diff --git a/Plan/src/main/java/com/djrapitops/plan/system/settings/config/ConfigSystem.java b/Plan/src/main/java/com/djrapitops/plan/system/settings/config/ConfigSystem.java
index 2eacbf7e2..ed3188ee4 100644
--- a/Plan/src/main/java/com/djrapitops/plan/system/settings/config/ConfigSystem.java
+++ b/Plan/src/main/java/com/djrapitops/plan/system/settings/config/ConfigSystem.java
@@ -9,12 +9,16 @@ import com.djrapitops.plan.system.SubSystem;
 import com.djrapitops.plan.system.file.PlanFiles;
 import com.djrapitops.plan.system.settings.Settings;
 import com.djrapitops.plan.system.settings.theme.Theme;
-import com.djrapitops.plugin.api.utility.log.Log;
 import com.djrapitops.plugin.logging.L;
+import com.djrapitops.plugin.logging.console.PluginLogger;
+import com.djrapitops.plugin.logging.debug.*;
 import com.djrapitops.plugin.logging.error.ErrorHandler;
+import com.djrapitops.plugin.utilities.Verify;
 
 import javax.inject.Singleton;
 import java.io.IOException;
+import java.util.ArrayList;
+import java.util.List;
 
 /**
  * System for Config and other user customizable options.
@@ -27,17 +31,20 @@ public abstract class ConfigSystem implements SubSystem {
     protected final PlanFiles files;
     protected final PlanConfig config;
     protected final Theme theme;
+    private final PluginLogger logger;
     protected final ErrorHandler errorHandler;
 
     public ConfigSystem(
             PlanFiles files,
             PlanConfig config,
             Theme theme,
+            PluginLogger logger,
             ErrorHandler errorHandler
     ) {
         this.files = files;
         this.config = config;
         this.theme = theme;
+        this.logger = logger;
         this.errorHandler = errorHandler;
     }
 
@@ -55,14 +62,30 @@ public abstract class ConfigSystem implements SubSystem {
             copyDefaults();
             config.save();
 
-            // TODO Set Debug logger somewhere
-            Log.setDebugMode(config.getString(Settings.DEBUG));
+            setDebugMode();
         } catch (IOException e) {
             throw new EnableException("Failed to save default config.", e);
         }
         theme.enable();
     }
 
+    private void setDebugMode() {
+        String debugMode = config.getString(Settings.DEBUG);
+
+        List<DebugLogger> loggers = new ArrayList<>();
+        if (Verify.equalsOne(debugMode, "true", "both", "console")) {
+            loggers.add(new ConsoleDebugLogger(logger));
+        }
+        if (Verify.equalsOne(debugMode, "true", "both", "file")) {
+            loggers.add(new FolderTimeStampFileDebugLogger(files.getLogsFolder(), () -> errorHandler));
+        }
+        if (logger.getDebugLogger() instanceof CombineDebugLogger) {
+            CombineDebugLogger debugLogger = (CombineDebugLogger) logger.getDebugLogger();
+            loggers.add(debugLogger.getDebugLogger(MemoryDebugLogger.class).orElse(new MemoryDebugLogger()));
+            debugLogger.setDebugLoggers(loggers.toArray(new DebugLogger[0]));
+        }
+    }
+
     /**
      * Copies default values from file in jar to Config.
      *