Instrument Filter Chain

Closes gh-11911

config/src/main/java/org/springframework/security/config/annotation/web/builders/WebSecurity.java

@@ -19,6 +19,7 @@ package org.springframework.security.config.annotation.web.builders;
 import java.util.ArrayList;
 import java.util.List;
 
+import io.micrometer.observation.ObservationRegistry;
 import jakarta.servlet.Filter;
 import jakarta.servlet.ServletContext;
 import jakarta.servlet.http.HttpServletRequest;
@@ -45,6 +46,7 @@ import org.springframework.security.core.context.SecurityContext;
 import org.springframework.security.web.DefaultSecurityFilterChain;
 import org.springframework.security.web.FilterChainProxy;
 import org.springframework.security.web.FilterInvocation;
+import org.springframework.security.web.ObservationFilterChainDecorator;
 import org.springframework.security.web.SecurityFilterChain;
 import org.springframework.security.web.access.AuthorizationManagerWebInvocationPrivilegeEvaluator;
 import org.springframework.security.web.access.DefaultWebInvocationPrivilegeEvaluator;
@@ -101,6 +103,8 @@ public final class WebSecurity extends AbstractConfiguredSecurityBuilder<Filter,
 
 	private WebInvocationPrivilegeEvaluator privilegeEvaluator;
 
+	private ObservationRegistry observationRegistry = ObservationRegistry.NOOP;
+
 	private DefaultWebSecurityExpressionHandler defaultWebSecurityExpressionHandler = new DefaultWebSecurityExpressionHandler();
 
 	private SecurityExpressionHandler<FilterInvocation> expressionHandler = this.defaultWebSecurityExpressionHandler;
@@ -303,6 +307,7 @@ public final class WebSecurity extends AbstractConfiguredSecurityBuilder<Filter,
 		if (this.requestRejectedHandler != null) {
 			filterChainProxy.setRequestRejectedHandler(this.requestRejectedHandler);
 		}
+		filterChainProxy.setFilterChainDecorator(getFilterChainDecorator());
 		filterChainProxy.afterPropertiesSet();
 
 		Filter result = filterChainProxy;
@@ -366,6 +371,11 @@ public final class WebSecurity extends AbstractConfiguredSecurityBuilder<Filter,
 		}
 		catch (NoSuchBeanDefinitionException ex) {
 		}
+		try {
+			this.observationRegistry = applicationContext.getBean(ObservationRegistry.class);
+		}
+		catch (NoSuchBeanDefinitionException ex) {
+		}
 	}
 
 	@Override
@@ -373,6 +383,13 @@ public final class WebSecurity extends AbstractConfiguredSecurityBuilder<Filter,
 		this.servletContext = servletContext;
 	}
 
+	FilterChainProxy.FilterChainDecorator getFilterChainDecorator() {
+		if (this.observationRegistry.isNoop()) {
+			return new FilterChainProxy.VirtualFilterChainDecorator();
+		}
+		return new ObservationFilterChainDecorator(this.observationRegistry);
+	}
+
 	/**
 	 * Allows registering {@link RequestMatcher} instances that should be ignored by
 	 * Spring Security.

config/src/main/java/org/springframework/security/config/annotation/web/reactive/WebFluxSecurityConfiguration.java

@@ -19,6 +19,8 @@ package org.springframework.security.config.annotation.web.reactive;
 import java.util.Arrays;
 import java.util.List;
 
+import io.micrometer.observation.ObservationRegistry;
+
 import org.springframework.beans.factory.annotation.Autowired;
 import org.springframework.beans.factory.config.BeanFactoryPostProcessor;
 import org.springframework.context.ApplicationContext;
@@ -28,6 +30,7 @@ import org.springframework.core.annotation.Order;
 import org.springframework.security.config.crypto.RsaKeyConversionServicePostProcessor;
 import org.springframework.security.config.web.server.ServerHttpSecurity;
 import org.springframework.security.web.reactive.result.view.CsrfRequestDataValueProcessor;
+import org.springframework.security.web.server.ObservationWebFilterChainDecorator;
 import org.springframework.security.web.server.SecurityWebFilterChain;
 import org.springframework.security.web.server.WebFilterChainProxy;
 import org.springframework.util.ClassUtils;
@@ -55,6 +58,8 @@ class WebFluxSecurityConfiguration {
 
 	private List<SecurityWebFilterChain> securityWebFilterChains;
 
+	private ObservationRegistry observationRegistry = ObservationRegistry.NOOP;
+
 	@Autowired
 	ApplicationContext context;
 
@@ -63,10 +68,19 @@ class WebFluxSecurityConfiguration {
 		this.securityWebFilterChains = securityWebFilterChains;
 	}
 
+	@Autowired(required = false)
+	void setObservationRegistry(ObservationRegistry observationRegistry) {
+		this.observationRegistry = observationRegistry;
+	}
+
 	@Bean(SPRING_SECURITY_WEBFILTERCHAINFILTER_BEAN_NAME)
 	@Order(WEB_FILTER_CHAIN_FILTER_ORDER)
 	WebFilterChainProxy springSecurityWebFilterChainFilter() {
-		return new WebFilterChainProxy(getSecurityWebFilterChains());
+		WebFilterChainProxy proxy = new WebFilterChainProxy(getSecurityWebFilterChains());
+		if (!this.observationRegistry.isNoop()) {
+			proxy.setFilterChainDecorator(new ObservationWebFilterChainDecorator(this.observationRegistry));
+		}
+		return proxy;
 	}
 
 	@Bean(name = AbstractView.REQUEST_DATA_VALUE_PROCESSOR_BEAN_NAME)

config/src/main/java/org/springframework/security/config/http/HttpSecurityBeanDefinitionParser.java

@@ -56,6 +56,7 @@ import org.springframework.security.config.Elements;
 import org.springframework.security.config.authentication.AuthenticationManagerFactoryBean;
 import org.springframework.security.web.DefaultSecurityFilterChain;
 import org.springframework.security.web.FilterChainProxy;
+import org.springframework.security.web.ObservationFilterChainDecorator;
 import org.springframework.security.web.PortResolverImpl;
 import org.springframework.security.web.util.matcher.AnyRequestMatcher;
 import org.springframework.util.StringUtils;
@@ -363,6 +364,10 @@ public class HttpSecurityBeanDefinitionParser implements BeanDefinitionParser {
 		fcpBldr.getRawBeanDefinition().setSource(source);
 		fcpBldr.addConstructorArgReference(BeanIds.FILTER_CHAINS);
 		fcpBldr.addPropertyValue("filterChainValidator", new RootBeanDefinition(DefaultFilterChainValidator.class));
+		BeanDefinition filterChainDecorator = BeanDefinitionBuilder
+				.rootBeanDefinition(FilterChainDecoratorFactory.class)
+				.addPropertyValue("observationRegistry", getObservationRegistry(element)).getBeanDefinition();
+		fcpBldr.addPropertyValue("filterChainDecorator", filterChainDecorator);
 		BeanDefinition fcpBean = fcpBldr.getBeanDefinition();
 		pc.registerBeanComponent(new BeanComponentDefinition(fcpBean, BeanIds.FILTER_CHAIN_PROXY));
 		registry.registerAlias(BeanIds.FILTER_CHAIN_PROXY, BeanIds.SPRING_SECURITY_FILTER_CHAIN);
@@ -509,4 +514,28 @@ public class HttpSecurityBeanDefinitionParser implements BeanDefinitionParser {
 
 	}
 
+	public static final class FilterChainDecoratorFactory
+			implements FactoryBean<FilterChainProxy.FilterChainDecorator> {
+
+		private ObservationRegistry observationRegistry = ObservationRegistry.NOOP;
+
+		@Override
+		public FilterChainProxy.FilterChainDecorator getObject() throws Exception {
+			if (this.observationRegistry.isNoop()) {
+				return new FilterChainProxy.VirtualFilterChainDecorator();
+			}
+			return new ObservationFilterChainDecorator(this.observationRegistry);
+		}
+
+		@Override
+		public Class<?> getObjectType() {
+			return FilterChainProxy.FilterChainDecorator.class;
+		}
+
+		public void setObservationRegistry(ObservationRegistry registry) {
+			this.observationRegistry = registry;
+		}
+
+	}
+
 }

config/src/test/java/org/springframework/security/config/annotation/web/configurers/HttpSecurityObservationTests.java

