diff --git a/Plan/bukkit/src/test/java/com/djrapitops/plan/BukkitSystemTest.java b/Plan/bukkit/src/test/java/com/djrapitops/plan/BukkitSystemTest.java
index f76eba214..65f0fabcc 100644
--- a/Plan/bukkit/src/test/java/com/djrapitops/plan/BukkitSystemTest.java
+++ b/Plan/bukkit/src/test/java/com/djrapitops/plan/BukkitSystemTest.java
@@ -17,7 +17,10 @@
 package com.djrapitops.plan;
 
 import com.djrapitops.plan.api.exceptions.EnableException;
+import com.djrapitops.plan.db.Database;
+import com.djrapitops.plan.db.access.queries.objects.ServerQueries;
 import com.djrapitops.plan.system.PlanSystem;
+import com.djrapitops.plan.system.info.server.Server;
 import com.djrapitops.plan.system.settings.ConfigSettingKeyTest;
 import com.djrapitops.plan.system.settings.config.PlanConfig;
 import com.djrapitops.plan.system.settings.paths.WebserverSettings;
@@ -31,9 +34,11 @@ import org.junit.runner.RunWith;
 import org.mockito.junit.MockitoJUnitRunner;
 import rules.BukkitComponentMocker;
 import rules.ComponentMocker;
+import utilities.OptionalAssert;
 import utilities.RandomData;
 
 import java.util.Collection;
+import java.util.Optional;
 
 import static org.junit.Assert.assertTrue;
 
@@ -71,6 +76,21 @@ public class BukkitSystemTest {
         }
     }
 
+    @Test
+    public void correctWebAddressInDatabaseAfterEnable() throws EnableException {
+        try {
+            system.enable();
+            Database database = system.getDatabaseSystem().getDatabase();
+            String expectedAddress = system.getWebServerSystem().getWebServer().getAccessAddress();
+            Optional<String> found = database.query(ServerQueries.fetchServerMatchingIdentifier(system.getServerInfo().getServerUUID()))
+                    .map(Server::getWebAddress);
+
+            OptionalAssert.equals(expectedAddress, found);
+        } finally {
+            system.disable();
+        }
+    }
+
     @Test
     public void bukkitSystemHasDefaultConfigValuesAfterEnable() throws EnableException, IllegalAccessException {
         try {
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/system/PlanSystem.java b/Plan/common/src/main/java/com/djrapitops/plan/system/PlanSystem.java
index 3c459df91..a1610fc04 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/system/PlanSystem.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/system/PlanSystem.java
@@ -126,9 +126,9 @@ public class PlanSystem implements SubSystem {
                 localeSystem,
                 versionCheckSystem,
                 databaseSystem,
+                webServerSystem,
                 processing,
                 serverInfo,
-                webServerSystem,
                 importSystem,
                 exportSystem,
                 infoSystem,
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/system/webserver/WebServer.java b/Plan/common/src/main/java/com/djrapitops/plan/system/webserver/WebServer.java
index 164089a0b..caa057e60 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/system/webserver/WebServer.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/system/webserver/WebServer.java
@@ -25,6 +25,7 @@ import com.djrapitops.plan.system.locale.Locale;
 import com.djrapitops.plan.system.locale.lang.PluginLang;
 import com.djrapitops.plan.system.settings.config.PlanConfig;
 import com.djrapitops.plan.system.settings.paths.WebserverSettings;
+import com.djrapitops.plugin.api.Check;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
 import com.djrapitops.plugin.logging.error.ErrorHandler;
@@ -101,7 +102,7 @@ public class WebServer implements SubSystem {
         initServer();
 
         if (!isEnabled()) {
-            if (serverInfo.getServer().isProxy()) {
+            if (Check.isBungeeAvailable() || Check.isVelocityAvailable()) {
                 throw new EnableException(locale.getString(PluginLang.ENABLE_FAIL_NO_WEB_SERVER_PROXY));
             }
             if (config.isTrue(WebserverSettings.DISABLED)) {
@@ -118,8 +119,8 @@ public class WebServer implements SubSystem {
      * Starts up the WebServer in a new Thread Pool.
      */
     private void initServer() {
-        if (serverInfo.getServer().isNotProxy() && config.isTrue(WebserverSettings.DISABLED)) {
-            // Bukkit WebServer has been disabled.
+        if ((Check.isBukkitAvailable() || Check.isSpongeAvailable()) && config.isTrue(WebserverSettings.DISABLED)) {
+            // Bukkit/Sponge WebServer has been disabled.
             return;
         }