diff --git a/src/app/Policy/Greylist/Request.php b/src/app/Policy/Greylist/Request.php
index 6ceba954..148b5d9b 100644
--- a/src/app/Policy/Greylist/Request.php
+++ b/src/app/Policy/Greylist/Request.php
@@ -1,278 +1,301 @@
 <?php
 
 namespace App\Policy\Greylist;
 
 use Illuminate\Support\Facades\DB;
 
 class Request
 {
     protected $header;
     protected $netID;
     protected $netType;
     protected $recipientHash;
     protected $recipientID = null;
     protected $recipientType = null;
     protected $sender;
     protected $senderLocal = 'unknown';
     protected $senderDomain = 'unknown';
     protected $timestamp;
     protected $whitelist;
     protected $request = [];
 
     public function __construct($request)
     {
         $this->request = $request;
 
         if (array_key_exists('timestamp', $this->request)) {
             $this->timestamp = \Carbon\Carbon::parse($this->request['timestamp']);
         } else {
             $this->timestamp = \Carbon\Carbon::now();
         }
     }
 
     public function headerGreylist()
     {
         if ($this->whitelist) {
             if ($this->whitelist->sender_local) {
                 return sprintf(
                     "Received-Greylist: sender %s whitelisted since %s",
                     $this->sender,
                     $this->whitelist->created_at->toDateString()
                 );
             }
 
             return sprintf(
                 "Received-Greylist: domain %s from %s whitelisted since %s (UTC)",
                 $this->senderDomain,
                 $this->request['client_address'],
                 $this->whitelist->created_at->toDateTimeString()
             );
         }
 
         $connect = $this->findConnectsCollection()->orderBy('created_at')->first();
 
         if ($connect) {
             return sprintf(
                 "Received-Greylist: greylisted from %s until %s.",
                 $connect->created_at,
                 $this->timestamp
             );
         }
 
         return "Received-Greylist: no opinion here";
     }
 
     public function shouldDefer()
     {
         list($this->netID, $this->netType) = \App\Utils::getNetFromAddress($this->request['client_address']);
 
         if (!$this->netID) {
             return true;
         }
 
         $recipient = $this->recipientFromRequest();
 
         $this->sender = $this->senderFromRequest();
 
         if (strpos($this->sender, '@') !== false) {
             list($this->senderLocal, $this->senderDomain) = explode('@', $this->sender);
         }
 
         if (strlen($this->senderLocal) > 255) {
             $this->senderLocal = substr($this->senderLocal, 0, 255);
         }
 
         $entry = $this->findConnectsCollectionRecent()->orderBy('updated_at')->first();
 
         if (!$entry) {
             // purge all entries to avoid a unique constraint violation.
             $this->findConnectsCollection()->delete();
 
             $entry = Connect::create(
                 [
                     'sender_local' => $this->senderLocal,
                     'sender_domain' => $this->senderDomain,
                     'net_id' => $this->netID,
                     'net_type' => $this->netType,
                     'recipient_hash' => $this->recipientHash,
                     'recipient_id' => $this->recipientID,
                     'recipient_type' => $this->recipientType,
                     'connect_count' => 1,
                     'created_at' => $this->timestamp,
                     'updated_at' => $this->timestamp
                 ]
             );
         }
 
         // See if the recipient opted-out of the feature
         $enabled = true;
         if ($recipient) {
             $enabled = $recipient->getSetting('greylist_enabled') !== 'false';
         }
 
         // FIXME: Shouldn't we bail-out (return early) if there's no $recipient?
 
         // the following block is to maintain statistics and state ...
-        $entries = Connect::where(
-            [
-                'sender_domain' => $this->senderDomain,
-                'net_id' => $this->netID,
-                'net_type' => $this->netType
-            ]
-        )
-            ->whereDate('updated_at', '>=', $this->timestamp->copy()->subDays(7));
 
         // determine if the sender domain is a whitelist from this network
         $this->whitelist = Whitelist::where(
             [
                 'sender_domain' => $this->senderDomain,
                 'net_id' => $this->netID,
                 'net_type' => $this->netType
             ]
         )->first();
 
+        $cutoffDate = $this->timestamp->copy()->subDays(7);
+
         if ($this->whitelist) {
             if ($this->whitelist->updated_at < $this->timestamp->copy()->subMonthsWithoutOverflow(1)) {
                 $this->whitelist->delete();
             } else {
                 $this->whitelist->updated_at = $this->timestamp;
                 $this->whitelist->save(['timestamps' => false]);
 