@@ -0,0 +1,115 @@
+/*
+ * Copyright 2002-2022 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.security.config.annotation.web.configurers;
+
+import java.util.Iterator;
+
+import io.micrometer.observation.Observation;
+import io.micrometer.observation.ObservationHandler;
+import io.micrometer.observation.ObservationRegistry;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.ExtendWith;
+import org.mockito.ArgumentCaptor;
+
+import org.springframework.beans.factory.annotation.Autowired;
+import org.springframework.context.annotation.Bean;
+import org.springframework.context.annotation.Configuration;
+import org.springframework.security.config.annotation.web.builders.HttpSecurity;
+import org.springframework.security.config.annotation.web.configuration.EnableWebSecurity;
+import org.springframework.security.config.test.SpringTestContext;
+import org.springframework.security.config.test.SpringTestContextExtension;
+import org.springframework.security.core.userdetails.User;
+import org.springframework.security.core.userdetails.UserDetailsService;
+import org.springframework.security.provisioning.InMemoryUserDetailsManager;
+import org.springframework.security.web.SecurityFilterChain;
+import org.springframework.test.web.servlet.MockMvc;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.mockito.ArgumentMatchers.any;
+import static org.mockito.BDDMockito.given;
+import static org.mockito.Mockito.mock;
+import static org.mockito.Mockito.times;
+import static org.mockito.Mockito.verify;
+import static org.springframework.security.config.Customizer.withDefaults;
+import static org.springframework.security.test.web.servlet.request.SecurityMockMvcRequestPostProcessors.httpBasic;
+import static org.springframework.test.web.servlet.request.MockMvcRequestBuilders.get;
+import static org.springframework.test.web.servlet.result.MockMvcResultMatchers.status;
+
+/**
+ * @author Josh Cummings
+ *
+ */
+@ExtendWith(SpringTestContextExtension.class)
+public class HttpSecurityObservationTests {
+
+	@Autowired
+	MockMvc mvc;
+
+	public final SpringTestContext spring = new SpringTestContext(this);
+
+	@Test
+	public void getWhenUsingObservationRegistryThenObservesRequest() throws Exception {
+		this.spring.register(ObservationRegistryConfig.class).autowire();
+		// @formatter:off
+		this.mvc.perform(get("/").with(httpBasic("user", "password")))
+				.andExpect(status().isNotFound());
+		// @formatter:on
+		ObservationHandler<Observation.Context> handler = this.spring.getContext().getBean(ObservationHandler.class);
+		ArgumentCaptor<Observation.Context> captor = ArgumentCaptor.forClass(Observation.Context.class);
+		verify(handler, times(5)).onStart(captor.capture());
+		Iterator<Observation.Context> contexts = captor.getAllValues().iterator();
+		assertThat(contexts.next().getContextualName()).isEqualTo("spring.security.http.chains.before");
+		assertThat(contexts.next().getName()).isEqualTo("spring.security.authentications");
+		assertThat(contexts.next().getName()).isEqualTo("spring.security.authorizations");
+		assertThat(contexts.next().getName()).isEqualTo("spring.security.http.secured.requests");
+		assertThat(contexts.next().getContextualName()).isEqualTo("spring.security.http.chains.after");
+	}
+
+	@EnableWebSecurity
+	@Configuration
+	static class ObservationRegistryConfig {
+
+		private ObservationHandler<Observation.Context> handler = mock(ObservationHandler.class);
+
+		@Bean
+		SecurityFilterChain app(HttpSecurity http) throws Exception {
+			http.httpBasic(withDefaults()).authorizeHttpRequests((requests) -> requests.anyRequest().authenticated());
+			return http.build();
+		}
+
+		@Bean
+		UserDetailsService userDetailsService() {
+			return new InMemoryUserDetailsManager(
+					User.withDefaultPasswordEncoder().username("user").password("password").authorities("app").build());
+		}
+
+		@Bean
+		ObservationHandler<Observation.Context> observationHandler() {
+			return this.handler;
+		}
+
+		@Bean
+		ObservationRegistry observationRegistry() {
+			given(this.handler.supportsContext(any())).willReturn(true);
+			ObservationRegistry registry = ObservationRegistry.create();
+			registry.observationConfig().observationHandler(this.handler);
+			return registry;
+		}
+
+	}
+
+}

config/src/test/java/org/springframework/security/config/http/HttpConfigTests.java

@@ -16,13 +16,20 @@
 
 package org.springframework.security.config.http;
 
+import java.util.Iterator;
+
+import io.micrometer.observation.Observation;
+import io.micrometer.observation.ObservationHandler;
+import io.micrometer.observation.ObservationRegistry;
 import jakarta.servlet.http.HttpServletRequest;
 import jakarta.servlet.http.HttpServletResponse;
 import jakarta.servlet.http.HttpServletResponseWrapper;
 import org.apache.http.HttpStatus;
 import org.junit.jupiter.api.Test;
 import org.junit.jupiter.api.extension.ExtendWith;
+import org.mockito.ArgumentCaptor;
 
+import org.springframework.beans.factory.FactoryBean;
 import org.springframework.beans.factory.annotation.Autowired;
 import org.springframework.mock.web.MockHttpServletRequest;
 import org.springframework.mock.web.MockHttpServletResponse;
@@ -36,7 +43,10 @@ import org.springframework.test.web.servlet.MockMvc;
 import static org.assertj.core.api.Assertions.assertThat;
 import static org.mockito.ArgumentMatchers.any;
 import static org.mockito.BDDMockito.given;
+import static org.mockito.Mockito.mock;
+import static org.mockito.Mockito.times;
 import static org.mockito.Mockito.verify;
+import static org.springframework.security.test.web.servlet.request.SecurityMockMvcRequestPostProcessors.httpBasic;
 import static org.springframework.test.web.servlet.request.MockMvcRequestBuilders.get;
 import static org.springframework.test.web.servlet.result.MockMvcResultMatchers.redirectedUrl;
 import static org.springframework.test.web.servlet.result.MockMvcResultMatchers.status;
@@ -101,6 +111,24 @@ public class HttpConfigTests {
 		assertThat(response.getRedirectedUrl()).isEqualTo("http://localhost/login");
 	}
 
+	@Test
+	public void getWhenUsingObservationRegistryThenObservesRequest() throws Exception {
+		this.spring.configLocations(this.xml("WithObservationRegistry")).autowire();
+		// @formatter:off
+		this.mvc.perform(get("/").with(httpBasic("user", "password")))
+				.andExpect(status().isNotFound());
+		// @formatter:on
+		ObservationHandler<Observation.Context> handler = this.spring.getContext().getBean(ObservationHandler.class);
+		ArgumentCaptor<Observation.Context> captor = ArgumentCaptor.forClass(Observation.Context.class);
+		verify(handler, times(5)).onStart(captor.capture());
+		Iterator<Observation.Context> contexts = captor.getAllValues().iterator();
+		assertThat(contexts.next().getContextualName()).isEqualTo("spring.security.http.chains.before");
+		assertThat(contexts.next().getName()).isEqualTo("spring.security.authentications");
+		assertThat(contexts.next().getName()).isEqualTo("spring.security.authorizations");
+		assertThat(contexts.next().getName()).isEqualTo("spring.security.http.secured.requests");
+		assertThat(contexts.next().getContextualName()).isEqualTo("spring.security.http.chains.after");
+	}
+
 	private String xml(String configName) {
 		return CONFIG_LOCATION_PREFIX + "-" + configName + ".xml";
 	}
@@ -133,4 +161,27 @@ public class HttpConfigTests {
 
 	}
 
+	public static final class MockObservationRegistry implements FactoryBean<ObservationRegistry> {
+
+		private ObservationHandler<Observation.Context> handler = mock(ObservationHandler.class);
+
+		@Override
+		public ObservationRegistry getObject() {
+			ObservationRegistry registry = ObservationRegistry.create();
+			registry.observationConfig().observationHandler(this.handler);
+			given(this.handler.supportsContext(any())).willReturn(true);
+			return registry;
+		}
+
+		@Override
+		public Class<?> getObjectType() {
+			return ObservationRegistry.class;
+		}
+
+		public void setHandler(ObservationHandler<Observation.Context> handler) {
+			this.handler = handler;
+		}
+
+	}
+
 }

config/src/test/resources/org/springframework/security/config/http/HttpConfigTests-WithObservationRegistry.xml

@@ -0,0 +1,40 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<!--
+  ~ Copyright 2002-2018 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.
+  -->
+
+<b:beans xmlns:b="http://www.springframework.org/schema/beans"
+		xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance"
+		xmlns="http://www.springframework.org/schema/security"
+		xsi:schemaLocation="
+			http://www.springframework.org/schema/security
+			https://www.springframework.org/schema/security/spring-security.xsd
+			http://www.springframework.org/schema/beans
+			https://www.springframework.org/schema/beans/spring-beans.xsd">
+
+	<http auto-config="true" observation-registry-ref="ref" use-authorization-manager="true">
+		<intercept-url pattern="/**" access="hasRole('USER')"/>
+	</http>
+
+	<b:bean name="handler" class="org.mockito.Mockito" factory-method="mock">
+		<b:constructor-arg value="io.micrometer.observation.ObservationHandler"/>
+	</b:bean>
+
+	<b:bean name="ref" class="org.springframework.security.config.http.HttpConfigTests.MockObservationRegistry">
+		<b:property name="handler" ref="handler"/>
+	</b:bean>
+
+	<b:import resource="userservice.xml"/>
+</b:beans>

web/src/main/java/org/springframework/security/web/FilterChainProxy.java

@@ -160,6 +160,8 @@ public class FilterChainProxy extends GenericFilterBean {
 
 	private ThrowableAnalyzer throwableAnalyzer = new ThrowableAnalyzer();
 
+	private FilterChainDecorator filterChainDecorator = new VirtualFilterChainDecorator();
+
 	public FilterChainProxy() {
 	}
 
@@ -214,14 +216,21 @@ public class FilterChainProxy extends GenericFilterBean {
 				logger.trace(LogMessage.of(() -> "No security for " + requestLine(firewallRequest)));
 			}
 			firewallRequest.reset();
-			chain.doFilter(firewallRequest, firewallResponse);
+			this.filterChainDecorator.decorate(chain).doFilter(firewallRequest, firewallResponse);
 			return;
 		}
 		if (logger.isDebugEnabled()) {
 			logger.debug(LogMessage.of(() -> "Securing " + requestLine(firewallRequest)));
 		}
-		VirtualFilterChain virtualFilterChain = new VirtualFilterChain(firewallRequest, chain, filters);
+		FilterChain reset = (req, res) -> {
-		virtualFilterChain.doFilter(firewallRequest, firewallResponse);
+			if (logger.isDebugEnabled()) {
+				logger.debug(LogMessage.of(() -> "Secured " + requestLine(firewallRequest)));
+			}
+			// Deactivate path stripping as we exit the security filter chain
+			firewallRequest.reset();
+			chain.doFilter(req, res);
+		};
+		this.filterChainDecorator.decorate(reset, filters).doFilter(firewallRequest, firewallResponse);
 	}
 
 	/**
@@ -249,7 +258,7 @@ public class FilterChainProxy extends GenericFilterBean {
 	 * @return matching filter list
 	 */
 	public List<Filter> getFilters(String url) {
-		return getFilters(this.firewall.getFirewalledRequest((new FilterInvocation(url, "GET").getRequest())));
+		return getFilters(this.firewall.getFirewalledRequest(new FilterInvocation(url, "GET").getRequest()));
 	}
 
 	/**
@@ -281,6 +290,20 @@ public class FilterChainProxy extends GenericFilterBean {
 		this.filterChainValidator = filterChainValidator;
 	}
 
