diff --git a/config/src/test/groovy/org/springframework/security/config/annotation/web/configurers/NamespaceHttpAnonymousTests.groovy b/config/src/test/groovy/org/springframework/security/config/annotation/web/configurers/NamespaceHttpAnonymousTests.groovy
deleted file mode 100644
index 4724169945..0000000000
--- a/config/src/test/groovy/org/springframework/security/config/annotation/web/configurers/NamespaceHttpAnonymousTests.groovy
+++ /dev/null
@@ -1,129 +0,0 @@
-/*
- * Copyright 2002-2013 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
- *
- *      http://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.security.config.annotation.web.configurers;
-
-import org.springframework.context.annotation.Bean;
-import org.springframework.context.annotation.Configuration;
-import org.springframework.security.authentication.AnonymousAuthenticationToken
-import org.springframework.security.config.annotation.BaseSpringSpec;
-import org.springframework.security.config.annotation.web.builders.HttpSecurity;
-import org.springframework.security.config.annotation.web.configuration.BaseWebConfig;
-import org.springframework.security.core.authority.AuthorityUtils;
-import org.springframework.security.web.access.intercept.FilterSecurityInterceptor;
-import org.springframework.security.web.authentication.AnonymousAuthenticationFilter;
-
-/**
- * Tests to verify that all the functionality of <anonymous> attributes is present
- *
- * @author Rob Winch
- *
- */
-public class NamespaceHttpAnonymousTests extends BaseSpringSpec {
-	def "http/anonymous@enabled = true (default)"() {
-		when:
-		loadConfig(AnonymousConfig)
-		then:
-		def filter = findFilter(AnonymousAuthenticationFilter)
-		filter != null
-		def authManager = findFilter(FilterSecurityInterceptor).authenticationManager
-		authManager.authenticate(new AnonymousAuthenticationToken(filter.key, filter.principal, filter.authorities)).authenticated
-	}
-
-	@Configuration
-	static class AnonymousConfig extends BaseWebConfig {
-		@Override
-		protected void configure(HttpSecurity http) {
-			http
-				.authorizeRequests()
-					.anyRequest().hasRole("USER");
-		}
-	}
-
-	def "http/anonymous@enabled = false"() {
-		when:
-		loadConfig(AnonymousDisabledConfig)
-		then:
-		findFilter(AnonymousAuthenticationFilter) == null
-	}
-
-	@Configuration
-	static class AnonymousDisabledConfig extends BaseWebConfig {
-	  protected void configure(HttpSecurity http) {
-				http.anonymous().disable()
-		}
-	}
-
-	def "http/anonymous@granted-authority"() {
-		when:
-		loadConfig(AnonymousGrantedAuthorityConfig)
-		then:
-		findFilter(AnonymousAuthenticationFilter).authorities == AuthorityUtils.createAuthorityList("ROLE_ANON")
-	}
-
-	@Configuration
-	static class AnonymousGrantedAuthorityConfig extends BaseWebConfig {
-		protected void configure(HttpSecurity http) {
-			http
-				.anonymous()
-					.authorities("ROLE_ANON")
-		}
-	}
-
-
-	def "http/anonymous@key"() {
-		when:
-		loadConfig(AnonymousKeyConfig)
-		then:
-		def filter = findFilter(AnonymousAuthenticationFilter)
-		filter != null
-		filter.key == "AnonymousKeyConfig"
-		def authManager = findFilter(FilterSecurityInterceptor).authenticationManager
-		authManager.authenticate(new AnonymousAuthenticationToken(filter.key, filter.principal, filter.authorities)).authenticated
-	}
-
-	@Configuration
-	static class AnonymousKeyConfig extends BaseWebConfig {
-		protected void configure(HttpSecurity http) {
-			http
-				.authorizeRequests()
-					.anyRequest().hasRole("USER")
-					.and()
-				.anonymous().key("AnonymousKeyConfig")
-		}
-	}
-
-	def "http/anonymous@username"() {
-		when:
-		loadConfig(AnonymousUsernameConfig)
-		then:
-		def filter = findFilter(AnonymousAuthenticationFilter)
