+        ->whereHas('company', function ($q) {
+            $q->where('settings->email_sending_method', 'default');
+        });
+
+        $this->runIterator($query);
+
+
+        $query = \App\Models\RecurringInvoiceInvitation::whereNotNull('message_id')
+        ->whereNull('email_status')
+        ->whereHas('company', function ($q) {
+            $q->where('settings->email_sending_method', 'default');
+        });
+
+        $this->runIterator($query);
+
+
+        $query = \App\Models\CreditInvitation::whereNotNull('message_id')
+        ->whereNull('email_status')
+        ->whereHas('company', function ($q) {
+            $q->where('settings->email_sending_method', 'default');
+        });
+
+        $this->runIterator($query);
+
+
+        $query = \App\Models\PurchaseOrderInvitation::whereNotNull('message_id')
+        ->whereNull('email_status')
+        ->whereHas('company', function ($q) {
+            $q->where('settings->email_sending_method', 'default');
+        });
+
+        $this->runIterator($query);
+
+    }
+
+    private function runIterator($query)
+    {
+        $query->where('created_at' , '<', now()->subHours(1))
+        ->each(function ($invite) {
+
+            $postmark = new \Postmark\PostmarkClient(config('services.postmark.token'));
+
+            try {
+                $messageDetail = $postmark->getOutboundMessageDetails($invite->message_id);
+            } catch (\Throwable $th) {
+                $postmark = new \Postmark\PostmarkClient(config('services.postmark-outlook.token'));
+                $messageDetail = $postmark->getOutboundMessageDetails($invite->message_id);
+            }
+
+            try {
+
+                if (!$messageDetail) {
+                    return true;
+                }
+
+                $data = [
+                    'RecordType' => 'Delivery',
+                    'ServerID' => 23,
+                    'MessageStream' => 'outbound',
+                    'MessageID' => $invite->message_id,
+                    'Recipient' => collect($messageDetail->recipients)->first(),
+                    'Tag' => $invite->company->company_key,
+                    'DeliveredAt' => '2025-01-01T16:34:52Z',
+                    'Metadata' => [
+
+                    ]
+                ];
+
+                (new \App\Jobs\PostMark\ProcessPostmarkWebhook($data))->handle();
+
+                $invite->sent_date = now();
+                $invite->save();
+
+            } catch (\Throwable $th) {
+                nlog("MailWebhookSync:: {$th->getMessage()}");
+            }
+
+        });
+
+    }
+
+    public function middleware()
+    {
+        return [new WithoutOverlapping('mail-webhook-sync')];
+    }
+
+    public function failed($exception)
+    {
+        nlog("MailWebhookSync:: Exception:: => ".$exception->getMessage());
+        config(['queue.failed.driver' => null]);
+    }
+}
diff --git a/app/Listeners/Mail/MailSentListener.php b/app/Listeners/Mail/MailSentListener.php
index a37aba40c0b..51405a50780 100644
--- a/app/Listeners/Mail/MailSentListener.php
+++ b/app/Listeners/Mail/MailSentListener.php
@@ -61,6 +61,7 @@ public function handle(MessageSent $event)
                     return;
                 }
 
+                $invitation->sent_date = now();
                 $invitation->message_id = str_replace(["<",">"], "", $message_id);
                 $invitation->save();
             }