diff --git a/core/src/main/java/com/linecorp/armeria/server/docs/DocService.java b/core/src/main/java/com/linecorp/armeria/server/docs/DocService.java
index a6d2ee14955..7101cfe7401 100644
--- a/core/src/main/java/com/linecorp/armeria/server/docs/DocService.java
+++ b/core/src/main/java/com/linecorp/armeria/server/docs/DocService.java
@@ -64,7 +64,6 @@
 import com.linecorp.armeria.server.HttpService;
 import com.linecorp.armeria.server.Server;
 import com.linecorp.armeria.server.ServerConfig;
-import com.linecorp.armeria.server.ServerListenerAdapter;
 import com.linecorp.armeria.server.Service;
 import com.linecorp.armeria.server.ServiceConfig;
 import com.linecorp.armeria.server.ServiceRequestContext;
@@ -189,23 +188,18 @@ public void serviceAdded(ServiceConfig cfg) throws Exception {
         server = cfg.server();
 
         // Build the Specification after all the services are added to the server.
-        server.addListener(new ServerListenerAdapter() {
-            @Override
-            public void serverStarting(Server server) throws Exception {
-                final ServerConfig config = server.config();
-                final List<VirtualHost> virtualHosts = config.findVirtualHosts(DocService.this);
-
-                final List<ServiceConfig> services =
-                        config.serviceConfigs().stream()
-                              .filter(se -> virtualHosts.contains(se.virtualHost()))
-                              .collect(toImmutableList());
-                final ExecutorService executorService = Executors.newSingleThreadExecutor(
-                        ThreadFactories.newThreadFactory("docservice-loader", true));
-                vfs().specificationLoader.updateServices(services, executorService).handle((res, e) -> {
-                    executorService.shutdown();
-                    return null;
-                });
-            }
+        final ServerConfig config = server.config();
+        final List<VirtualHost> virtualHosts = config.findVirtualHosts(this);
+
+        final List<ServiceConfig> services =
+                config.serviceConfigs().stream()
+                      .filter(se -> virtualHosts.contains(se.virtualHost()))
+                      .collect(toImmutableList());
+        final ExecutorService executorService = Executors.newSingleThreadExecutor(
+                ThreadFactories.newThreadFactory("docservice-loader", true));
+        vfs().specificationLoader.updateServices(services, executorService).handle((res, e) -> {
+            executorService.shutdown();
+            return null;
         });
     }
 
diff --git a/core/src/test/java/com/linecorp/armeria/server/docs/DocServiceReconfigureTest.java b/core/src/test/java/com/linecorp/armeria/server/docs/DocServiceReconfigureTest.java
new file mode 100644
index 00000000000..ac67a49091a
--- /dev/null
+++ b/core/src/test/java/com/linecorp/armeria/server/docs/DocServiceReconfigureTest.java
@@ -0,0 +1,64 @@
+/*
+ * Copyright 2022 LINE Corporation
+ *
+ * LINE Corporation licenses this file to you under the Apache License,
+ * version 2.0 (the "License"); you may not use this file except in compliance
+ * with the License. You may obtain a copy of the License at:
+ *
+ *   https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS, WITHOUT
+ * WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied. See the
+ * License for the specific language governing permissions and limitations
+ * under the License.
+ */
+
+package com.linecorp.armeria.server.docs;
+
+import static net.javacrumbs.jsonunit.fluent.JsonFluentAssert.assertThatJson;
+
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.RegisterExtension;
+
+import com.linecorp.armeria.server.ServerBuilder;
+import com.linecorp.armeria.server.annotation.Get;
+import com.linecorp.armeria.testing.junit5.server.ServerExtension;
+
+class DocServiceReconfigureTest {
+
+    @RegisterExtension
+    static ServerExtension server = new ServerExtension() {
+        @Override
+        protected void configure(ServerBuilder sb) throws Exception {
+            sb.annotatedService("/service", new Object() {
+                @Get("/before")
+                public void before() {
+                }
+            });
+            sb.serviceUnder("/docs", DocService.builder().build());
+        }
+    };
+
+    @Test
+    void testReconfigure() {
+        String specification = server.blockingWebClient().get("/docs/specification.json").contentUtf8();
+        assertThatJson(specification).node("services").isArray().ofLength(1);
+        assertThatJson(specification).node("services[0].methods").isArray().ofLength(1);
+        assertThatJson(specification).node("services[0].methods[0].name").isEqualTo("before");
+
+        server.server().reconfigure(sb -> {
+            sb.annotatedService("/service", new Object() {
+                @Get("/after")
+                public void after() {
+                }
+            });
+            sb.serviceUnder("/docs", DocService.builder().build());
+        });
+
+        specification = server.blockingWebClient().get("/docs/specification.json").contentUtf8();
+        assertThatJson(specification).node("services").isArray().ofLength(1);
+        assertThatJson(specification).node("services[0].methods").isArray().ofLength(1);
+        assertThatJson(specification).node("services[0].methods[0].name").isEqualTo("after");
+    }
+}