-		filter != null
-		filter.principal == "AnonymousUsernameConfig"
-		def authManager = findFilter(FilterSecurityInterceptor).authenticationManager
-		authManager.authenticate(new AnonymousAuthenticationToken(filter.key, filter.principal, filter.authorities)).principal == "AnonymousUsernameConfig"
-	}
-
-	@Configuration
-	static class AnonymousUsernameConfig extends BaseWebConfig {
-		protected void configure(HttpSecurity http) {
-			http
-				.authorizeRequests()
-					.anyRequest().hasRole("USER")
-					.and()
-				.anonymous().principal("AnonymousUsernameConfig")
-		}
-	}
-}
diff --git a/config/src/test/java/org/springframework/security/config/annotation/web/configurers/NamespaceHttpAnonymousTests.java b/config/src/test/java/org/springframework/security/config/annotation/web/configurers/NamespaceHttpAnonymousTests.java
new file mode 100644
index 0000000000..6ceff28050
--- /dev/null
+++ b/config/src/test/java/org/springframework/security/config/annotation/web/configurers/NamespaceHttpAnonymousTests.java
@@ -0,0 +1,209 @@
+/*
+ * Copyright 2002-2019 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
+ *
+ *      http://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.security.config.annotation.web.configurers;
+
+import java.util.Optional;
+
+import org.junit.Rule;
+import org.junit.Test;
+
+import org.springframework.beans.factory.annotation.Autowired;
+import org.springframework.security.authentication.AnonymousAuthenticationToken;
+import org.springframework.security.config.annotation.authentication.builders.AuthenticationManagerBuilder;
+import org.springframework.security.config.annotation.web.builders.HttpSecurity;
+import org.springframework.security.config.annotation.web.configuration.EnableWebSecurity;
+import org.springframework.security.config.annotation.web.configuration.WebSecurityConfigurerAdapter;
+import org.springframework.security.config.test.SpringTestRule;
+import org.springframework.security.core.context.SecurityContext;
+import org.springframework.security.core.context.SecurityContextHolder;
+import org.springframework.security.core.userdetails.PasswordEncodedUser;
+import org.springframework.test.web.servlet.MockMvc;
+import org.springframework.web.bind.annotation.GetMapping;
+import org.springframework.web.bind.annotation.RestController;
+
+import static org.springframework.test.web.servlet.request.MockMvcRequestBuilders.get;
+import static org.springframework.test.web.servlet.result.MockMvcResultMatchers.content;
+import static org.springframework.test.web.servlet.result.MockMvcResultMatchers.status;
+
+/**
+ * Tests to verify that all the functionality of <anonymous> attributes is present
+ *
+ * @author Rob Winch
+ * @author Josh Cummings
+ *
+ */
+public class NamespaceHttpAnonymousTests {
+
+	@Autowired
+	MockMvc mvc;
+
+	@Rule
+	public final SpringTestRule spring = new SpringTestRule();
+
+	@Test
+	public void anonymousRequestWhenUsingDefaultAnonymousConfigurationThenUsesAnonymousAuthentication()
+			throws Exception {
+		this.spring.register(AnonymousConfig.class, AnonymousController.class).autowire();
+		this.mvc.perform(get("/type"))
+				.andExpect(content().string(AnonymousAuthenticationToken.class.getSimpleName()));
+	}
+
+	@EnableWebSecurity
+	static class AnonymousConfig extends WebSecurityConfigurerAdapter {
+		@Override
+		protected void configure(HttpSecurity http) throws Exception {
+			// @formatter:off
+			http
+				.authorizeRequests()
+					.antMatchers("/type").anonymous()
+					.anyRequest().denyAll();
+			// @formatter:on
+		}
+	}
+
+	@Test
+	public void anonymousRequestWhenDisablingAnonymousThenDenies()
+			throws Exception {
+		this.spring.register(AnonymousDisabledConfig.class, AnonymousController.class).autowire();
