diff --git a/src/Discord/Builders/MessageBuilder.php b/src/Discord/Builders/MessageBuilder.php
index 1b7321e25..ffa263c22 100644
--- a/src/Discord/Builders/MessageBuilder.php
+++ b/src/Discord/Builders/MessageBuilder.php
@@ -69,7 +69,7 @@ class MessageBuilder implements JsonSerializable
 
     /**
      * Attachments to send with this message.
-     * 
+     *
      * @var Attachment[]
      */
     private $attachments = [];
diff --git a/src/Discord/Helpers/Collection.php b/src/Discord/Helpers/Collection.php
index 50733ce61..5ed35c09a 100644
--- a/src/Discord/Helpers/Collection.php
+++ b/src/Discord/Helpers/Collection.php
@@ -228,6 +228,24 @@ public function first()
         return null;
     }
 
+    /**
+     * Returns the last element of the collection.
+     *
+     * @return mixed
+     */
+    public function last()
+    {
+        $last = end($this->items);
+
+        if ($last !== false) {
+            reset($this->items);
+
+            return $last;
+        }
+
+        return null;
+    }
+
     /**
      * If the collection has an offset.
      *
diff --git a/src/Discord/Parts/Channel/Channel.php b/src/Discord/Parts/Channel/Channel.php
index 5bbb23179..b0b435ca5 100644
--- a/src/Discord/Parts/Channel/Channel.php
+++ b/src/Discord/Parts/Channel/Channel.php
@@ -38,6 +38,7 @@
 use Symfony\Component\OptionsResolver\OptionsResolver;
 use Traversable;
 
+use function Discord\getSnowflakeTimestamp;
 use function React\Promise\all;
 use function React\Promise\reject;
 use function React\Promise\resolve;
@@ -546,45 +547,35 @@ public function deleteMessages($messages, ?string $reason = null): ExtendedPromi
             return reject(new \UnexpectedValueException('$messages must be an array or implement Traversable.'));
         }
 
-        $count = count($messages);
-
-        if ($count == 0) {
-            return resolve();
-        } elseif ($count == 1 || $this->is_private) {
-            foreach ($messages as $message) {
-                if ($message instanceof Message ||
-                    $message = $this->messages->get('id', $message)
-                ) {
-                    return $message->delete();
-                }
+        $headers = $promises = $messagesBulk = $messagesSingle = [];
+        if (isset($reason)) {
+            $headers['X-Audit-Log-Reason'] = $reason;
+        }
 
-                return $this->http->delete(Endpoint::bind(Endpoint::CHANNEL_MESSAGE, $this->id, $message));
+        foreach ($messages as $message) {
+            if ($message instanceof Message) {
+                $message = $message->id;
             }
-        } else {
-            $messageID = [];
 
-            foreach ($messages as $message) {
-                if ($message instanceof Message) {
-                    $messageID[] = $message->id;
-                } else {
-                    $messageID[] = $message;
-                }
+            if ($this->is_private || getSnowflakeTimestamp($message) < time() - 1209600) {
+                $messagesSingle[] = $message;
+            } else {
+                $messagesBulk[] = $message;
             }
+        }
 
-            $promises = [];
-
-            $headers = [];
-            if (isset($reason)) {
-                $headers['X-Audit-Log-Reason'] = $reason;
-            }
+        while (count($messagesBulk) > 1) {
+            $promises[] = $this->http->post(Endpoint::bind(Endpoint::CHANNEL_MESSAGES_BULK_DELETE, $this->id), ['messages' => array_slice($messagesBulk, 0, 100)], $headers);
+            $messagesBulk = array_slice($messagesBulk, 100);
+        }
 
-            while (! empty($messageID)) {
-                $promises[] = $this->http->post(Endpoint::bind(Endpoint::CHANNEL_MESSAGES_BULK_DELETE, $this->id), ['messages' => array_slice($messageID, 0, 100)], $headers);
-                $messageID = array_slice($messageID, 100);
-            }
+        $messagesSingle = array_merge($messagesSingle, $messagesBulk);
 
-            return all($promises);
+        foreach ($messagesSingle as $message) {
+            $promises[] = $this->http->delete(Endpoint::bind(Endpoint::CHANNEL_MESSAGE, $this->id, $message));
         }
+
+        return all($promises);
     }
 
     /**
diff --git a/src/Discord/Parts/Channel/Message.php b/src/Discord/Parts/Channel/Message.php
index 904535129..f0a0b34f6 100644
--- a/src/Discord/Parts/Channel/Message.php
+++ b/src/Discord/Parts/Channel/Message.php
@@ -44,7 +44,7 @@
  * @property string|null                 $guild_id                               The unique identifier of the guild that the channel the message was sent in belongs to.
  * @property Guild|null                  $guild                                  The guild that the message was sent in.
  * @property User|null                   $author                                 The author of the message. Will be a webhook if sent from one.
- * @property string                      $user_id                                The user id of the author.
+ * @property string|null                 $user_id                                The user id of the author.
  * @property Member|null                 $member                                 The member that sent this message, or null if it was in a private message.
  * @property string                      $content                                The content of the message if it is a normal message.
  * @property Carbon                      $timestamp                              A timestamp of when the message was sent.
diff --git a/src/Discord/Voice/VoiceClient.php b/src/Discord/Voice/VoiceClient.php
index 517ad9962..7a7e8d43a 100644
--- a/src/Discord/Voice/VoiceClient.php
+++ b/src/Discord/Voice/VoiceClient.php
@@ -319,7 +319,7 @@ class VoiceClient extends EventEmitter
     protected $version = 4;
 
     /**
-     * The Config for DNS Resolver
+     * The Config for DNS Resolver.
      *
      * @var string|\React\Dns\Config\Config
      */