diff --git a/core/imageboard.pack.php b/core/imageboard.pack.php
index a76428b2..517b5a5c 100644
--- a/core/imageboard.pack.php
+++ b/core/imageboard.pack.php
@@ -534,6 +534,11 @@ class Image {
 					continue;
 				}
 
+				if(mb_strlen($tag, 'UTF-8') > 255){
+					flash_message("The tag below is longer than 255 characters, please use a shorter tag.\n$tag\n");
+					continue;
+				}
+
 				$id = $database->get_one(
 						$database->scoreql_to_sql(
 							"SELECT id FROM tags WHERE SCORE_STRNORM(tag) = SCORE_STRNORM(:tag)"
@@ -562,7 +567,7 @@ class Image {
 						array("tag"=>$tag));
 			}
 
-			log_info("core_image", "Tags for Image #{$this->id} set to: ".implode(" ", $tags), false, array("image_id" => $this->id));
+			log_info("core_image", "Tags for Image #{$this->id} set to: ".implode(" ", $tags), null, array("image_id" => $this->id));
 			$database->cache->delete("image-{$this->id}-tags");
 		}
 	}
diff --git a/ext/upgrade/main.php b/ext/upgrade/main.php
index 7322eb33..ce92cd6b 100644
--- a/ext/upgrade/main.php
+++ b/ext/upgrade/main.php
@@ -107,6 +107,26 @@ class Upgrade extends Extension {
 			log_info("upgrade", "Database at version 13");
 			$config->set_bool("in_upgrade", false);
 		}
+
+		if($config->get_int("db_version") < 14) {
+			$config->set_bool("in_upgrade", true);
+			$config->set_int("db_version", 14);
+
+			log_info("upgrade", "Changing tag column to VARCHAR(255)");
+			if($database->get_driver_name() == 'pgsql') {
+				$database->execute('ALTER TABLE tags ALTER COLUMN tag SET DATA TYPE VARCHAR(255)');
+				$database->execute('ALTER TABLE aliases ALTER COLUMN oldtag SET DATA TYPE VARCHAR(255)');
+				$database->execute('ALTER TABLE aliases ALTER COLUMN newtag SET DATA TYPE VARCHAR(255)');
+			}
+			else if($database->get_driver_name() == 'mysql') {
+				$database->execute('ALTER TABLE tags MODIFY COLUMN tag VARCHAR(255) NOT NULL');
+				$database->execute('ALTER TABLE aliases MODIFY COLUMN oldtag VARCHAR(255) NOT NULL');
+				$database->execute('ALTER TABLE aliases MODIFY COLUMN newtag VARCHAR(255) NOT NULL');
+			}
+
+			log_info("upgrade", "Database at version 14");
+			$config->set_bool("in_upgrade", false);
+		}
 	}
 
 	public function get_priority() {return 5;}