diff --git a/config/src/main/java/org/springframework/security/config/annotation/web/AbstractRequestMatcherRegistry.java b/config/src/main/java/org/springframework/security/config/annotation/web/AbstractRequestMatcherRegistry.java
index 504f3b98408..29d3e1b848f 100644
--- a/config/src/main/java/org/springframework/security/config/annotation/web/AbstractRequestMatcherRegistry.java
+++ b/config/src/main/java/org/springframework/security/config/annotation/web/AbstractRequestMatcherRegistry.java
@@ -427,12 +427,20 @@ RequestMatcher requestMatcher(ServletContext servletContext) {
 
 		@Override
 		public boolean matches(HttpServletRequest request) {
-			return this.requestMatcherFactory.apply(request.getServletContext()).matches(request);
+			ServletContext servletContext = request.getServletContext();
+			if (servletContext == null) {
+				return false;
+			}
+			return this.requestMatcherFactory.apply(servletContext).matches(request);
 		}
 
 		@Override
 		public MatchResult matcher(HttpServletRequest request) {
-			return this.requestMatcherFactory.apply(request.getServletContext()).matcher(request);
+			ServletContext servletContext = request.getServletContext();
+			if (servletContext == null) {
+				return MatchResult.notMatch();
+			}
+			return this.requestMatcherFactory.apply(servletContext).matcher(request);
 		}
 
 		@Override
diff --git a/config/src/test/java/org/springframework/security/config/annotation/web/AbstractRequestMatcherRegistryTests.java b/config/src/test/java/org/springframework/security/config/annotation/web/AbstractRequestMatcherRegistryTests.java
index 3d5b25c7661..e829f4c453a 100644
--- a/config/src/test/java/org/springframework/security/config/annotation/web/AbstractRequestMatcherRegistryTests.java
+++ b/config/src/test/java/org/springframework/security/config/annotation/web/AbstractRequestMatcherRegistryTests.java
@@ -42,6 +42,7 @@
 import org.springframework.security.web.util.matcher.DispatcherTypeRequestMatcher;
 import org.springframework.security.web.util.matcher.RegexRequestMatcher;
 import org.springframework.security.web.util.matcher.RequestMatcher;
+import org.springframework.test.util.ReflectionTestUtils;
 import org.springframework.test.web.servlet.MockMvc;
 import org.springframework.test.web.servlet.setup.MockMvcBuilders;
 import org.springframework.web.context.WebApplicationContext;
@@ -358,6 +359,19 @@ public void matchesWhenNoMappingThenException() {
 		assertThatExceptionOfType(IllegalArgumentException.class).isThrownBy(() -> requestMatcher.matcher(request));
 	}
 
+	@Test
+	public void requestMatchersWhenServletContextCanBeNullThenDisallow() {
+		TestDeferredRequestMatcherRegistry deferredRequestMatcherRegistry = new TestDeferredRequestMatcherRegistry();
+		deferredRequestMatcherRegistry.setApplicationContext(this.context);
+		List<RequestMatcher> requestMatchers = deferredRequestMatcherRegistry.requestMatchers("/**");
+		MockHttpServletRequest request = new MockHttpServletRequest(HttpMethod.GET.name(), "/endpoint");
+
+		ReflectionTestUtils.setField(request, "servletContext", null);
+
+		assertThat(requestMatchers).isNotEmpty().hasSize(1);
+		assertThat(requestMatchers.get(0).matches(request)).isFalse();
+	}
+
 	private void mockMvcIntrospector(boolean isPresent) {
 		ApplicationContext context = this.matcherRegistry.getApplicationContext();
 		given(context.containsBean("mvcHandlerMappingIntrospector")).willReturn(isPresent);
@@ -392,6 +406,16 @@ private List<RequestMatcher> unwrap(List<RequestMatcher> wrappedMatchers) {
 
 	}
 
+	private static class TestDeferredRequestMatcherRegistry
+			extends AbstractRequestMatcherRegistry<List<RequestMatcher>> {
+
+		@Override
+		protected List<RequestMatcher> chainRequestMatchers(List<RequestMatcher> requestMatchers) {
+			return requestMatchers;
+		}
+
+	}
+
 	@Configuration
 	@EnableWebSecurity
 	@EnableWebMvc
diff --git a/web/src/main/java/org/springframework/security/web/FilterInvocation.java b/web/src/main/java/org/springframework/security/web/FilterInvocation.java
index 26874c31be5..cb99c74d865 100644
--- a/web/src/main/java/org/springframework/security/web/FilterInvocation.java
+++ b/web/src/main/java/org/springframework/security/web/FilterInvocation.java
@@ -26,6 +26,7 @@
 import java.util.Collections;
 import java.util.Enumeration;
 import java.util.LinkedHashMap;
+import java.util.LinkedHashSet;
 import java.util.List;
 import java.util.Map;
 
@@ -178,6 +179,8 @@ static class DummyRequest extends HttpServletRequestWrapper {
 
 		private final Map<String, String[]> parameters = new LinkedHashMap<>();
 
+		private final Map<String, Object> attributes = new LinkedHashMap<>();
+
 		DummyRequest() {
 			super(UNSUPPORTED_REQUEST);
 		}
@@ -189,7 +192,7 @@ public String getCharacterEncoding() {
 
 		@Override
 		public Object getAttribute(String attributeName) {
-			return null;
+			return this.attributes.get(attributeName);
 		}
 
 		void setRequestURI(String requestURI) {
@@ -317,6 +320,23 @@ void setServletContext(ServletContext servletContext) {
 			this.servletContext = servletContext;
 		}
 
+		@Override
+		public void setAttribute(String name, Object value) {
+			Assert.notNull(name, "name can not be null");
+			this.attributes.put(name, value);
+		}
+
+		@Override
+		public void removeAttribute(String name) {
+			Assert.notNull(name, "name can not be null");
+			this.attributes.remove(name);
+		}
+
+		@Override
+		public Enumeration<String> getAttributeNames() {
+			return Collections.enumeration(new LinkedHashSet<>(this.attributes.keySet()));
+		}
+
 	}
 
 	static final class UnsupportedOperationExceptionInvocationHandler implements InvocationHandler {
diff --git a/web/src/test/java/org/springframework/security/web/FilterInvocationTests.java b/web/src/test/java/org/springframework/security/web/FilterInvocationTests.java
index 98dafa27fc3..6f5715c850b 100644
--- a/web/src/test/java/org/springframework/security/web/FilterInvocationTests.java
+++ b/web/src/test/java/org/springframework/security/web/FilterInvocationTests.java
@@ -163,4 +163,15 @@ public void testDummyRequestGetHeadersNull() {
 		assertThatExceptionOfType(NoSuchElementException.class).isThrownBy(headers::nextElement);
 	}
 
+	@Test
+	public void testDummyRequestGetAttribute() {
+		DummyRequest request = new DummyRequest();
+		request.setAttribute("name", "value");
+		request.setAttribute("removeName", "removeValue");
+		request.removeAttribute("removeName");
+		Enumeration<String> attributeNames = request.getAttributeNames();
+		assertThat(attributeNames.nextElement()).isEqualTo("name");
+		assertThatExceptionOfType(NoSuchElementException.class).isThrownBy(attributeNames::nextElement);
+	}
+
 }