+	/**
+	 * Used to decorate the original {@link FilterChain} for each request
+	 *
+	 * <p>
+	 * By default, this decorates the filter chain with a {@link VirtualFilterChain} that
+	 * iterates through security filters and then delegates to the original chain
+	 * @param filterChainDecorator the strategy for constructing the filter chain
+	 * @since 6.0
+	 */
+	public void setFilterChainDecorator(FilterChainDecorator filterChainDecorator) {
+		Assert.notNull(filterChainDecorator, "filterChainDecorator cannot be null");
+		this.filterChainDecorator = filterChainDecorator;
+	}
+
 	/**
 	 * Sets the "firewall" implementation which will be used to validate and wrap (or
 	 * potentially reject) the incoming requests. The default implementation should be
@@ -326,36 +349,27 @@ public class FilterChainProxy extends GenericFilterBean {
 
 		private final List<Filter> additionalFilters;
 
-		private final FirewalledRequest firewalledRequest;
-
 		private final int size;
 
 		private int currentPosition = 0;
 
-		private VirtualFilterChain(FirewalledRequest firewalledRequest, FilterChain chain,
+		private VirtualFilterChain(FilterChain chain, List<Filter> additionalFilters) {
-				List<Filter> additionalFilters) {
 			this.originalChain = chain;
 			this.additionalFilters = additionalFilters;
 			this.size = additionalFilters.size();
-			this.firewalledRequest = firewalledRequest;
 		}
 
 		@Override
 		public void doFilter(ServletRequest request, ServletResponse response) throws IOException, ServletException {
 			if (this.currentPosition == this.size) {
-				if (logger.isDebugEnabled()) {
-					logger.debug(LogMessage.of(() -> "Secured " + requestLine(this.firewalledRequest)));
-				}
-				// Deactivate path stripping as we exit the security filter chain
-				this.firewalledRequest.reset();
 				this.originalChain.doFilter(request, response);
 				return;
 			}
 			this.currentPosition++;
 			Filter nextFilter = this.additionalFilters.get(this.currentPosition - 1);
 			if (logger.isTraceEnabled()) {
-				logger.trace(LogMessage.format("Invoking %s (%d/%d)", nextFilter.getClass().getSimpleName(),
+				String name = nextFilter.getClass().getSimpleName();
-						this.currentPosition, this.size));
+				logger.trace(LogMessage.format("Invoking %s (%d/%d)", name, this.currentPosition, this.size));
 			}
 			nextFilter.doFilter(request, response, this);
 		}
@@ -376,4 +390,61 @@ public class FilterChainProxy extends GenericFilterBean {
 
 	}
 
+	/**
+	 * A strategy for decorating the provided filter chain with one that accounts for the
+	 * {@link SecurityFilterChain} for a given request.
+	 *
+	 * @author Josh Cummings
+	 * @since 6.0
+	 */
+	public interface FilterChainDecorator {
+
+		/**
+		 * Provide a new {@link FilterChain} that accounts for needed security
+		 * considerations when there are no security filters.
+		 * @param original the original {@link FilterChain}
+		 * @return a security-enabled {@link FilterChain}
+		 */
+		default FilterChain decorate(FilterChain original) {
+			return decorate(original, Collections.emptyList());
+		}
+
+		/**
+		 * Provide a new {@link FilterChain} that accounts for the provided filters as
+		 * well as teh original filter chain.
+		 * @param original the original {@link FilterChain}
+		 * @param filters the security filters
+		 * @return a security-enabled {@link FilterChain} that includes the provided
+		 * filters
+		 */
+		FilterChain decorate(FilterChain original, List<Filter> filters);
+
+	}
+
+	/**
+	 * A {@link FilterChainDecorator} that uses the {@link VirtualFilterChain}
+	 *
+	 * @author Josh Cummings
+	 * @since 6.0
+	 */
+	public static final class VirtualFilterChainDecorator implements FilterChainDecorator {
+
+		/**
+		 * {@inheritDoc}
+		 */
+		@Override
+		public FilterChain decorate(FilterChain original) {
+			return original;
+		}
+
+		/**
+		 * {@inheritDoc}
+		 */
+		@Override
+		public FilterChain decorate(FilterChain original, List<Filter> filters) {
+			return new VirtualFilterChain(original, filters);
+		}
+
+	}
+
 }

web/src/main/java/org/springframework/security/web/ObservationFilterChainDecorator.java

