diff --git a/app/Api/V1/Requests/Webhook/CreateRequest.php b/app/Api/V1/Requests/Webhook/CreateRequest.php
index e0284f1667..8ec557bd24 100644
--- a/app/Api/V1/Requests/Webhook/CreateRequest.php
+++ b/app/Api/V1/Requests/Webhook/CreateRequest.php
@@ -73,7 +73,7 @@ class CreateRequest extends FormRequest
         $deliveries = implode(',', array_values(config('firefly.webhooks.deliveries')));
 
         return [
-            'title'    => 'between:1,512',
+            'title'    => 'required|between:1,512|uniqueObjectForUser:webhooks,title',
             'active'   => [new IsBoolean],
             'trigger'  => sprintf('required|in:%s', $triggers),
             'response' => sprintf('required|in:%s', $responses),
diff --git a/app/Api/V1/Requests/Webhook/UpdateRequest.php b/app/Api/V1/Requests/Webhook/UpdateRequest.php
index 26a4a3f52c..8abd735841 100644
--- a/app/Api/V1/Requests/Webhook/UpdateRequest.php
+++ b/app/Api/V1/Requests/Webhook/UpdateRequest.php
@@ -57,6 +57,7 @@ class UpdateRequest extends FormRequest
         $return['trigger']  = $triggers[$return['trigger']] ?? 0;
         $return['response'] = $responses[$return['response']] ?? 0;
         $return['delivery'] = $deliveries[$return['delivery']] ?? 0;
+        $return['secret']   = null !== $this->get('secret');
 
         return $return;
     }
@@ -74,7 +75,7 @@ class UpdateRequest extends FormRequest
         $webhook    = $this->route()->parameter('webhook');
 
         return [
-            'title'    => 'between:1,512',
+            'title'    => sprintf('between:1,512|uniqueObjectForUser:webhooks,title,%d', $webhook->id),
             'active'   => [new IsBoolean],
             'trigger'  => sprintf('required|in:%s', $triggers),
             'response' => sprintf('required|in:%s', $responses),
diff --git a/app/Generator/Webhook/StandardMessageGenerator.php b/app/Generator/Webhook/StandardMessageGenerator.php
index 17e7254e57..4031a5b705 100644
--- a/app/Generator/Webhook/StandardMessageGenerator.php
+++ b/app/Generator/Webhook/StandardMessageGenerator.php
@@ -53,6 +53,7 @@ class StandardMessageGenerator implements MessageGeneratorInterface
      */
     public function generateMessages(): void
     {
+        Log::debug(__METHOD__);
         // get the webhooks:
         $this->webhooks = $this->getWebhooks();
 
@@ -105,6 +106,7 @@ class StandardMessageGenerator implements MessageGeneratorInterface
         foreach ($this->webhooks as $webhook) {
             $this->runWebhook($webhook);
         }
+        Log::debug('Done with StandardMessageGenerator::run');
     }
 
     /**
diff --git a/app/Handlers/Events/StoredGroupEventHandler.php b/app/Handlers/Events/StoredGroupEventHandler.php
index a0eee4051a..1cb6dc1ef1 100644
--- a/app/Handlers/Events/StoredGroupEventHandler.php
+++ b/app/Handlers/Events/StoredGroupEventHandler.php
@@ -86,7 +86,7 @@ class StoredGroupEventHandler
      */
     public function triggerWebhooks(StoredTransactionGroup $storedGroupEvent): void
     {
-        Log::debug('StoredTransactionGroup:triggerWebhooks');
+        Log::debug(__METHOD__);
         $group    = $storedGroupEvent->transactionGroup;
         $user     = $group->user;
         /** @var MessageGeneratorInterface $engine */
diff --git a/app/Handlers/Events/WebhookEventHandler.php b/app/Handlers/Events/WebhookEventHandler.php
index 08c2218568..f6460dac1f 100644
--- a/app/Handlers/Events/WebhookEventHandler.php
+++ b/app/Handlers/Events/WebhookEventHandler.php
@@ -37,7 +37,7 @@ class WebhookEventHandler
      */
     public function sendWebhookMessages(): void
     {
-        // kick offf the job!
+        // kick off the job!
         $messages = WebhookMessage
             ::where('webhook_messages.sent', 0)
             ->where('webhook_messages.errored', 0)
diff --git a/app/Helpers/Webhook/Sha3SignatureGenerator.php b/app/Helpers/Webhook/Sha3SignatureGenerator.php
index 78346f9fd1..43d474622d 100644
--- a/app/Helpers/Webhook/Sha3SignatureGenerator.php
+++ b/app/Helpers/Webhook/Sha3SignatureGenerator.php
@@ -30,7 +30,7 @@ use JsonException;
  */
 class Sha3SignatureGenerator implements SignatureGeneratorInterface
 {
-    private int $version = 0;
+    private int $version = 1;
 
