diff --git a/api/src/main/java/com/velocitypowered/api/event/player/configuration/PlayerEnterConfigurationEvent.java b/api/src/main/java/com/velocitypowered/api/event/player/configuration/PlayerEnterConfigurationEvent.java
index f0148ef5ac..05d6c2af02 100644
--- a/api/src/main/java/com/velocitypowered/api/event/player/configuration/PlayerEnterConfigurationEvent.java
+++ b/api/src/main/java/com/velocitypowered/api/event/player/configuration/PlayerEnterConfigurationEvent.java
@@ -15,7 +15,9 @@
 /**
  * This event is executed when a player is about to enter the configuration state.
  * It is <b>not</b> called for the initial configuration of a player after login.
- * <p>Velocity will wait for this event before asking the client to enter configuration state.</p>
+ * <p>Velocity will wait for this event before asking the client to enter configuration state.
+ * However due to backend server being unable to keep the connection alive during state changes,
+ * Velocity will only wait for a maximum of 5 seconds.</p>
  *
  * @param player The player who is about to enter configuration state.
  * @param server The server that wants to reconfigure the player.
diff --git a/api/src/main/java/com/velocitypowered/api/event/player/configuration/PlayerFinishConfigurationEvent.java b/api/src/main/java/com/velocitypowered/api/event/player/configuration/PlayerFinishConfigurationEvent.java
index 6b924d445f..50df5a8abe 100644
--- a/api/src/main/java/com/velocitypowered/api/event/player/configuration/PlayerFinishConfigurationEvent.java
+++ b/api/src/main/java/com/velocitypowered/api/event/player/configuration/PlayerFinishConfigurationEvent.java
@@ -15,9 +15,9 @@
 /**
  * This event is executed when a player is about to finish the configuration state.
  * <p>Velocity will wait for this event before asking the client to finish the configuration state.
- * However due to backend server being unable to keep the connection alive for more than 15 seconds,
+ * However due to backend server being unable to keep the connection alive during state changes,
  * Velocity will only wait for a maximum of 5 seconds. If you need to hold a player in configuration
- * state it is recommended to use the {@link PlayerConfigurationEvent}.</p>
+ * state, use the {@link PlayerConfigurationEvent}.</p>
  *
  * @param player The player who is about to finish the configuration phase.
  * @param server The server that has (re-)configured the player.
diff --git a/proxy/src/main/java/com/velocitypowered/proxy/connection/client/ClientConfigSessionHandler.java b/proxy/src/main/java/com/velocitypowered/proxy/connection/client/ClientConfigSessionHandler.java
index 008eaaba5b..7d232b09f8 100644
--- a/proxy/src/main/java/com/velocitypowered/proxy/connection/client/ClientConfigSessionHandler.java
+++ b/proxy/src/main/java/com/velocitypowered/proxy/connection/client/ClientConfigSessionHandler.java
@@ -244,14 +244,14 @@ public CompletableFuture<Void> handleBackendFinishUpdate(VelocityServerConnectio
       smc.write(brandPacket);
     }
 
-    callConfigurationEvent().thenRun(() -> {
-      server.getEventManager().fire(new PlayerFinishConfigurationEvent(player, serverConn))
-          .completeOnTimeout(null, 5, TimeUnit.SECONDS).thenRunAsync(() -> {
-            player.getConnection().write(FinishedUpdatePacket.INSTANCE);
-            player.getConnection().getChannel().pipeline().get(MinecraftEncoder.class).setState(StateRegistry.PLAY);
-            server.getEventManager().fireAndForget(new PlayerFinishedConfigurationEvent(player, serverConn));
-          }, player.getConnection().eventLoop());
-    }).exceptionally(ex -> {
+    callConfigurationEvent().thenCompose(v -> {
+      return server.getEventManager().fire(new PlayerFinishConfigurationEvent(player, serverConn))
+          .completeOnTimeout(null, 5, TimeUnit.SECONDS);
+    }).thenRunAsync(() -> {
+      player.getConnection().write(FinishedUpdatePacket.INSTANCE);
+      player.getConnection().getChannel().pipeline().get(MinecraftEncoder.class).setState(StateRegistry.PLAY);
+      server.getEventManager().fireAndForget(new PlayerFinishedConfigurationEvent(player, serverConn));
+    }, player.getConnection().eventLoop()).exceptionally(ex -> {
       logger.error("Error finishing configuration state:", ex);
       return null;
     });
diff --git a/proxy/src/main/java/com/velocitypowered/proxy/connection/client/ConnectedPlayer.java b/proxy/src/main/java/com/velocitypowered/proxy/connection/client/ConnectedPlayer.java
index b855b54c93..11f6b52982 100644
--- a/proxy/src/main/java/com/velocitypowered/proxy/connection/client/ConnectedPlayer.java
+++ b/proxy/src/main/java/com/velocitypowered/proxy/connection/client/ConnectedPlayer.java
@@ -1274,15 +1274,16 @@ private boolean sendKeepAliveToBackend(final @Nullable VelocityServerConnection
    * Switches the connection to the client into config state.
    */
   public void switchToConfigState() {
-    server.getEventManager().fire(new PlayerEnterConfigurationEvent(this, getConnectionInFlightOrConnectedServer())).thenRunAsync(() -> {
-      connection.write(StartUpdatePacket.INSTANCE);
-      connection.getChannel().pipeline().get(MinecraftEncoder.class).setState(StateRegistry.CONFIG);
-      // Make sure we don't send any play packets to the player after update start
-      connection.addPlayPacketQueueHandler();
-    }, connection.eventLoop()).exceptionally((ex) -> {
-      logger.error("Error switching player connection to config state", ex);
-      return null;
-    });
+    server.getEventManager().fire(new PlayerEnterConfigurationEvent(this, getConnectionInFlightOrConnectedServer()))
+        .completeOnTimeout(null, 5, TimeUnit.SECONDS).thenRunAsync(() -> {
+          connection.write(StartUpdatePacket.INSTANCE);
+          connection.getChannel().pipeline().get(MinecraftEncoder.class).setState(StateRegistry.CONFIG);
+          // Make sure we don't send any play packets to the player after update start
+          connection.addPlayPacketQueueHandler();
+        }, connection.eventLoop()).exceptionally((ex) -> {
+          logger.error("Error switching player connection to config state", ex);
+          return null;
+        });
   }
 
   /**