diff --git a/Core/src/main/java/com/intellectualcrafters/plot/PS.java b/Core/src/main/java/com/intellectualcrafters/plot/PS.java
index 6e2c33621..da5f70af9 100644
--- a/Core/src/main/java/com/intellectualcrafters/plot/PS.java
+++ b/Core/src/main/java/com/intellectualcrafters/plot/PS.java
@@ -1729,7 +1729,7 @@ public class PS {
                     parent.mkdirs();
                 }
                 MainUtil.sendMessage(sender, "$2 - Output: " + newJar);
-                if (newJar.delete()) {
+                if (!newJar.delete()) {
                     MainUtil.sendMessage(sender, "Failed to update PlotSquared");
                     MainUtil.sendMessage(sender, "Jar file failed to delete.");
                     MainUtil.sendMessage(sender, " - Please update manually");