diff --git a/ext/image/main.php b/ext/image/main.php
index c8d51126..c460660c 100644
--- a/ext/image/main.php
+++ b/ext/image/main.php
@@ -224,7 +224,7 @@ class ImageIO extends Extension
 					:hash, :ext, :width, :height, now(), :source
 				)",
             [
-                    "owner_id"=>$user->id, "owner_ip"=>$_SERVER['REMOTE_ADDR'], "filename"=>substr($image->filename, 0, 60), "filesize"=>$image->filesize,
+                "owner_id" => $user->id, "owner_ip" => $_SERVER['REMOTE_ADDR'], "filename" => substr($image->filename, 0, 255), "filesize" => $image->filesize,
                     "hash"=>$image->hash, "ext"=>strtolower($image->ext), "width"=>$image->width, "height"=>$image->height, "source"=>$image->source
                 ]
         );
@@ -342,7 +342,7 @@ class ImageIO extends Extension
 					id = :id
 				",
             [
-                    "filename"=>$image->filename, "filesize"=>$image->filesize, "hash"=>$image->hash,
+                    "filename" => substr($image->filename, 0, 255), "filesize"=>$image->filesize, "hash"=>$image->hash,
                     "ext"=>strtolower($image->ext), "width"=>$image->width, "height"=>$image->height, "source"=>$image->source,
                     "id"=>$id
                 ]
diff --git a/ext/upgrade/main.php b/ext/upgrade/main.php
index 160422b5..5e7d7896 100644
--- a/ext/upgrade/main.php
+++ b/ext/upgrade/main.php
@@ -143,6 +143,25 @@ class Upgrade extends Extension
             log_info("upgrade", "Database at version 15");
             $config->set_bool("in_upgrade", false);
         }
+
+        if ($config->get_int("db_version") < 16) {
+            $config->set_bool("in_upgrade", true);
+            $config->set_int("db_version", 16);
+
+            log_info("upgrade", "Adding tag_id, image_id index to image_tags");
+            $database->execute('CREATE UNIQUE INDEX image_tags_tag_id_image_id_idx ON image_tags(tag_id,image_id) ');
+
+            log_info("upgrade", "Changing filename column to VARCHAR(255)");
+            if ($database->get_driver_name() == DatabaseDriver::PGSQL) {
+                $database->execute('ALTER TABLE images ALTER COLUMN filename SET DATA TYPE VARCHAR(255)');
+            } elseif ($database->get_driver_name() == DatabaseDriver::MYSQL) {
+                $database->execute('ALTER TABLE images MODIFY COLUMN filename VARCHAR(255) NOT NULL');
+            }
+            // SQLite doesn't support altering existing columns? This seems like a problem?
+
+            log_info("upgrade", "Database at version 16");
+            $config->set_bool("in_upgrade", false);
+        }
     }
 
     public function get_priority(): int