     /**
      * @inheritDoc
diff --git a/app/Http/Controllers/HomeController.php b/app/Http/Controllers/HomeController.php
index 4146d5972c..6423ff0491 100644
--- a/app/Http/Controllers/HomeController.php
+++ b/app/Http/Controllers/HomeController.php
@@ -110,6 +110,7 @@ class HomeController extends Controller
      */
     public function index(AccountRepositoryInterface $repository)
     {
+        var_dump(\Str::random(24));
         $types = config('firefly.accountTypesByIdentifier.asset');
         $count = $repository->count($types);
         Log::channel('audit')->info('User visits homepage.');
diff --git a/app/Jobs/SendWebhookMessage.php b/app/Jobs/SendWebhookMessage.php
index a36d7a5cff..3aa23faefa 100644
--- a/app/Jobs/SendWebhookMessage.php
+++ b/app/Jobs/SendWebhookMessage.php
@@ -23,7 +23,7 @@ class SendWebhookMessage implements ShouldQueue
     /**
      * Create a new job instance.
      *
-     * @return void
+     * @param WebhookMessage $message
      */
     public function __construct(WebhookMessage $message)
     {
diff --git a/app/Models/Webhook.php b/app/Models/Webhook.php
index 3ca961801c..2281de76c5 100644
--- a/app/Models/Webhook.php
+++ b/app/Models/Webhook.php
@@ -82,7 +82,7 @@ class Webhook extends Model
     // delivery
     public const DELIVERY_JSON = 300;
 
-    protected $fillable = ['active', 'trigger', 'response', 'delivery', 'user_id', 'url'];
+    protected $fillable = ['active', 'trigger', 'response', 'delivery', 'user_id', 'url', 'title', 'secret'];
 
     protected $casts
         = [
diff --git a/app/Repositories/Webhook/WebhookRepository.php b/app/Repositories/Webhook/WebhookRepository.php
index 6837e4fbb4..aa8690c1fc 100644
--- a/app/Repositories/Webhook/WebhookRepository.php
+++ b/app/Repositories/Webhook/WebhookRepository.php
@@ -25,6 +25,7 @@ namespace FireflyIII\Repositories\Webhook;
 use FireflyIII\Models\Webhook;
 use FireflyIII\User;
 use Illuminate\Support\Collection;
+use Str;
 
 /**
  * Class WebhookRepository
@@ -54,6 +55,7 @@ class WebhookRepository implements WebhookRepositoryInterface
      */
     public function store(array $data): Webhook
     {
+        $secret   = $random = Str::random(24);
         $fullData = [
             'user_id'  => $this->user->id,
             'active'   => $data['active'] ?? false,
@@ -61,6 +63,7 @@ class WebhookRepository implements WebhookRepositoryInterface
             'trigger'  => $data['trigger'],
             'response' => $data['response'],
             'delivery' => $data['delivery'],
+            'secret'   => $secret,
             'url'      => $data['url'],
         ];
 
@@ -77,6 +80,12 @@ class WebhookRepository implements WebhookRepositoryInterface
         $webhook->response = $data['response'] ?? $webhook->response;
         $webhook->delivery = $data['delivery'] ?? $webhook->delivery;
         $webhook->url      = $data['url'] ?? $webhook->url;
+
+        if (array_key_exists('secret', $data) && null !== $data['secret']) {
+            $secret          = $random = Str::random(24);
+            $webhook->secret = $secret;
+        }
+
         $webhook->save();
 
         return $webhook;
diff --git a/app/Services/Webhook/StandardWebhookSender.php b/app/Services/Webhook/StandardWebhookSender.php
index 7739c14e7b..544942b364 100644
--- a/app/Services/Webhook/StandardWebhookSender.php
+++ b/app/Services/Webhook/StandardWebhookSender.php
@@ -22,7 +22,9 @@ declare(strict_types=1);
 
 namespace FireflyIII\Services\Webhook;
 
