diff --git a/src/main/java/com/graywolf336/jail/JailMain.java b/src/main/java/com/graywolf336/jail/JailMain.java
index 47bb4f6..2cf39c6 100644
--- a/src/main/java/com/graywolf336/jail/JailMain.java
+++ b/src/main/java/com/graywolf336/jail/JailMain.java
@@ -207,6 +207,11 @@ public class JailMain extends JavaPlugin {
 		return this.sbm;
 	}
 	
+	/** Sets whether the plugin is in debugging or not. */
+	public void setDebugging(boolean debug) {
+		this.debug = debug;
+	}
+	
 	/** Returns if the plugin is in debug state or not. */
 	public boolean inDebug() {
 		return this.debug;
diff --git a/src/main/java/com/graywolf336/jail/legacy/LegacyManager.java b/src/main/java/com/graywolf336/jail/legacy/LegacyManager.java
index 3ad4c44..db45c9e 100644
--- a/src/main/java/com/graywolf336/jail/legacy/LegacyManager.java
+++ b/src/main/java/com/graywolf336/jail/legacy/LegacyManager.java
@@ -80,6 +80,9 @@ public class LegacyManager {
 				case Debug:
 					if(global.contains(s.getString())) {
 						c.set(Settings.DEBUG.getPath(), OldSettings.getGlobalBoolean(global, s));
+						//Only set it true if the old config had true, this way we can still hold the debuggin over
+						//if the old config had it set to false but the new one has it set to true (until a restart/reload)
+						if(c.getBoolean(Settings.DEBUG.getPath())) pl.setDebugging(true);
 						pl.debug(Settings.DEBUG.getPath() + " <-- " + s.getString());
 						count++;
 					}