@@ -0,0 +1,525 @@
+/*
+ * Copyright 2002-2022 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.security.web;
+
+import java.io.IOException;
+import java.util.ArrayList;
+import java.util.Arrays;
+import java.util.Iterator;
+import java.util.List;
+import java.util.concurrent.atomic.AtomicReference;
+
+import io.micrometer.common.KeyValues;
+import io.micrometer.observation.Observation;
+import io.micrometer.observation.ObservationConvention;
+import io.micrometer.observation.ObservationRegistry;
+import jakarta.servlet.Filter;
+import jakarta.servlet.FilterChain;
+import jakarta.servlet.ServletException;
+import jakarta.servlet.ServletRequest;
+import jakarta.servlet.ServletResponse;
+import jakarta.servlet.http.HttpServletRequest;
+import org.apache.commons.logging.Log;
+import org.apache.commons.logging.LogFactory;
+
+import org.springframework.core.log.LogMessage;
+import org.springframework.security.web.util.UrlUtils;
+
+/**
+ * A {@link org.springframework.security.web.server.FilterChainProxy.FilterChainDecorator}
+ * that wraps the chain in before and after observations
+ *
+ * @author Josh Cummings
+ * @since 6.0
+ */
+public final class ObservationFilterChainDecorator implements FilterChainProxy.FilterChainDecorator {
+
+	private static final Log logger = LogFactory.getLog(FilterChainProxy.class);
+
+	private static final String ATTRIBUTE = ObservationFilterChainDecorator.class + ".observation";
+
+	static final String UNSECURED_OBSERVATION_NAME = "spring.security.http.unsecured.requests";
+
+	static final String SECURED_OBSERVATION_NAME = "spring.security.http.secured.requests";
+
+	private final ObservationRegistry registry;
+
+	public ObservationFilterChainDecorator(ObservationRegistry registry) {
+		this.registry = registry;
+	}
+
+	@Override
+	public FilterChain decorate(FilterChain original) {
+		return wrapUnsecured(original);
+	}
+
+	@Override
+	public FilterChain decorate(FilterChain original, List<Filter> filters) {
+		return new VirtualFilterChain(wrapSecured(original), wrap(filters));
+	}
+
+	private FilterChain wrapSecured(FilterChain original) {
+		return (req, res) -> {
+			AroundFilterObservation parent = observation((HttpServletRequest) req);
+			Observation observation = Observation.createNotStarted(SECURED_OBSERVATION_NAME, this.registry);
+			parent.wrap(FilterObservation.create(observation).wrap(original)).doFilter(req, res);
+		};
+	}
+
+	private FilterChain wrapUnsecured(FilterChain original) {
+		return (req, res) -> {
+			Observation observation = Observation.createNotStarted(UNSECURED_OBSERVATION_NAME, this.registry);
+			FilterObservation.create(observation).wrap(original).doFilter(req, res);
+		};
+	}
+
+	private List<ObservationFilter> wrap(List<Filter> filters) {
+		int size = filters.size();
+		List<ObservationFilter> observableFilters = new ArrayList<>();
+		int position = 1;
+		for (Filter filter : filters) {
+			observableFilters.add(new ObservationFilter(this.registry, filter, position, size));
+			position++;
+		}
+		return observableFilters;
+	}
+
+	static AroundFilterObservation observation(HttpServletRequest request) {
+		return (AroundFilterObservation) request.getAttribute(ATTRIBUTE);
+	}
+
+	private static final class VirtualFilterChain implements FilterChain {
+
+		private final FilterChain originalChain;
+
+		private final List<ObservationFilter> additionalFilters;
+
+		private final int size;
+
+		private int currentPosition = 0;
+
+		private VirtualFilterChain(FilterChain chain, List<ObservationFilter> additionalFilters) {
+			this.originalChain = chain;
+			this.additionalFilters = additionalFilters;
+			this.size = additionalFilters.size();
+		}
+
+		@Override
+		public void doFilter(ServletRequest request, ServletResponse response) throws IOException, ServletException {
+			if (this.currentPosition == this.size) {
+				this.originalChain.doFilter(request, response);
+				return;
+			}
+			this.currentPosition++;
+			ObservationFilter nextFilter = this.additionalFilters.get(this.currentPosition - 1);
+			if (logger.isTraceEnabled()) {
+				String name = nextFilter.getName();
+				logger.trace(LogMessage.format("Invoking %s (%d/%d)", name, this.currentPosition, this.size));
+			}
+			nextFilter.doFilter(request, response, this);
+		}
+
+	}
+
+	static final class ObservationFilter implements Filter {
+
+		private final ObservationRegistry registry;
+
+		private final FilterChainObservationConvention convention = new FilterChainObservationConvention();
+
+		private final Filter filter;
+
+		private final String name;
+
+		private final int position;
+
+		private final int size;
+
+		ObservationFilter(ObservationRegistry registry, Filter filter, int position, int size) {
+			this.registry = registry;
+			this.filter = filter;
+			this.name = filter.getClass().getSimpleName();
+			this.position = position;
+			this.size = size;
+		}
+
+		String getName() {
+			return this.name;
+		}
+
+		@Override
+		public void doFilter(ServletRequest request, ServletResponse response, FilterChain chain)
+				throws IOException, ServletException {
+			if (this.position == 1) {
+				AroundFilterObservation parent = parent((HttpServletRequest) request);
+				parent.wrap(this::wrapFilter).doFilter(request, response, chain);
+			}
+			else {
+				wrapFilter(request, response, chain);
+			}
+		}
+
+		private void wrapFilter(ServletRequest request, ServletResponse response, FilterChain chain)
+				throws IOException, ServletException {
+			AroundFilterObservation parent = observation((HttpServletRequest) request);
+			FilterChainObservationContext parentBefore = (FilterChainObservationContext) parent.before().getContext();
+			parentBefore.setChainSize(this.size);
+			parentBefore.setFilterName(this.name);
+			parentBefore.setChainPosition(this.position);
+			this.filter.doFilter(request, response, chain);
+			parent.start();
+			FilterChainObservationContext parentAfter = (FilterChainObservationContext) parent.after().getContext();
+			parentAfter.setChainSize(this.size);
+			parentAfter.setFilterName(this.name);
+			parentAfter.setChainPosition(this.size - this.position + 1);
+		}
+
+		private AroundFilterObservation parent(HttpServletRequest request) {
+			FilterChainObservationContext beforeContext = FilterChainObservationContext.before(request);
+			FilterChainObservationContext afterContext = FilterChainObservationContext.after(request);
+			Observation before = Observation.createNotStarted(this.convention, () -> beforeContext, this.registry);
+			Observation after = Observation.createNotStarted(this.convention, () -> afterContext, this.registry);
+			AroundFilterObservation parent = AroundFilterObservation.create(before, after);
+			request.setAttribute(ATTRIBUTE, parent);
+			return parent;
+		}
+
+	}
+
+	interface AroundFilterObservation extends FilterObservation {
+
+		AroundFilterObservation NOOP = new AroundFilterObservation() {
+		};
+
+		static AroundFilterObservation create(Observation before, Observation after) {
+			if (before.isNoop() || after.isNoop()) {
+				return NOOP;
+			}
+			return new SimpleAroundFilterObservation(before, after);
+		}
+
+		default Observation before() {
+			return Observation.NOOP;
+		}
+
+		default Observation after() {
+			return Observation.NOOP;
+		}
+
+		class SimpleAroundFilterObservation implements AroundFilterObservation {
+
+			private final Iterator<Observation> observations;
+
+			private final Observation before;
+
+			private final Observation after;
+
+			private final AtomicReference<Observation.Scope> currentScope = new AtomicReference<>(null);
+
+			SimpleAroundFilterObservation(Observation before, Observation after) {
+				this.before = before;
+				this.after = after;
+				this.observations = Arrays.asList(before, after).iterator();
+			}
+
+			@Override
+			public void start() {
+				if (this.observations.hasNext()) {
+					stop();
+					Observation observation = this.observations.next();
+					observation.start();
+					Observation.Scope scope = observation.openScope();
+					this.currentScope.set(scope);
+				}
+			}
+
+			@Override
+			public void error(Throwable ex) {
+				Observation.Scope scope = this.currentScope.get();
+				if (scope == null) {
+					return;
+				}
+				scope.close();
+				scope.getCurrentObservation().error(ex);
+			}
+
+			@Override
+			public void stop() {
+				Observation.Scope scope = this.currentScope.getAndSet(null);
+				if (scope == null) {
+					return;
+				}
+				scope.close();
+				scope.getCurrentObservation().stop();
+			}
+
+			@Override
+			public Filter wrap(Filter filter) {
+				return (request, response, chain) -> {
+					start();
+					try {
+						filter.doFilter(request, response, chain);
+					}
+					catch (Throwable ex) {
+						error(ex);
+						throw ex;
+					}
+					finally {
+						stop();
+					}
+				};
+			}
+
+			@Override
+			public FilterChain wrap(FilterChain chain) {
+				return (request, response) -> {
+					stop();
+					try {
+						chain.doFilter(request, response);
+					}
+					finally {
+						start();
+					}
+				};
+			}
+
+			@Override
+			public Observation before() {
+				return this.before;
+			}
+
+			@Override
+			public Observation after() {
+				return this.after;
+			}
+
+		}
+
+	}
+
+	interface FilterObservation {
+
+		FilterObservation NOOP = new FilterObservation() {
+		};
+
+		static FilterObservation create(Observation observation) {
+			if (observation.isNoop()) {
+				return NOOP;
+			}
+			return new SimpleFilterObservation(observation);
+		}
+
+		default void start() {
+		}
+
+		default void error(Throwable ex) {
+		}
+
+		default void stop() {
+		}
+
+		default Filter wrap(Filter filter) {
+			return filter;
+		}
+
+		default FilterChain wrap(FilterChain chain) {
+			return chain;
+		}
+
+		class SimpleFilterObservation implements FilterObservation {
+
+			private final Observation observation;
+
+			SimpleFilterObservation(Observation observation) {
+				this.observation = observation;
+			}
+
+			@Override
+			public void start() {
+				this.observation.start();
+			}
+
+			@Override
+			public void error(Throwable ex) {
+				this.observation.error(ex);
+			}
+
+			@Override
+			public void stop() {
+				this.observation.stop();
+			}
+
+			@Override
+			public Filter wrap(Filter filter) {
+				if (this.observation.isNoop()) {
+					return filter;
+				}
+				return (request, response, chain) -> {
+					this.observation.start();
+					try (Observation.Scope scope = this.observation.openScope()) {
+						filter.doFilter(request, response, chain);
+					}
+					catch (Throwable ex) {
+						this.observation.error(ex);
+						throw ex;
+					}
+					finally {
+						this.observation.stop();
+					}
+				};
+			}
+
+			@Override
+			public FilterChain wrap(FilterChain chain) {
+				if (this.observation.isNoop()) {
+					return chain;
+				}
+				return (request, response) -> {
+					this.observation.start();
+					try (Observation.Scope scope = this.observation.openScope()) {
+						chain.doFilter(request, response);
+					}
+					catch (Throwable ex) {
+						this.observation.error(ex);
+						throw ex;
+					}
+					finally {
+						this.observation.stop();
+					}
+				};
+			}
+
+		}
+
+	}
+
+	static final class FilterChainObservationContext extends Observation.Context {
+
+		private final ServletRequest request;
+
+		private final String filterSection;
+
+		private String filterName;
+
+		private int chainPosition;
+
+		private int chainSize;
+
+		private FilterChainObservationContext(ServletRequest request, String filterSection) {
+			this.filterSection = filterSection;
+			this.request = request;
+		}
+
+		static FilterChainObservationContext before(ServletRequest request) {
+			return new FilterChainObservationContext(request, "before");
+		}
+
+		static FilterChainObservationContext after(ServletRequest request) {
+			return new FilterChainObservationContext(request, "after");
+		}
+
+		@Override
+		public void setName(String name) {
+			super.setName(name);
+			if (name != null) {
+				setContextualName(name + "." + this.filterSection);
+			}
+		}
+
+		String getRequestLine() {
+			return requestLine((HttpServletRequest) this.request);
+		}
+
+		String getFilterSection() {
+			return this.filterSection;
+		}
+
+		String getFilterName() {
+			return this.filterName;
+		}
+
+		void setFilterName(String filterName) {
+			this.filterName = filterName;
+		}
+
+		int getChainPosition() {
+			return this.chainPosition;
+		}
+
+		void setChainPosition(int chainPosition) {
+			this.chainPosition = chainPosition;
+		}
+
+		int getChainSize() {
+			return this.chainSize;
+		}
+
+		void setChainSize(int chainSize) {
+			this.chainSize = chainSize;
+		}
+
+		private static String requestLine(HttpServletRequest request) {
+			return request.getMethod() + " " + UrlUtils.buildRequestUrl(request);
+		}
+
+	}
+
+	static final class FilterChainObservationConvention
+			implements ObservationConvention<FilterChainObservationContext> {
+
+		static final String CHAIN_OBSERVATION_NAME = "spring.security.http.chains";
+
+		private static final String REQUEST_LINE_NAME = "request.line";
+
+		private static final String CHAIN_POSITION_NAME = "chain.position";
+
+		private static final String CHAIN_SIZE_NAME = "chain.size";
+
+		private static final String FILTER_SECTION_NAME = "filter.section";
+
+		private static final String FILTER_NAME = "current.filter.name";
+
+		@Override
+		public String getName() {
+			return CHAIN_OBSERVATION_NAME;
+		}
+
+		@Override
+		public KeyValues getLowCardinalityKeyValues(FilterChainObservationContext context) {
+			KeyValues kv = KeyValues.of(CHAIN_SIZE_NAME, String.valueOf(context.getChainSize()))
+					.and(CHAIN_POSITION_NAME, String.valueOf(context.getChainPosition()))
+					.and(FILTER_SECTION_NAME, context.getFilterSection());
+			if (context.getFilterName() != null) {
+				kv = kv.and(FILTER_NAME, context.getFilterName());
+			}
+			return kv;
+		}
+
+		@Override
+		public KeyValues getHighCardinalityKeyValues(FilterChainObservationContext context) {
+			String requestLine = context.getRequestLine();
+			return KeyValues.of(REQUEST_LINE_NAME, requestLine);
+		}
+
+		@Override
+		public boolean supportsContext(Observation.Context context) {
+			return context instanceof FilterChainObservationContext;
+		}
+
+	}
+
+}

web/src/main/java/org/springframework/security/web/server/ObservationWebFilterChainDecorator.java

