diff --git a/proxy/src/main/java/net/azisaba/simpleproxy/proxy/ProxyInstance.java b/proxy/src/main/java/net/azisaba/simpleproxy/proxy/ProxyInstance.java
index c8c01ee..ea75cf5 100644
--- a/proxy/src/main/java/net/azisaba/simpleproxy/proxy/ProxyInstance.java
+++ b/proxy/src/main/java/net/azisaba/simpleproxy/proxy/ProxyInstance.java
@@ -37,10 +37,7 @@
 import java.util.Arrays;
 import java.util.List;
 import java.util.Objects;
-import java.util.concurrent.CompletableFuture;
-import java.util.concurrent.ExecutorService;
-import java.util.concurrent.Executors;
-import java.util.concurrent.TimeUnit;
+import java.util.concurrent.*;
 import java.util.concurrent.atomic.AtomicLong;
 
 public class ProxyInstance implements ProxyServer {
@@ -175,7 +172,12 @@ public void handleCommand(@NotNull String input) {
     @Override
     public CompletableFuture<Void> reloadConfig() {
         return CompletableFuture.runAsync(() -> {
-            closeListeners();
+            try {
+                closeListeners();
+            } catch (ExecutionException | InterruptedException | TimeoutException e) {
+                LOGGER.error(e);
+                Thread.currentThread().interrupt();
+            }
             LOGGER.info("Loading config");
             try {
                 ProxyConfigInstance.init();
@@ -238,17 +240,17 @@ public ProxyConfig getConfig() {
         return proxyConfig;
     }
 
-    public void closeListeners() {
+    public void closeListeners() throws ExecutionException, InterruptedException, TimeoutException {
         if (connectionListener != null) {
             LOGGER.info("Closing listeners");
-            connectionListener.closeFutures();
+            connectionListener.closeFutures().get(3, TimeUnit.MINUTES);
         }
     }
 
-    public void fullyCloseListeners() {
+    public void fullyCloseListeners() throws ExecutionException, InterruptedException, TimeoutException {
         if (connectionListener != null) {
             LOGGER.info("Closing listeners");
-            connectionListener.close();
+            connectionListener.close().get(3, TimeUnit.MINUTES);
             connectionListener = null;
         }
     }
@@ -264,13 +266,14 @@ public void stop() {
         } catch (IOException e) {
             LOGGER.warn("Failed to close plugin loader", e);
         }
-        fullyCloseListeners();
-        LOGGER.info("Shutting down executor");
-        worker.shutdownNow();
         try {
+            fullyCloseListeners();
+            LOGGER.info("Shutting down executor");
+            worker.shutdownNow();
             //noinspection ResultOfMethodCallIgnored
             worker.awaitTermination(3, TimeUnit.MINUTES);
-        } catch (InterruptedException e) {
+        } catch (InterruptedException | ExecutionException | TimeoutException e) {
+            LOGGER.error(e);
             Thread.currentThread().interrupt();
         }
         LOGGER.info("Goodbye!");
diff --git a/proxy/src/main/java/net/azisaba/simpleproxy/proxy/connection/ConnectionListener.java b/proxy/src/main/java/net/azisaba/simpleproxy/proxy/connection/ConnectionListener.java
index f719feb..ae830b4 100644
--- a/proxy/src/main/java/net/azisaba/simpleproxy/proxy/connection/ConnectionListener.java
+++ b/proxy/src/main/java/net/azisaba/simpleproxy/proxy/connection/ConnectionListener.java
@@ -31,7 +31,10 @@
 import java.util.ArrayList;
 import java.util.List;
 import java.util.Random;
+import java.util.concurrent.CompletableFuture;
+import java.util.concurrent.ExecutionException;
 import java.util.concurrent.TimeUnit;
+import java.util.concurrent.TimeoutException;
 import java.util.concurrent.atomic.AtomicLong;
 
 public class ConnectionListener {
@@ -193,21 +196,29 @@ protected void initChannel(@NotNull Channel ch) {
                 .connect(serverInfo.getHost(), serverInfo.getPort());
     }
 
-    public void closeFutures() {
-        for (ChannelFuture future : futures) {
-            if (future.channel().isActive() || future.channel().isOpen()) {
-                LOGGER.info("Closing future/listener: {}", future.channel().toString());
-                future.channel().close().syncUninterruptibly();
+    public @NotNull CompletableFuture<Void> closeFutures() {
+        return CompletableFuture.runAsync(() -> {
+            for (ChannelFuture future : futures) {
+                if (future.channel().isActive() || future.channel().isOpen()) {
+                    LOGGER.info("Closing future/listener: {}", future.channel().toString());
+                    future.channel().close().syncUninterruptibly();
+                }
             }
-        }
-        futures.clear();
+            futures.clear();
+        });
     }
 
-    public void close() {
-        closeFutures();
-        LOGGER.info("Shutting down event loop");
-        clientWorkerGroup.shutdownGracefully().syncUninterruptibly();
-        workerGroup.shutdownGracefully().syncUninterruptibly();
-        bossGroup.shutdownGracefully().syncUninterruptibly();
+    public @NotNull CompletableFuture<Void> close() {
+        return CompletableFuture.runAsync(() -> {
+            try {
+                closeFutures().get(3, TimeUnit.MINUTES);
+            } catch (InterruptedException | TimeoutException | ExecutionException e) {
+                LOGGER.error(e);
+            }
+            LOGGER.info("Shutting down event loop");
+            clientWorkerGroup.shutdownGracefully().syncUninterruptibly();
+            workerGroup.shutdownGracefully().syncUninterruptibly();
+            bossGroup.shutdownGracefully().syncUninterruptibly();
+        });
     }
 }