diff --git a/connect/runtime/src/main/java/org/apache/kafka/connect/runtime/rest/RestServer.java b/connect/runtime/src/main/java/org/apache/kafka/connect/runtime/rest/RestServer.java
index 8cd3583fbd7c3..6013830160053 100644
--- a/connect/runtime/src/main/java/org/apache/kafka/connect/runtime/rest/RestServer.java
+++ b/connect/runtime/src/main/java/org/apache/kafka/connect/runtime/rest/RestServer.java
@@ -348,6 +348,13 @@ public void stop() {
         log.info("Stopping REST server");
 
         try {
+            if (handlers.isRunning()) {
+                for (Handler handler : handlers.getHandlers()) {
+                    if (handler != null) {
+                        Utils.closeQuietly(handler::stop, handler.toString());
+                    }
+                }
+            }
             for (ConnectRestExtension connectRestExtension : connectRestExtensions) {
                 try {
                     connectRestExtension.close();
@@ -358,8 +365,13 @@ public void stop() {
             jettyServer.stop();
             jettyServer.join();
         } catch (Exception e) {
-            jettyServer.destroy();
             throw new ConnectException("Unable to stop REST server", e);
+        } finally {
+            try {
+                jettyServer.destroy();
+            } catch (Exception e) {
+                log.error("Unable to destroy REST server", e);
+            }
         }
 
         log.info("REST server stopped");