@@ -0,0 +1,531 @@
+/*
+ * Copyright 2002-2022 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.security.web.server;
+
+import java.util.ArrayList;
+import java.util.Arrays;
+import java.util.Iterator;
+import java.util.List;
+import java.util.ListIterator;
+import java.util.concurrent.atomic.AtomicReference;
+
+import io.micrometer.common.KeyValues;
+import io.micrometer.observation.Observation;
+import io.micrometer.observation.ObservationConvention;
+import io.micrometer.observation.ObservationRegistry;
+import reactor.core.publisher.Mono;
+
+import org.springframework.lang.Nullable;
+import org.springframework.util.Assert;
+import org.springframework.web.server.ServerWebExchange;
+import org.springframework.web.server.WebFilter;
+import org.springframework.web.server.WebFilterChain;
+import org.springframework.web.server.WebHandler;
+
+/**
+ * A
+ * {@link org.springframework.security.web.server.WebFilterChainProxy.WebFilterChainDecorator}
+ * that wraps the chain in before and after observations
+ *
+ * @author Josh Cummings
+ * @since 6.0
+ */
+public final class ObservationWebFilterChainDecorator implements WebFilterChainProxy.WebFilterChainDecorator {
+
+	private static final String ATTRIBUTE = ObservationWebFilterChainDecorator.class + ".observation";
+
+	static final String UNSECURED_OBSERVATION_NAME = "spring.security.http.unsecured.requests";
+
+	static final String SECURED_OBSERVATION_NAME = "spring.security.http.secured.requests";
+
+	private final ObservationRegistry registry;
+
+	public ObservationWebFilterChainDecorator(ObservationRegistry registry) {
+		this.registry = registry;
+	}
+
+	@Override
+	public WebFilterChain decorate(WebFilterChain original) {
+		return wrapUnsecured(original);
+	}
+
+	@Override
+	public WebFilterChain decorate(WebFilterChain original, List<WebFilter> filters) {
+		return new ObservationWebFilterChain(wrapSecured(original)::filter, wrap(filters));
+	}
+
+	private static AroundWebFilterObservation observation(ServerWebExchange exchange) {
+		return exchange.getAttribute(ATTRIBUTE);
+	}
+
+	private WebFilterChain wrapSecured(WebFilterChain original) {
+		return (exchange) -> {
+			AroundWebFilterObservation parent = observation(exchange);
+			Observation observation = Observation.createNotStarted(SECURED_OBSERVATION_NAME, this.registry);
+			return parent.wrap(WebFilterObservation.create(observation).wrap(original)).filter(exchange);
+		};
+	}
+
+	private WebFilterChain wrapUnsecured(WebFilterChain original) {
+		return (exchange) -> {
+			Observation observation = Observation.createNotStarted(UNSECURED_OBSERVATION_NAME, this.registry);
+			return WebFilterObservation.create(observation).wrap(original).filter(exchange);
+		};
+	}
+
+	private List<ObservationWebFilter> wrap(List<WebFilter> filters) {
+		int size = filters.size();
+		List<ObservationWebFilter> observableFilters = new ArrayList<>();
+		int position = 1;
+		for (WebFilter filter : filters) {
+			observableFilters.add(new ObservationWebFilter(this.registry, filter, position, size));
+			position++;
+		}
+		return observableFilters;
+	}
+
+	static class ObservationWebFilterChain implements WebFilterChain {
+
+		private final WebHandler handler;
+
+		@Nullable
+		private final ObservationWebFilter currentFilter;
+
+		@Nullable
+		private final ObservationWebFilterChain chain;
+
+		/**
+		 * Public constructor with the list of filters and the target handler to use.
+		 * @param handler the target handler
+		 * @param filters the filters ahead of the handler
+		 * @since 5.1
+		 */
+		ObservationWebFilterChain(WebHandler handler, List<ObservationWebFilter> filters) {
+			Assert.notNull(handler, "WebHandler is required");
+			this.handler = handler;
+			ObservationWebFilterChain chain = initChain(filters, handler);
+			this.currentFilter = chain.currentFilter;
+			this.chain = chain.chain;
+		}
+
+		private static ObservationWebFilterChain initChain(List<ObservationWebFilter> filters, WebHandler handler) {
+			ObservationWebFilterChain chain = new ObservationWebFilterChain(handler, null, null);
+			ListIterator<? extends ObservationWebFilter> iterator = filters.listIterator(filters.size());
+			while (iterator.hasPrevious()) {
+				chain = new ObservationWebFilterChain(handler, iterator.previous(), chain);
+			}
+			return chain;
+		}
+
+		/**
+		 * Private constructor to represent one link in the chain.
+		 */
+		private ObservationWebFilterChain(WebHandler handler, @Nullable ObservationWebFilter currentFilter,
+				@Nullable ObservationWebFilterChain chain) {
+			this.currentFilter = currentFilter;
+			this.handler = handler;
+			this.chain = chain;
+		}
+
+		@Override
+		public Mono<Void> filter(ServerWebExchange exchange) {
+			return Mono.defer(() -> (this.currentFilter != null && this.chain != null)
+					? invokeFilter(this.currentFilter, this.chain, exchange) : this.handler.handle(exchange));
+		}
+
+		private Mono<Void> invokeFilter(ObservationWebFilter current, ObservationWebFilterChain chain,
+				ServerWebExchange exchange) {
+			String currentName = current.getName();
+			return current.filter(exchange, chain).checkpoint(currentName + " [DefaultWebFilterChain]");
+		}
+
+	}
+
+	static final class ObservationWebFilter implements WebFilter {
+
+		private final ObservationRegistry registry;
+
+		private final WebFilterChainObservationConvention convention = new WebFilterChainObservationConvention();
+
+		private final WebFilter filter;
+
+		private final String name;
+
+		private final int position;
+
+		private final int size;
+
+		ObservationWebFilter(ObservationRegistry registry, WebFilter filter, int position, int size) {
+			this.registry = registry;
+			this.filter = filter;
+			this.name = filter.getClass().getSimpleName();
+			this.position = position;
+			this.size = size;
+		}
+
+		String getName() {
+			return this.name;
+		}
+
+		@Override
+		public Mono<Void> filter(ServerWebExchange exchange, WebFilterChain chain) {
+			if (this.position == 1) {
+				AroundWebFilterObservation parent = parent(exchange);
+				return parent.wrap(this::wrapFilter).filter(exchange, chain);
+			}
+			else {
+				return wrapFilter(exchange, chain);
+			}
+		}
+
+		private Mono<Void> wrapFilter(ServerWebExchange exchange, WebFilterChain chain) {
+			AroundWebFilterObservation parent = observation(exchange);
+			WebFilterChainObservationContext parentBefore = (WebFilterChainObservationContext) parent.before()
+					.getContext();
+			parentBefore.setChainSize(this.size);
+			parentBefore.setFilterName(this.name);
+			parentBefore.setChainPosition(this.position);
+			return this.filter.filter(exchange, chain).doOnSuccess((result) -> {
+				parent.start();
+				WebFilterChainObservationContext parentAfter = (WebFilterChainObservationContext) parent.after()
+						.getContext();
+				parentAfter.setChainSize(this.size);
+				parentAfter.setFilterName(this.name);
+				parentAfter.setChainPosition(this.size - this.position + 1);
+			});
+		}
+
+		private AroundWebFilterObservation parent(ServerWebExchange exchange) {
+			WebFilterChainObservationContext beforeContext = WebFilterChainObservationContext.before(exchange);
+			WebFilterChainObservationContext afterContext = WebFilterChainObservationContext.after(exchange);
+			Observation before = Observation.createNotStarted(this.convention, () -> beforeContext, this.registry);
+			Observation after = Observation.createNotStarted(this.convention, () -> afterContext, this.registry);
+			AroundWebFilterObservation parent = AroundWebFilterObservation.create(before, after);
+			exchange.getAttributes().put(ATTRIBUTE, parent);
+			return parent;
+		}
+
+	}
+
+	interface AroundWebFilterObservation extends WebFilterObservation {
+
+		AroundWebFilterObservation NOOP = new AroundWebFilterObservation() {
+		};
+
+		static AroundWebFilterObservation create(Observation before, Observation after) {
+			if (before.isNoop() || after.isNoop()) {
+				return NOOP;
+			}
+			return new SimpleAroundWebFilterObservation(before, after);
+		}
+
+		default Observation before() {
+			return Observation.NOOP;
+		}
+
+		default Observation after() {
+			return Observation.NOOP;
+		}
+
+		class SimpleAroundWebFilterObservation implements AroundWebFilterObservation {
+
+			private final Iterator<Observation> observations;
+
+			private final Observation before;
+
+			private final Observation after;
+
+			private final AtomicReference<Observation> currentObservation = new AtomicReference<>(null);
+
+			SimpleAroundWebFilterObservation(Observation before, Observation after) {
+				this.before = before;
+				this.after = after;
+				this.observations = Arrays.asList(before, after).iterator();
+			}
+
+			@Override
+			public void start() {
+				if (this.observations.hasNext()) {
+					stop();
+					Observation observation = this.observations.next();
+					observation.start();
+					this.currentObservation.set(observation);
+				}
+			}
+
+			@Override
+			public void error(Throwable ex) {
+				Observation observation = this.currentObservation.get();
+				if (observation == null) {
+					return;
+				}
+				observation.error(ex);
+			}
+
+			@Override
+			public void stop() {
+				Observation observation = this.currentObservation.getAndSet(null);
+				if (observation == null) {
+					return;
+				}
+				observation.stop();
+			}
+
+			@Override
+			public WebFilterChain wrap(WebFilterChain chain) {
+				return (exchange) -> {
+					stop();
+					// @formatter:off
+					return chain.filter(exchange)
+							.doOnSuccess((v) -> start())
+							.doOnCancel(this::start)
+							.doOnError((t) -> {
+								error(t);
+								start();
+							});
+					// @formatter:on
+				};
+			}
+
+			@Override
+			public WebFilter wrap(WebFilter filter) {
+				return (exchange, chain) -> {
+					start();
+					// @formatter:off
+					return filter.filter(exchange, chain)
+							.doOnSuccess((v) -> stop())
+							.doOnCancel(this::stop)
+							.doOnError((t) -> {
+								error(t);
+								stop();
+							});
+					// @formatter:on
+				};
+			}
+
+			@Override
+			public Observation before() {
+				return this.before;
+			}
+
+			@Override
+			public Observation after() {
+				return this.after;
+			}
+
+		}
+
+	}
+
+	interface WebFilterObservation {
+
+		WebFilterObservation NOOP = new WebFilterObservation() {
+		};
+
+		static WebFilterObservation create(Observation observation) {
+			if (observation.isNoop()) {
+				return NOOP;
+			}
+			return new SimpleWebFilterObservation(observation);
+		}
+
+		default void start() {
+		}
+
+		default void error(Throwable ex) {
+		}
+
+		default void stop() {
+		}
+
+		default WebFilter wrap(WebFilter filter) {
+			return filter;
+		}
+
+		default WebFilterChain wrap(WebFilterChain chain) {
+			return chain;
+		}
+
+		class SimpleWebFilterObservation implements WebFilterObservation {
+
+			private final Observation observation;
+
+			SimpleWebFilterObservation(Observation observation) {
+				this.observation = observation;
+			}
+
+			@Override
+			public void start() {
+				this.observation.start();
+			}
+
+			@Override
+			public void error(Throwable ex) {
+				this.observation.error(ex);
+			}
+
+			@Override
+			public void stop() {
+				this.observation.stop();
+			}
+
+			@Override
+			public WebFilter wrap(WebFilter filter) {
+				if (this.observation.isNoop()) {
+					return filter;
+				}
+				return (exchange, chain) -> {
+					this.observation.start();
+					return filter.filter(exchange, chain).doOnSuccess((v) -> this.observation.stop())
+							.doOnCancel(this.observation::stop).doOnError((t) -> {
+								this.observation.error(t);
+								this.observation.stop();
+							});
+				};
+			}
+
+			@Override
+			public WebFilterChain wrap(WebFilterChain chain) {
+				if (this.observation.isNoop()) {
+					return chain;
+				}
+				return (exchange) -> {
+					this.observation.start();
+					return chain.filter(exchange).doOnSuccess((v) -> this.observation.stop())
+							.doOnCancel(this.observation::stop).doOnError((t) -> {
+								this.observation.error(t);
+								this.observation.stop();
+							});
+				};
+			}
+
+		}
+
+	}
+
+	static final class WebFilterChainObservationContext extends Observation.Context {
+
+		private final ServerWebExchange exchange;
+
+		private final String filterSection;
+
+		private String filterName;
+
+		private int chainPosition;
+
+		private int chainSize;
+
+		private WebFilterChainObservationContext(ServerWebExchange exchange, String filterSection) {
+			this.exchange = exchange;
+			this.filterSection = filterSection;
+		}
+
+		static WebFilterChainObservationContext before(ServerWebExchange exchange) {
+			return new WebFilterChainObservationContext(exchange, "before");
+		}
+
+		static WebFilterChainObservationContext after(ServerWebExchange exchange) {
+			return new WebFilterChainObservationContext(exchange, "after");
+		}
+
+		@Override
+		public void setName(String name) {
+			super.setName(name);
+			if (name != null) {
+				setContextualName(name + "." + this.filterSection);
+			}
+		}
+
+		String getRequestLine() {
+			return this.exchange.getRequest().getPath().toString();
+		}
+
+		String getFilterSection() {
+			return this.filterSection;
+		}
+
+		String getFilterName() {
+			return this.filterName;
+		}
+
+		void setFilterName(String filterName) {
+			this.filterName = filterName;
+		}
+
+		int getChainPosition() {
+			return this.chainPosition;
+		}
+
+		void setChainPosition(int chainPosition) {
+			this.chainPosition = chainPosition;
+		}
+
+		int getChainSize() {
+			return this.chainSize;
+		}
+
+		void setChainSize(int chainSize) {
+			this.chainSize = chainSize;
+		}
+
+	}
+
+	static final class WebFilterChainObservationConvention
+			implements ObservationConvention<WebFilterChainObservationContext> {
+
+		static final String CHAIN_OBSERVATION_NAME = "spring.security.http.chains";
+
+		private static final String REQUEST_LINE_NAME = "request.line";
+
+		private static final String CHAIN_POSITION_NAME = "chain.position";
+
+		private static final String CHAIN_SIZE_NAME = "chain.size";
+
+		private static final String FILTER_SECTION_NAME = "filter.section";
+
+		private static final String FILTER_NAME = "current.filter.name";
+
+		@Override
+		public String getName() {
+			return CHAIN_OBSERVATION_NAME;
+		}
+
+		@Override
+		public KeyValues getLowCardinalityKeyValues(WebFilterChainObservationContext context) {
+			KeyValues kv = KeyValues.of(CHAIN_SIZE_NAME, String.valueOf(context.getChainSize()))
+					.and(CHAIN_POSITION_NAME, String.valueOf(context.getChainPosition()))
+					.and(FILTER_SECTION_NAME, context.getFilterSection());
+			if (context.getFilterName() != null) {
+				kv = kv.and(FILTER_NAME, context.getFilterName());
+			}
+			return kv;
+		}
+
+		@Override
+		public KeyValues getHighCardinalityKeyValues(WebFilterChainObservationContext context) {
+			String requestLine = context.getRequestLine();
+			return KeyValues.of(REQUEST_LINE_NAME, requestLine);
+		}
+
+		@Override
+		public boolean supportsContext(Observation.Context context) {
+			return context instanceof WebFilterChainObservationContext;
+		}
+
+	}
+
+}

