diff --git a/Plan/src/main/java/com/djrapitops/plan/system/processing/Processing.java b/Plan/src/main/java/com/djrapitops/plan/system/processing/Processing.java
index 35a039693..ce9e9df9a 100644
--- a/Plan/src/main/java/com/djrapitops/plan/system/processing/Processing.java
+++ b/Plan/src/main/java/com/djrapitops/plan/system/processing/Processing.java
@@ -9,6 +9,7 @@ import com.djrapitops.plan.system.locale.lang.PluginLang;
 import com.djrapitops.plugin.StaticHolder;
 import com.djrapitops.plugin.api.utility.log.Log;
 import com.djrapitops.plugin.utilities.Verify;
+import com.google.common.util.concurrent.ThreadFactoryBuilder;
 
 import java.util.List;
 import java.util.concurrent.*;
@@ -23,8 +24,8 @@ public class Processing implements SubSystem {
 
     public Processing(Supplier<Locale> locale) {
         this.locale = locale;
-        nonCriticalExecutor = Executors.newFixedThreadPool(6);
-        criticalExecutor = Executors.newFixedThreadPool(2);
+        nonCriticalExecutor = Executors.newFixedThreadPool(6, new ThreadFactoryBuilder().setNameFormat("Plan Non critical-pool-%d").build());
+        criticalExecutor = Executors.newFixedThreadPool(2, new ThreadFactoryBuilder().setNameFormat("Plan Critical-pool-%d").build());
         saveInstance(nonCriticalExecutor);
         saveInstance(criticalExecutor);
         saveInstance(this);
diff --git a/Plan/src/main/java/com/djrapitops/plan/system/webserver/WebServer.java b/Plan/src/main/java/com/djrapitops/plan/system/webserver/WebServer.java
index c8d90b4e3..d2b4a4a87 100644
--- a/Plan/src/main/java/com/djrapitops/plan/system/webserver/WebServer.java
+++ b/Plan/src/main/java/com/djrapitops/plan/system/webserver/WebServer.java
@@ -12,6 +12,7 @@ import com.djrapitops.plugin.StaticHolder;
 import com.djrapitops.plugin.api.Check;
 import com.djrapitops.plugin.api.utility.log.Log;
 import com.djrapitops.plugin.utilities.Verify;
+import com.google.common.util.concurrent.ThreadFactoryBuilder;
 import com.sun.net.httpserver.HttpServer;
 import com.sun.net.httpserver.HttpsConfigurator;
 import com.sun.net.httpserver.HttpsParameters;
@@ -27,9 +28,7 @@ import java.nio.file.Paths;
 import java.security.*;
 import java.security.cert.Certificate;
 import java.security.cert.CertificateException;
-import java.util.concurrent.ArrayBlockingQueue;
-import java.util.concurrent.ThreadPoolExecutor;
-import java.util.concurrent.TimeUnit;
+import java.util.concurrent.*;
 import java.util.function.Supplier;
 
 /**
@@ -108,7 +107,11 @@ public class WebServer implements SubSystem {
             }
             server.createContext("/", requestHandler);
 
-            server.setExecutor(new ThreadPoolExecutor(4, 8, 30, TimeUnit.SECONDS, new ArrayBlockingQueue<>(100)));
+            ExecutorService executor = new ThreadPoolExecutor(
+                    4, 8, 30, TimeUnit.SECONDS, new ArrayBlockingQueue<>(100),
+                    new ThreadFactoryBuilder().setNameFormat("Plan WebServer Thread-%d").build()
+            );
+            server.setExecutor(executor);
             server.start();
 
             enabled = true;
@@ -199,12 +202,26 @@ public class WebServer implements SubSystem {
     @Override
     public void disable() {
         if (server != null) {
+            shutdown();
             Log.info(locale.get().getString(PluginLang.DISABLED_WEB_SERVER));
-            server.stop(0);
         }
         enabled = false;
     }
 
+    private void shutdown() {
+        server.stop(0);
+        Executor executor = server.getExecutor();
+        if (executor instanceof ExecutorService) {
+            ExecutorService service = (ExecutorService) executor;
+            service.shutdown();
+            try {
+                service.awaitTermination(5, TimeUnit.SECONDS);
+            } catch (InterruptedException timeoutExceededEx) {
+                service.shutdownNow();
+            }
+        }
+    }
+
     public String getProtocol() {
         return usingHttps ? "https" : "http";
     }