-                $entries->update(
+                Connect::where(
                     [
-                        'greylisting' => false,
-                        'updated_at' => $this->timestamp
+                        'sender_domain' => $this->senderDomain,
+                        'net_id' => $this->netID,
+                        'net_type' => $this->netType,
+                        'greylisting' => true
                     ]
-                );
+                )
+                    ->whereDate('updated_at', '>=', $cutoffDate)
+                    ->update(
+                        [
+                            'greylisting' => false,
+                            'updated_at' => $this->timestamp
+                        ]
+                    );
 
                 return false;
             }
         } else {
-            if ($entries->count() >= 5) {
+            $count = Connect::where(
+                [
+                    'sender_domain' => $this->senderDomain,
+                    'net_id' => $this->netID,
+                    'net_type' => $this->netType
+                ]
+            )
+                ->whereDate('updated_at', '>=', $cutoffDate)
+                ->limit(5)->count();
+
+            // Automatically create a whitelist if we have at least 5 messages from the sender
+            if ($count >= 5) {
                 $this->whitelist = Whitelist::create(
                     [
                         'sender_domain' => $this->senderDomain,
                         'net_id' => $this->netID,
                         'net_type' => $this->netType,
                         'created_at' => $this->timestamp,
                         'updated_at' => $this->timestamp
                     ]
                 );
 
-                $entries->update(
+                Connect::where(
                     [
-                        'greylisting' => false,
-                        'updated_at' => $this->timestamp
+                        'sender_domain' => $this->senderDomain,
+                        'net_id' => $this->netID,
+                        'net_type' => $this->netType,
+                        'greylisting' => true
                     ]
-                );
+                )
+                    ->whereDate('updated_at', '>=', $cutoffDate)
+                    ->update(
+                        [
+                            'greylisting' => false,
+                            'updated_at' => $this->timestamp
+                        ]
+                    );
             }
         }
 
         // TODO: determine if the sender (individual) is a whitelist
 
         // TODO: determine if the sender is a penpal of any of the recipients. First recipient wins.
 
         if (!$enabled) {
             return false;
         }
 
         // determine if the sender, net and recipient combination has existed before, for each recipient
         // any one recipient matching should supersede the other recipients not having matched
         $connect = Connect::where(
             [
                 'sender_local' => $this->senderLocal,
                 'sender_domain' => $this->senderDomain,
                 'recipient_hash' => $this->recipientHash,
                 'net_id' => $this->netID,
                 'net_type' => $this->netType,
             ]
         )
             ->whereDate('updated_at', '>=', $this->timestamp->copy()->subMonthsWithoutOverflow(1))
             ->orderBy('updated_at')
             ->first();
 
         $deferIfPermit = true;
 
         if ($connect) {
             $connect->connect_count += 1;
 
             // TODO: The period of time for which the greylisting persists is configurable.
             if ($connect->created_at < $this->timestamp->copy()->subMinutes(5)) {
                 $deferIfPermit = false;
 
                 $connect->greylisting = false;
             }
 
             $connect->save();
         } else {
             Connect::create(
                 [
                     'sender_local' => $this->senderLocal,
                     'sender_domain' => $this->senderDomain,
                     'net_id' => $this->netID,
                     'net_type' => $this->netType,
                     'recipient_hash' => $this->recipientHash,
                     'recipient_id' => $this->recipientID,
                     'recipient_type' => $this->recipientType,
                     'created_at' => $this->timestamp,
                     'updated_at' => $this->timestamp
                 ]
             );
         }
 
         return $deferIfPermit;
     }
 
     private function findConnectsCollection()
     {
         $collection = Connect::where(
             [
                 'sender_local' => $this->senderLocal,
                 'sender_domain' => $this->senderDomain,
                 'recipient_hash' => $this->recipientHash,
                 'net_id' => $this->netID,
                 'net_type' => $this->netType,
             ]
         );
 
         return $collection;
     }
 
     private function findConnectsCollectionRecent()
     {
         return $this->findConnectsCollection()
             ->where('updated_at', '>=', $this->timestamp->copy()->subDays(7));
     }
 
     private function recipientFromRequest()
     {
         $recipients = \App\Utils::findObjectsByRecipientAddress($this->request['recipient']);
 
         if (sizeof($recipients) > 1) {
             \Log::warning(
                 "Only taking the first recipient from the request for {$this->request['recipient']}"
             );
         }
 
         if (count($recipients) >= 1) {
             foreach ($recipients as $recipient) {
                 if ($recipient) {
                     $this->recipientID = $recipient->id;
                     $this->recipientType = get_class($recipient);
                     break;
                 }
             }
         } else {
             $recipient = null;
         }
 
         $this->recipientHash = hash('sha256', \App\Utils::normalizeAddress($this->request['recipient']));
 
         return $recipient;
     }
 
     public function senderFromRequest()
     {
         return \App\Utils::normalizeAddress($this->request['sender']);
     }
 }