web/src/main/java/org/springframework/security/web/server/WebFilterChainProxy.java

@@ -1,5 +1,5 @@
 /*
- * Copyright 2002-2021 the original author or authors.
+ * Copyright 2002-2022 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.
@@ -17,11 +17,15 @@
 package org.springframework.security.web.server;
 
 import java.util.Arrays;
+import java.util.Collections;
 import java.util.List;
 
+import jakarta.servlet.FilterChain;
 import reactor.core.publisher.Flux;
 import reactor.core.publisher.Mono;
 
+import org.springframework.security.web.SecurityFilterChain;
+import org.springframework.util.Assert;
 import org.springframework.web.server.ServerWebExchange;
 import org.springframework.web.server.WebFilter;
 import org.springframework.web.server.WebFilterChain;
@@ -37,6 +41,8 @@ public class WebFilterChainProxy implements WebFilter {
 
 	private final List<SecurityWebFilterChain> filters;
 
+	private WebFilterChainDecorator filterChainDecorator = new DefaultWebFilterChainDecorator();
+
 	public WebFilterChainProxy(List<SecurityWebFilterChain> filters) {
 		this.filters = filters;
 	}
@@ -49,10 +55,82 @@ public class WebFilterChainProxy implements WebFilter {
 	public Mono<Void> filter(ServerWebExchange exchange, WebFilterChain chain) {
 		return Flux.fromIterable(this.filters)
 				.filterWhen((securityWebFilterChain) -> securityWebFilterChain.matches(exchange)).next()
-				.switchIfEmpty(chain.filter(exchange).then(Mono.empty()))
+				.switchIfEmpty(
+						Mono.defer(() -> this.filterChainDecorator.decorate(chain).filter(exchange).then(Mono.empty())))
 				.flatMap((securityWebFilterChain) -> securityWebFilterChain.getWebFilters().collectList())
-				.map((filters) -> new DefaultWebFilterChain(chain::filter, filters))
+				.map((filters) -> this.filterChainDecorator.decorate(chain, filters))
 				.flatMap((securedChain) -> securedChain.filter(exchange));
 	}
 
+	/**
+	 * Used to decorate the original {@link FilterChain} for each request
+	 *
+	 * <p>
+	 * By default, this decorates the filter chain with a {@link DefaultWebFilterChain}
+	 * that iterates through security filters and then delegates to the original chain
+	 * @param filterChainDecorator the strategy for constructing the filter chain
+	 * @since 6.0
+	 */
+	public void setFilterChainDecorator(WebFilterChainDecorator filterChainDecorator) {
+		Assert.notNull(filterChainDecorator, "filterChainDecorator cannot be null");
+		this.filterChainDecorator = filterChainDecorator;
+	}
+
+	/**
+	 * A strategy for decorating the provided filter chain with one that accounts for the
+	 * {@link SecurityFilterChain} for a given request.
+	 *
+	 * @author Josh Cummings
+	 * @since 6.0
+	 */
+	public interface WebFilterChainDecorator {
+
+		/**
+		 * Provide a new {@link FilterChain} that accounts for needed security
+		 * considerations when there are no security filters.
+		 * @param original the original {@link FilterChain}
+		 * @return a security-enabled {@link FilterChain}
+		 */
+		default WebFilterChain decorate(WebFilterChain original) {
+			return decorate(original, Collections.emptyList());
+		}
+
+		/**
+		 * Provide a new {@link FilterChain} that accounts for the provided filters as
+		 * well as teh original filter chain.
+		 * @param original the original {@link FilterChain}
+		 * @param filters the security filters
+		 * @return a security-enabled {@link FilterChain} that includes the provided
+		 * filters
+		 */
+		WebFilterChain decorate(WebFilterChain original, List<WebFilter> filters);
+
+	}
+
+	/**
+	 * A {@link WebFilterChainDecorator} that uses the {@link DefaultWebFilterChain}
+	 *
+	 * @author Josh Cummings
+	 * @since 6.0
+	 */
+	public static class DefaultWebFilterChainDecorator implements WebFilterChainDecorator {
+
+		/**
+		 * {@inheritDoc}
+		 */
+		@Override
+		public WebFilterChain decorate(WebFilterChain original) {
+			return original;
+		}
+
+		/**
+		 * {@inheritDoc}
+		 */
+		@Override
+		public WebFilterChain decorate(WebFilterChain original, List<WebFilter> filters) {
+			return new DefaultWebFilterChain(original::filter, filters);
+		}
+
+	}
+
 }

web/src/test/java/org/springframework/security/web/FilterChainProxyTests.java

@@ -16,19 +16,27 @@
 
 package org.springframework.security.web;
 
+import java.io.IOException;
 import java.util.Arrays;
 import java.util.Collections;
+import java.util.Iterator;
 import java.util.List;
 
+import io.micrometer.observation.Observation;
+import io.micrometer.observation.ObservationHandler;
+import io.micrometer.observation.ObservationRegistry;
 import jakarta.servlet.Filter;
 import jakarta.servlet.FilterChain;
 import jakarta.servlet.ServletException;
+import jakarta.servlet.ServletRequest;
+import jakarta.servlet.ServletResponse;
 import jakarta.servlet.http.HttpServletRequest;
 import jakarta.servlet.http.HttpServletRequestWrapper;
 import jakarta.servlet.http.HttpServletResponse;
 import org.junit.jupiter.api.AfterEach;
 import org.junit.jupiter.api.BeforeEach;
 import org.junit.jupiter.api.Test;
+import org.mockito.ArgumentCaptor;
 import org.mockito.stubbing.Answer;
 
 import org.springframework.mock.web.MockHttpServletRequest;
@@ -50,7 +58,9 @@ import static org.mockito.ArgumentMatchers.eq;
 import static org.mockito.BDDMockito.given;
 import static org.mockito.BDDMockito.willAnswer;
 import static org.mockito.BDDMockito.willThrow;
+import static org.mockito.Mockito.atLeastOnce;
 import static org.mockito.Mockito.mock;
+import static org.mockito.Mockito.times;
 import static org.mockito.Mockito.verify;
 import static org.mockito.Mockito.verifyNoMoreInteractions;
 
