diff --git a/VKAPI/Handlers/Audio.php b/VKAPI/Handlers/Audio.php
index b25285c0..9f6d3003 100644
--- a/VKAPI/Handlers/Audio.php
+++ b/VKAPI/Handlers/Audio.php
@@ -462,7 +462,11 @@ final class Audio extends VKAPIRequestHandler
         else if(!$audio->canBeViewedBy($this->getUser()))
             $this->fail(201, "Access denied to audio(owner=$owner_id, vid=$audio_id)");
 
-        $audio->add($to);
+        try {
+            $audio->add($to);
+        } catch(\OverflowException $ex) {
+            $this->fail(300, "Album is full");
+        }
 
         return $audio->getPrettyId();
     }
diff --git a/Web/Models/Entities/Audio.php b/Web/Models/Entities/Audio.php
index f758692d..73ffb8f4 100644
--- a/Web/Models/Entities/Audio.php
+++ b/Web/Models/Entities/Audio.php
@@ -266,8 +266,13 @@ class Audio extends Media
         if($this->isInLibraryOf($entity))
             return false;
 
-        DatabaseConnection::i()->getContext()->table("audio_relations")->insert([
-            "entity" => $entity->getId() * ($entity instanceof Club ? -1 : 1),
+        $entityId  = $entity->getId() * ($entity instanceof Club ? -1 : 1);
+        $audioRels = DatabaseConnection::i()->getContext()->table("audio_relations");
+        if(sizeof($audioRels->where("entity", $entityId)) > 65536)
+            throw new \OverflowException("Can't have more than 65536 audios in a playlist");
+
+        $audioRels->insert([
+            "entity" => $entityId,
             "audio"  => $this->getId(),
         ]);