+use Exception;
 use FireflyIII\Helpers\Webhook\SignatureGeneratorInterface;
+use FireflyIII\Models\WebhookAttempt;
 use FireflyIII\Models\WebhookMessage;
 use GuzzleHttp\Client;
 use GuzzleHttp\Exception\ClientException;
@@ -68,12 +70,17 @@ class StandardWebhookSender implements WebhookSenderInterface
         try {
             $json = json_encode($this->message->message, JSON_THROW_ON_ERROR);
         } catch (JsonException $e) {
-            // TODO throw Firefly Exception
-            //            $attempt = new WebhookAttempt;
-            //            $attempt->webhookMessage()->associate($this->message);
-            //            $attempt->status_code = 0;
-            //            $attempt->logs        = sprintf('Json error: %s', $e->getMessage());
-            //            $attempt->save();
+            Log::error('Did not send message because of a JSON error.');
+            Log::error($e->getMessage());
+            Log::error($e->getTraceAsString());
+            $attempt = new WebhookAttempt;
+            $attempt->webhookMessage()->associate($this->message);
+            $attempt->status_code = 0;
+            $attempt->logs        = sprintf('Json error: %s', $e->getMessage());
+            $attempt->save();
+            $this->message->errored = true;
+            $this->message->sent    = false;
+            $this->message->save();
 
             return;
         }
@@ -89,7 +96,6 @@ class StandardWebhookSender implements WebhookSenderInterface
             ],
         ];
         $client  = new Client;
-        //$logs    = $this->message->logs ?? [];
         try {
             $res                 = $client->request('POST', $this->message->webhook->url, $options);
             $this->message->sent = true;
@@ -99,22 +105,13 @@ class StandardWebhookSender implements WebhookSenderInterface
             //$logs[]           = sprintf('%s: %s', date('Y-m-d H:i:s'), $e->getMessage());
             $this->message->errored = true;
             $this->message->sent    = false;
+            $this->message->save();
+            return;
         }
         $this->message->save();
 
-        //        $attempt = new WebhookAttempt;
-        //        $attempt->webhookMessage()->associate($this->message);
-        //        $attempt->status_code = $res->getStatusCode();
-        //        $attempt->logs        = '';
-        //        $attempt->response    = (string)$res->getBody();
-        //        $attempt->save();
-
         Log::debug(sprintf('Webhook message #%d was sent. Status code %d', $this->message->id, $res->getStatusCode()));
         Log::debug(sprintf('Webhook request body size: %d bytes', strlen($json)));
         Log::debug(sprintf('Response body: %s', $res->getBody()));
-
-        //$sender
-
-        //$this->sendMessageV0($this->message);
     }
 }
diff --git a/app/Transformers/WebhookTransformer.php b/app/Transformers/WebhookTransformer.php
index ea99a44380..8ee39231e3 100644
--- a/app/Transformers/WebhookTransformer.php
+++ b/app/Transformers/WebhookTransformer.php
@@ -55,6 +55,7 @@ class WebhookTransformer extends AbstractTransformer
             'updated_at' => $webhook->updated_at->toAtomString(),
             'active'     => $webhook->active,
             'title'      => $webhook->title,
+            'secret'     => $webhook->secret,
             'trigger'    => $this->getEnum($webhook->trigger),
             'response'   => $this->getEnum($webhook->response),
             'delivery'   => $this->getEnum($webhook->delivery),
diff --git a/app/Validation/FireflyValidator.php b/app/Validation/FireflyValidator.php
index 89b0b59cc5..67de90d5ee 100644
--- a/app/Validation/FireflyValidator.php
+++ b/app/Validation/FireflyValidator.php
@@ -655,6 +655,7 @@ class FireflyValidator extends Validator
                                 ->where('id', '!=', $existingId)
                                 ->where('url', $url)->count();
         }
+
         return false;
     }