@@ -270,10 +280,198 @@ public class FilterChainProxyTests {
 		this.fcp.setRequestRejectedHandler(rjh);
 		RequestRejectedException requestRejectedException = new RequestRejectedException("Contains illegal chars");
 		ServletException servletException = new ServletException(requestRejectedException);
-		given(fw.getFirewalledRequest(this.request)).willReturn(mock(FirewalledRequest.class));
+		given(fw.getFirewalledRequest(this.request)).willReturn(new MockFirewalledRequest(this.request));
 		willThrow(servletException).given(this.chain).doFilter(any(), any());
 		this.fcp.doFilter(this.request, this.response, this.chain);
 		verify(rjh).handle(eq(this.request), eq(this.response), eq((requestRejectedException)));
 	}
 
+	@Test
+	public void doFilterWhenMatchesThenObservationRegistryObserves() throws Exception {
+		ObservationHandler<Observation.Context> handler = mock(ObservationHandler.class);
+		given(handler.supportsContext(any())).willReturn(true);
+		ObservationRegistry registry = ObservationRegistry.create();
+		registry.observationConfig().observationHandler(handler);
+		given(this.matcher.matches(any())).willReturn(true);
+		SecurityFilterChain sec = new DefaultSecurityFilterChain(this.matcher, Arrays.asList(this.filter));
+		FilterChainProxy fcp = new FilterChainProxy(sec);
+		fcp.setFilterChainDecorator(new ObservationFilterChainDecorator(registry));
+		Filter filter = ObservationFilterChainDecorator.FilterObservation
+				.create(Observation.createNotStarted("wrap", registry)).wrap(fcp);
+		filter.doFilter(this.request, this.response, this.chain);
+		ArgumentCaptor<Observation.Context> captor = ArgumentCaptor.forClass(Observation.Context.class);
+		verify(handler, times(4)).onStart(captor.capture());
+		verify(handler, times(4)).onStop(any());
+		Iterator<Observation.Context> contexts = captor.getAllValues().iterator();
+		assertThat(contexts.next().getName()).isEqualTo("wrap");
+		assertFilterChainObservation(contexts.next(), "before", 1);
+		assertThat(contexts.next().getName()).isEqualTo(ObservationFilterChainDecorator.SECURED_OBSERVATION_NAME);
+		assertFilterChainObservation(contexts.next(), "after", 1);
+	}
+
+	@Test
+	public void doFilterWhenMultipleFiltersThenObservationRegistryObserves() throws Exception {
+		ObservationHandler<Observation.Context> handler = mock(ObservationHandler.class);
+		given(handler.supportsContext(any())).willReturn(true);
+		ObservationRegistry registry = ObservationRegistry.create();
+		registry.observationConfig().observationHandler(handler);
+		given(this.matcher.matches(any())).willReturn(true);
+		Filter one = mockFilter();
+		Filter two = mockFilter();
+		Filter three = mockFilter();
+		SecurityFilterChain sec = new DefaultSecurityFilterChain(this.matcher, one, two, three);
+		FilterChainProxy fcp = new FilterChainProxy(sec);
+		fcp.setFilterChainDecorator(new ObservationFilterChainDecorator(registry));
+		Filter filter = ObservationFilterChainDecorator.FilterObservation
+				.create(Observation.createNotStarted("wrap", registry)).wrap(fcp);
+		filter.doFilter(this.request, this.response, this.chain);
+		ArgumentCaptor<Observation.Context> captor = ArgumentCaptor.forClass(Observation.Context.class);
+		verify(handler, times(4)).onStart(captor.capture());
+		verify(handler, times(4)).onStop(any());
+		Iterator<Observation.Context> contexts = captor.getAllValues().iterator();
+		assertThat(contexts.next().getName()).isEqualTo("wrap");
+		assertFilterChainObservation(contexts.next(), "before", 3);
+		assertThat(contexts.next().getName()).isEqualTo(ObservationFilterChainDecorator.SECURED_OBSERVATION_NAME);
+		assertFilterChainObservation(contexts.next(), "after", 3);
+	}
+
+	@Test
+	public void doFilterWhenMismatchesThenObservationRegistryObserves() throws Exception {
+		ObservationHandler<Observation.Context> handler = mock(ObservationHandler.class);
+		given(handler.supportsContext(any())).willReturn(true);
+		ObservationRegistry registry = ObservationRegistry.create();
+		registry.observationConfig().observationHandler(handler);
+		SecurityFilterChain sec = new DefaultSecurityFilterChain(this.matcher, Arrays.asList(this.filter));
+		FilterChainProxy fcp = new FilterChainProxy(sec);
+		fcp.setFilterChainDecorator(new ObservationFilterChainDecorator(registry));
+		Filter filter = ObservationFilterChainDecorator.FilterObservation
+				.create(Observation.createNotStarted("wrap", registry)).wrap(fcp);
+		filter.doFilter(this.request, this.response, this.chain);
+		ArgumentCaptor<Observation.Context> captor = ArgumentCaptor.forClass(Observation.Context.class);
+		verify(handler, times(2)).onStart(captor.capture());
+		verify(handler, times(2)).onStop(any());
+		Iterator<Observation.Context> contexts = captor.getAllValues().iterator();
+		assertThat(contexts.next().getName()).isEqualTo("wrap");
+		assertThat(contexts.next().getName()).isEqualTo(ObservationFilterChainDecorator.UNSECURED_OBSERVATION_NAME);
+	}
+
+	@Test
+	public void doFilterWhenFilterExceptionThenObservationRegistryObserves() throws Exception {
+		ObservationHandler<Observation.Context> handler = mock(ObservationHandler.class);
+		given(handler.supportsContext(any())).willReturn(true);
+		ObservationRegistry registry = ObservationRegistry.create();
+		registry.observationConfig().observationHandler(handler);
+		willThrow(IllegalStateException.class).given(this.filter).doFilter(any(), any(), any());
+		given(this.matcher.matches(any())).willReturn(true);
+		SecurityFilterChain sec = new DefaultSecurityFilterChain(this.matcher, Arrays.asList(this.filter));
+		FilterChainProxy fcp = new FilterChainProxy(sec);
+		fcp.setFilterChainDecorator(new ObservationFilterChainDecorator(registry));
+		Filter filter = ObservationFilterChainDecorator.FilterObservation
+				.create(Observation.createNotStarted("wrap", registry)).wrap(fcp);
+		assertThatExceptionOfType(IllegalStateException.class)
+				.isThrownBy(() -> filter.doFilter(this.request, this.response, this.chain));
+		ArgumentCaptor<Observation.Context> captor = ArgumentCaptor.forClass(Observation.Context.class);
+		verify(handler, times(2)).onStart(captor.capture());
+		verify(handler, times(2)).onStop(any());
+		verify(handler, atLeastOnce()).onError(any());
+		Iterator<Observation.Context> contexts = captor.getAllValues().iterator();
+		assertThat(contexts.next().getName()).isEqualTo("wrap");
+		assertFilterChainObservation(contexts.next(), "before", 1);
+	}
+
+	@Test
+	public void doFilterWhenExceptionWithMultipleFiltersThenObservationRegistryObserves() throws Exception {
+		ObservationHandler<Observation.Context> handler = mock(ObservationHandler.class);
+		given(handler.supportsContext(any())).willReturn(true);
+		ObservationRegistry registry = ObservationRegistry.create();
+		registry.observationConfig().observationHandler(handler);
+		given(this.matcher.matches(any())).willReturn(true);
+		Filter one = mockFilter();
+		Filter two = mock(Filter.class);
+		willThrow(IllegalStateException.class).given(two).doFilter(any(), any(), any());
+		Filter three = mockFilter();
+		SecurityFilterChain sec = new DefaultSecurityFilterChain(this.matcher, one, two, three);
+		FilterChainProxy fcp = new FilterChainProxy(sec);
+		fcp.setFilterChainDecorator(new ObservationFilterChainDecorator(registry));
+		Filter filter = ObservationFilterChainDecorator.FilterObservation
+				.create(Observation.createNotStarted("wrap", registry)).wrap(fcp);
+		assertThatExceptionOfType(IllegalStateException.class)
+				.isThrownBy(() -> filter.doFilter(this.request, this.response, this.chain));
+		ArgumentCaptor<Observation.Context> captor = ArgumentCaptor.forClass(Observation.Context.class);
+		verify(handler, times(2)).onStart(captor.capture());
+		verify(handler, times(2)).onStop(any());
+		Iterator<Observation.Context> contexts = captor.getAllValues().iterator();
+		assertThat(contexts.next().getName()).isEqualTo("wrap");
+		assertFilterChainObservation(contexts.next(), "before", 2);
+	}
+
+	@Test
+	public void doFilterWhenOneFilterDoesNotProceedThenObservationRegistryObserves() throws Exception {
+		ObservationHandler<Observation.Context> handler = mock(ObservationHandler.class);
+		given(handler.supportsContext(any())).willReturn(true);
+		ObservationRegistry registry = ObservationRegistry.create();
+		registry.observationConfig().observationHandler(handler);
+		given(this.matcher.matches(any())).willReturn(true);
+		Filter one = mockFilter();
+		Filter two = mock(Filter.class);
+		Filter three = mockFilter();
+		SecurityFilterChain sec = new DefaultSecurityFilterChain(this.matcher, one, two, three);
+		FilterChainProxy fcp = new FilterChainProxy(sec);
+		fcp.setFilterChainDecorator(new ObservationFilterChainDecorator(registry));
+		Filter filter = ObservationFilterChainDecorator.FilterObservation
+				.create(Observation.createNotStarted("wrap", registry)).wrap(fcp);
+		filter.doFilter(this.request, this.response, this.chain);
+		ArgumentCaptor<Observation.Context> captor = ArgumentCaptor.forClass(Observation.Context.class);
+		verify(handler, times(3)).onStart(captor.capture());
+		verify(handler, times(3)).onStop(any());
+		Iterator<Observation.Context> contexts = captor.getAllValues().iterator();
+		assertThat(contexts.next().getName()).isEqualTo("wrap");
+		assertFilterChainObservation(contexts.next(), "before", 2);
+		assertFilterChainObservation(contexts.next(), "after", 3);
+	}
+
+	static void assertFilterChainObservation(Observation.Context context, String filterSection, int chainPosition) {
+		assertThat(context).isInstanceOf(ObservationFilterChainDecorator.FilterChainObservationContext.class);
+		ObservationFilterChainDecorator.FilterChainObservationContext filterChainObservationContext = (ObservationFilterChainDecorator.FilterChainObservationContext) context;
+		assertThat(context.getName())
+				.isEqualTo(ObservationFilterChainDecorator.FilterChainObservationConvention.CHAIN_OBSERVATION_NAME);
+		assertThat(context.getContextualName()).endsWith(filterSection);
+		assertThat(filterChainObservationContext.getChainPosition()).isEqualTo(chainPosition);
+	}
+
+	static Filter mockFilter() throws Exception {
+		Filter filter = mock(Filter.class);
+		willAnswer((invocation) -> {
+			HttpServletRequest request = invocation.getArgument(0, HttpServletRequest.class);
+			HttpServletResponse response = invocation.getArgument(1, HttpServletResponse.class);
+			FilterChain chain = invocation.getArgument(2, FilterChain.class);
+			chain.doFilter(request, response);
+			return null;
+		}).given(filter).doFilter(any(), any(), any());
+		return filter;
+	}
+
+	private static class MockFirewalledRequest extends FirewalledRequest {
+
+		MockFirewalledRequest(HttpServletRequest request) {
+			super(request);
+		}
+
+		@Override
+		public void reset() {
+
+		}
+
+	}
+
+	private static class MockFilter implements Filter {
+
+		@Override
+		public void doFilter(ServletRequest request, ServletResponse response, FilterChain chain)
+				throws IOException, ServletException {
+			chain.doFilter(request, response);
+		}
+
+	}
+
 }

