diff --git a/spring-boot-system-tests/spring-boot-deployment-tests/build.gradle b/spring-boot-system-tests/spring-boot-deployment-tests/build.gradle
index 1038367578f9..52b5518903e1 100644
--- a/spring-boot-system-tests/spring-boot-deployment-tests/build.gradle
+++ b/spring-boot-system-tests/spring-boot-deployment-tests/build.gradle
@@ -17,10 +17,11 @@ configurations.all {
 }
 
 dependencies {
+	implementation(project(":spring-boot-project:spring-boot-starters:spring-boot-starter-actuator"))
+	implementation(project(":spring-boot-project:spring-boot-starters:spring-boot-starter-security"))
 	implementation(project(":spring-boot-project:spring-boot-starters:spring-boot-starter-web")) {
 		exclude group: "org.hibernate.validator"
 	}
-	implementation(project(":spring-boot-project:spring-boot-starters:spring-boot-starter-actuator"))
 
 	systemTestImplementation(enforcedPlatform(project(path: ":spring-boot-project:spring-boot-parent")))
 	systemTestImplementation(project(":spring-boot-project:spring-boot-starters:spring-boot-starter-test"))
diff --git a/spring-boot-system-tests/spring-boot-deployment-tests/src/main/resources/application.yml b/spring-boot-system-tests/spring-boot-deployment-tests/src/main/resources/application.yml
index 8099f86ce86d..9b5ee87fe1bb 100644
--- a/spring-boot-system-tests/spring-boot-deployment-tests/src/main/resources/application.yml
+++ b/spring-boot-system-tests/spring-boot-deployment-tests/src/main/resources/application.yml
@@ -1 +1,6 @@
+spring:
+  security:
+    user:
+      name: test
+      password: test
 management.endpoints.web.exposure.include: '*'
diff --git a/spring-boot-system-tests/spring-boot-deployment-tests/src/systemTest/java/org/springframework/boot/deployment/AbstractDeploymentTests.java b/spring-boot-system-tests/spring-boot-deployment-tests/src/systemTest/java/org/springframework/boot/deployment/AbstractDeploymentTests.java
index fa79709ba57a..6ca992192be3 100644
--- a/spring-boot-system-tests/spring-boot-deployment-tests/src/systemTest/java/org/springframework/boot/deployment/AbstractDeploymentTests.java
+++ b/spring-boot-system-tests/spring-boot-deployment-tests/src/systemTest/java/org/springframework/boot/deployment/AbstractDeploymentTests.java
@@ -95,6 +95,7 @@ private void test(Consumer<TestRestTemplate> consumer) {
 			TestRestTemplate rest = new TestRestTemplate(new RestTemplateBuilder()
 					.rootUri("http://" + this.container.getHost() + ":" + this.container.getMappedPort(this.port)
 							+ "/spring-boot")
+					.basicAuthentication("test", "test")
 					.requestFactory(() -> new HttpComponentsClientHttpRequestFactory(HttpClients.custom()
 							.setRetryHandler(new StandardHttpRequestRetryHandler(10, false)).build())));
 			try {
diff --git a/spring-boot-system-tests/spring-boot-deployment-tests/src/systemTest/java/org/springframework/boot/deployment/Tomcat85DeploymentTests.java b/spring-boot-system-tests/spring-boot-deployment-tests/src/systemTest/java/org/springframework/boot/deployment/Tomcat85DeploymentTests.java
new file mode 100644
index 000000000000..88ce8a6d898b
--- /dev/null
+++ b/spring-boot-system-tests/spring-boot-deployment-tests/src/systemTest/java/org/springframework/boot/deployment/Tomcat85DeploymentTests.java
@@ -0,0 +1,39 @@
+/*
+ * Copyright 2012-2021 the original author or authors.
+ *
+ * Licensed 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 org.springframework.boot.deployment;
+
+import org.testcontainers.junit.jupiter.Container;
+import org.testcontainers.junit.jupiter.Testcontainers;
+
+/**
+ * Deployment tests for Tomcat 8.5 (a Servlet 3.1 container).
+ *
+ * @author Andy Wilkinson
+ */
+@Testcontainers(disabledWithoutDocker = true)
+class Tomcat85DeploymentTests extends AbstractDeploymentTests {
+
+	@Container
+	static WarDeploymentContainer container = new WarDeploymentContainer("tomcat:8.5.73-jdk8-openjdk",
+			"/usr/local/tomcat/webapps", DEFAULT_PORT);
+
+	@Override
+	WarDeploymentContainer getContainer() {
+		return container;
+	}
+
+}