diff --git a/lib/Entity/Playlist.php b/lib/Entity/Playlist.php
index 8ae2464c5b..da360b2726 100644
--- a/lib/Entity/Playlist.php
+++ b/lib/Entity/Playlist.php
@@ -2,7 +2,7 @@
 /*
  * Copyright (C) 2023 Xibo Signage Ltd
  *
- * Xibo - Digital Signage - http://www.xibo.org.uk
+ * Xibo - Digital Signage - https://xibosignage.com
  *
  * This file is part of Xibo.
  *
@@ -458,10 +458,9 @@ public function assignWidget($widget, $displayOrder = null)
                     // This widget is >= the display order and therefore needs to be moved down one position.
                     $existingWidget->displayOrder = $existingWidget->displayOrder + 1;
                 }
-
-                // Set the incoming widget to the requested display order.
-                $widget->displayOrder = $displayOrder;
             }
+            // Set the incoming widget to the requested display order.
+            $widget->displayOrder = $displayOrder;
         } else {
             // Take the next available one
             $widget->displayOrder = count($this->widgets) + 1;
@@ -579,7 +578,8 @@ public function load($loadOptions = [])
             'loadPermissions' => true,
             'loadWidgets' => true,
             'loadTags' => true,
-            'loadActions' => true
+            'loadActions' => true,
+            'checkDisplayOrder' => false,
         ], $loadOptions);
 
         $this->getLog()->debug('Load Playlist with ' . json_encode($options));
@@ -601,6 +601,27 @@ public function load($loadOptions = [])
                 $widget->load($options['loadActions']);
                 $this->widgets[] = $widget;
             }
+
+            // for dynamic sync task
+            // make sure we have correct displayOrder on all existing Widgets here.
+            if ($this->isDynamic === 1 && $options['checkDisplayOrder']) {
+                // Sort the widgets by their display order
+                usort($this->widgets, function ($a, $b) {
+                    /**
+                     * @var Widget $a
+                     * @var Widget $b
+                     */
+                    return $a->displayOrder - $b->displayOrder;
+                });
+
+                $i = 0;
+                foreach ($this->widgets as $widget) {
+                    /* @var Widget $widget */
+                    $i++;
+                    // Assert the displayOrder
+                    $widget->displayOrder = $i;
+                }
+            }
         }
 
         $this->hash = $this->hash();
diff --git a/lib/XTR/DynamicPlaylistSyncTask.php b/lib/XTR/DynamicPlaylistSyncTask.php
index 446c6e9a6d..29a4a53784 100644
--- a/lib/XTR/DynamicPlaylistSyncTask.php
+++ b/lib/XTR/DynamicPlaylistSyncTask.php
@@ -1,8 +1,8 @@
 <?php
-/**
- * Copyright (C) 2020 Xibo Signage Ltd
+/*
+ * Copyright (C) 2023 Xibo Signage Ltd
  *
- * Xibo - Digital Signage - http://www.xibo.org.uk
+ * Xibo - Digital Signage - https://xibosignage.com
  *
  * This file is part of Xibo.
  *
@@ -108,7 +108,7 @@ public function run()
         foreach ($this->playlistFactory->query(null, ['isDynamic' => 1]) as $playlist) {
             try {
                 // We want to detect any differences in what should be assigned to this Playlist.
-                $playlist->load();
+                $playlist->load(['checkDisplayOrder' => true]);
 
                 $this->log->debug('Assessing Playlist: ' . $playlist->name);
 
@@ -128,6 +128,7 @@ public function run()
                 // Query for media which would be assigned to this Playlist and see if there are any differences
                 $media = [];
                 $mediaIds = [];
+                $displayOrder = [];
                 foreach ($this->mediaFactory->query(null, [
                     'name' => $playlist->filterMediaName,
                     'logicalOperatorName' => $playlist->filterMediaNameLogicalOperator,
@@ -137,9 +138,11 @@ public function run()
                     'userCheckUserId' => $playlist->getOwnerId(),
                     'start' => 0,
                     'length' => $playlist->maxNumberOfItems
-                ]) as $item) {
+                ]) as $index => $item) {
                     $media[$item->mediaId] = $item;
                     $mediaIds[] = $item->mediaId;
+                    // store the expected display order
+                    $displayOrder[$item->mediaId] = $index + 1;
                 }
 
                 // Work out if the set of widgets is different or not.
@@ -230,7 +233,8 @@ public function run()
                                 break;
                             }
                             $assignmentMade = true;
-                            $this->createAndAssign($playlist, $item, $count);
+                            // make sure we pass the expected displayOrder for the new item we are about to add.
+                            $this->createAndAssign($playlist, $item, $displayOrder[$item->mediaId]);
                         }
                     }
 
@@ -296,7 +300,8 @@ private function createAndAssign($playlist, $media, $displayOrder)
             $module->widget->calculatedDuration = $mediaDuration;
 
             // Assign the widget to the playlist
-            $playlist->assignWidget($widget);
+            // making sure we pass the displayOrder here, otherwise it would be added to the end of the array.
+            $playlist->assignWidget($widget, $displayOrder);
         }
     }
 }
diff --git a/ui/src/core/file-upload.js b/ui/src/core/file-upload.js
index a576dde45b..e6b43cc9d4 100644
--- a/ui/src/core/file-upload.js
+++ b/ui/src/core/file-upload.js
@@ -44,6 +44,10 @@ function openUploadForm(options) {
         uploadTemplate = Handlebars.compile($("#" + options.templateId).html());
     }
 
+    if (typeof maxImagePixelSize === undefined || maxImagePixelSize === '') {
+        maxImagePixelSize = 0;
+    }
+
     // Handle bars and open a dialog
     var dialog = bootbox.dialog({
         message: uploadTemplate(options.templateOptions),
diff --git a/views/include-file-upload.twig b/views/include-file-upload.twig
index 42bd390323..f004dd73f7 100644
--- a/views/include-file-upload.twig
+++ b/views/include-file-upload.twig
@@ -17,7 +17,7 @@
 
 {# Max image resize size from settings #}
 <script type="text/javascript">
-  const maxImagePixelSize = {{ settings.DEFAULT_RESIZE_LIMIT }};
+  let maxImagePixelSize = "{{ settings.DEFAULT_RESIZE_LIMIT }}";
 </script>
 
 {# Handlebars Templates #}