web/src/test/java/org/springframework/security/web/server/WebFilterChainProxyTests.java

@@ -17,12 +17,22 @@
 package org.springframework.security.web.server;
 
 import java.util.Arrays;
+import java.util.Iterator;
 import java.util.List;
 
+import io.micrometer.observation.Observation;
+import io.micrometer.observation.ObservationHandler;
+import io.micrometer.observation.ObservationRegistry;
 import org.junit.jupiter.api.Test;
+import org.mockito.ArgumentCaptor;
 import reactor.core.publisher.Mono;
 
 import org.springframework.http.HttpStatus;
+import org.springframework.mock.http.server.reactive.MockServerHttpRequest;
+import org.springframework.mock.web.server.MockServerWebExchange;
+import org.springframework.security.web.server.ObservationWebFilterChainDecorator.WebFilterChainObservationContext;
+import org.springframework.security.web.server.ObservationWebFilterChainDecorator.WebFilterChainObservationConvention;
+import org.springframework.security.web.server.ObservationWebFilterChainDecorator.WebFilterObservation;
 import org.springframework.security.web.server.util.matcher.ServerWebExchangeMatcher;
 import org.springframework.security.web.server.util.matcher.ServerWebExchangeMatcher.MatchResult;
 import org.springframework.test.web.reactive.server.WebTestClient;
@@ -30,6 +40,15 @@ import org.springframework.web.server.ServerWebExchange;
 import org.springframework.web.server.WebFilter;
 import org.springframework.web.server.WebFilterChain;
 
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.Assertions.assertThatExceptionOfType;
+import static org.mockito.ArgumentMatchers.any;
+import static org.mockito.BDDMockito.given;
+import static org.mockito.Mockito.atLeastOnce;
+import static org.mockito.Mockito.mock;
+import static org.mockito.Mockito.times;
+import static org.mockito.Mockito.verify;
+
 /**
  * @author Rob Winch
  * @since 5.0
@@ -47,6 +66,86 @@ public class WebFilterChainProxyTests {
 				.isNotFound();
 	}
 
+	@Test
+	public void doFilterWhenMatchesThenObservationRegistryObserves() {
+		ObservationHandler<Observation.Context> handler = mock(ObservationHandler.class);
+		given(handler.supportsContext(any())).willReturn(true);
+		ObservationRegistry registry = ObservationRegistry.create();
+		registry.observationConfig().observationHandler(handler);
+		List<WebFilter> filters = Arrays.asList(new PassthroughWebFilter());
+		ServerWebExchangeMatcher match = (exchange) -> MatchResult.match();
+		MatcherSecurityWebFilterChain chain = new MatcherSecurityWebFilterChain(match, filters);
+		WebFilterChainProxy fcp = new WebFilterChainProxy(chain);
+		fcp.setFilterChainDecorator(new ObservationWebFilterChainDecorator(registry));
+		WebFilter filter = WebFilterObservation.create(Observation.createNotStarted("wrap", registry)).wrap(fcp);
+		WebFilterChain mockChain = mock(WebFilterChain.class);
+		given(mockChain.filter(any())).willReturn(Mono.empty());
+		filter.filter(MockServerWebExchange.from(MockServerHttpRequest.get("/")), mockChain).block();
+		ArgumentCaptor<Observation.Context> captor = ArgumentCaptor.forClass(Observation.Context.class);
+		verify(handler, times(4)).onStart(captor.capture());
+		Iterator<Observation.Context> contexts = captor.getAllValues().iterator();
+		assertThat(contexts.next().getName()).isEqualTo("wrap");
+		assertFilterChainObservation(contexts.next(), "before", 1);
+		assertThat(contexts.next().getName()).isEqualTo(ObservationWebFilterChainDecorator.SECURED_OBSERVATION_NAME);
+		assertFilterChainObservation(contexts.next(), "after", 1);
+	}
+
+	@Test
+	public void doFilterWhenMismatchesThenObservationRegistryObserves() {
+		ObservationHandler<Observation.Context> handler = mock(ObservationHandler.class);
+		given(handler.supportsContext(any())).willReturn(true);
+		ObservationRegistry registry = ObservationRegistry.create();
+		registry.observationConfig().observationHandler(handler);
+		List<WebFilter> filters = Arrays.asList(new PassthroughWebFilter());
+		ServerWebExchangeMatcher notMatch = (exchange) -> MatchResult.notMatch();
+		MatcherSecurityWebFilterChain chain = new MatcherSecurityWebFilterChain(notMatch, filters);
+		WebFilterChainProxy fcp = new WebFilterChainProxy(chain);
+		fcp.setFilterChainDecorator(new ObservationWebFilterChainDecorator(registry));
+		WebFilter filter = WebFilterObservation.create(Observation.createNotStarted("wrap", registry)).wrap(fcp);
+		WebFilterChain mockChain = mock(WebFilterChain.class);
+		given(mockChain.filter(any())).willReturn(Mono.empty());
+		filter.filter(MockServerWebExchange.from(MockServerHttpRequest.get("/")), mockChain).block();
+		ArgumentCaptor<Observation.Context> captor = ArgumentCaptor.forClass(Observation.Context.class);
+		verify(handler, times(2)).onStart(captor.capture());
+		Iterator<Observation.Context> contexts = captor.getAllValues().iterator();
+		assertThat(contexts.next().getName()).isEqualTo("wrap");
+		assertThat(contexts.next().getName()).isEqualTo(ObservationWebFilterChainDecorator.UNSECURED_OBSERVATION_NAME);
+	}
+
+	@Test
+	public void doFilterWhenFilterExceptionThenObservationRegistryObserves() {
+		ObservationHandler<Observation.Context> handler = mock(ObservationHandler.class);
+		given(handler.supportsContext(any())).willReturn(true);
+		ObservationRegistry registry = ObservationRegistry.create();
+		registry.observationConfig().observationHandler(handler);
+		WebFilter error = mock(WebFilter.class);
+		given(error.filter(any(), any())).willReturn(Mono.error(new IllegalStateException()));
+		List<WebFilter> filters = Arrays.asList(error);
+		ServerWebExchangeMatcher match = (exchange) -> MatchResult.match();
+		MatcherSecurityWebFilterChain chain = new MatcherSecurityWebFilterChain(match, filters);
+		WebFilterChainProxy fcp = new WebFilterChainProxy(chain);
+		fcp.setFilterChainDecorator(new ObservationWebFilterChainDecorator(registry));
+		WebFilter filter = WebFilterObservation.create(Observation.createNotStarted("wrap", registry)).wrap(fcp);
+		WebFilterChain mockChain = mock(WebFilterChain.class);
+		given(mockChain.filter(any())).willReturn(Mono.empty());
+		assertThatExceptionOfType(IllegalStateException.class).isThrownBy(
+				() -> filter.filter(MockServerWebExchange.from(MockServerHttpRequest.get("/")), mockChain).block());
+		ArgumentCaptor<Observation.Context> captor = ArgumentCaptor.forClass(Observation.Context.class);
+		verify(handler, times(2)).onStart(captor.capture());
+		verify(handler, atLeastOnce()).onError(any());
+		Iterator<Observation.Context> contexts = captor.getAllValues().iterator();
+		assertThat(contexts.next().getName()).isEqualTo("wrap");
+		assertFilterChainObservation(contexts.next(), "before", 1);
+	}
+
+	static void assertFilterChainObservation(Observation.Context context, String filterSection, int chainPosition) {
+		assertThat(context).isInstanceOf(WebFilterChainObservationContext.class);
+		WebFilterChainObservationContext filterChainObservationContext = (WebFilterChainObservationContext) context;
+		assertThat(context.getName()).isEqualTo(WebFilterChainObservationConvention.CHAIN_OBSERVATION_NAME);
+		assertThat(context.getContextualName()).endsWith(filterSection);
+		assertThat(filterChainObservationContext.getChainPosition()).isEqualTo(chainPosition);
+	}
+
 	static class Http200WebFilter implements WebFilter {
 
 		@Override
@@ -56,4 +155,13 @@ public class WebFilterChainProxyTests {
 
 	}
 
+	static class PassthroughWebFilter implements WebFilter {
+
+		@Override
+		public Mono<Void> filter(ServerWebExchange exchange, WebFilterChain chain) {
+			return chain.filter(exchange);
+		}
+
+	}
+
 }