+		this.mvc.perform(get("/type"))
+				.andExpect(status().isForbidden());
+	}
+
+	@EnableWebSecurity
+	static class AnonymousDisabledConfig extends WebSecurityConfigurerAdapter {
+		@Override
+		protected void configure(HttpSecurity http) throws Exception {
+			// @formatter:off
+			http
+				.authorizeRequests()
+					.anyRequest().permitAll()
+					.and()
+				.anonymous().disable();
+			// @formatter:on
+		}
+
+		protected void configure(AuthenticationManagerBuilder auth) throws Exception {
+			// @formatter:off
+			auth
+				.inMemoryAuthentication()
+					.withUser(PasswordEncodedUser.user())
+					.withUser(PasswordEncodedUser.admin());
+			// @formatter:on
+		}
+	}
+
+	@Test
+	public void requestWhenAnonymousThenSendsAnonymousConfiguredAuthorities()
+			throws Exception {
+		this.spring.register(AnonymousGrantedAuthorityConfig.class, AnonymousController.class).autowire();
+		this.mvc.perform(get("/type"))
+				.andExpect(content().string(AnonymousAuthenticationToken.class.getSimpleName()));
+	}
+
+	@EnableWebSecurity
+	static class AnonymousGrantedAuthorityConfig extends WebSecurityConfigurerAdapter {
+		@Override
+		protected void configure(HttpSecurity http) throws Exception {
+			// @formatter:off
+			http
+				.authorizeRequests()
+					.antMatchers("/type").hasRole("ANON")
+					.anyRequest().denyAll()
+					.and()
+				.anonymous()
+					.authorities("ROLE_ANON");
+			// @formatter:on
+		}
+	}
+
+	@Test
+	public void anonymousRequestWhenAnonymousKeyConfiguredThenKeyIsUsed() throws Exception {
+		this.spring.register(AnonymousKeyConfig.class, AnonymousController.class).autowire();
+		this.mvc.perform(get("/key"))
+				.andExpect(content().string(String.valueOf("AnonymousKeyConfig".hashCode())));
+	}
+
+	@EnableWebSecurity
+	static class AnonymousKeyConfig extends WebSecurityConfigurerAdapter {
+		@Override
+		protected void configure(HttpSecurity http) throws Exception {
+			// @formatter:off
+			http
+				.authorizeRequests()
+					.antMatchers("/key").anonymous()
+					.anyRequest().denyAll()
+					.and()
+				.anonymous().key("AnonymousKeyConfig");
+			// @formatter:on
+		}
+	}
+
+	@Test
+	public void anonymousRequestWhenAnonymousUsernameConfiguredThenUsernameIsUsed() throws Exception {
+		this.spring.register(AnonymousUsernameConfig.class, AnonymousController.class).autowire();
+		this.mvc.perform(get("/principal"))
+				.andExpect(content().string("AnonymousUsernameConfig"));
+	}
+
+	@EnableWebSecurity
+	static class AnonymousUsernameConfig extends WebSecurityConfigurerAdapter {
+		@Override
+		protected void configure(HttpSecurity http) throws Exception {
+			// @formatter:off
+			http
+				.authorizeRequests()
+					.antMatchers("/principal").anonymous()
+					.anyRequest().denyAll()
+					.and()
+				.anonymous().principal("AnonymousUsernameConfig");
+			// @formatter:on
+		}
+	}
+
+	@RestController
+	static class AnonymousController {
+		@GetMapping("/type")
+		String type() {
+			return anonymousToken()
+					.map(AnonymousAuthenticationToken::getClass)
+					.map(Class::getSimpleName)
+					.orElse(null);
+		}
+
+		@GetMapping("/key")
+		String key() {
+			return anonymousToken()
+					.map(AnonymousAuthenticationToken::getKeyHash)
+					.map(String::valueOf)
+					.orElse(null);
+		}
+
+		@GetMapping("/principal")
+		String principal() {
+			return anonymousToken()
+					.map(AnonymousAuthenticationToken::getName)
+					.orElse(null);
+		}
+
+		Optional<AnonymousAuthenticationToken> anonymousToken() {
+			return Optional.of(SecurityContextHolder.getContext())
+					.map(SecurityContext::getAuthentication)
+					.filter(a -> a instanceof AnonymousAuthenticationToken)
+					.map(AnonymousAuthenticationToken.class::cast);
+		}
+	}
+
+}