diff --git a/spring-test/src/main/java/org/springframework/test/web/client/AbstractRequestExpectationManager.java b/spring-test/src/main/java/org/springframework/test/web/client/AbstractRequestExpectationManager.java
index ac373f89fb..a70b948860 100644
--- a/spring-test/src/main/java/org/springframework/test/web/client/AbstractRequestExpectationManager.java
+++ b/spring-test/src/main/java/org/springframework/test/web/client/AbstractRequestExpectationManager.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2002-2018 the original author or authors.
+ * 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.
@@ -20,10 +20,13 @@ import java.io.IOException;
 import java.net.URI;
 import java.util.Collection;
 import java.util.Collections;
+import java.util.LinkedHashMap;
 import java.util.LinkedHashSet;
 import java.util.LinkedList;
 import java.util.List;
+import java.util.Map;
 import java.util.Set;
+import java.util.stream.Collectors;
 
 import org.springframework.http.HttpMethod;
 import org.springframework.http.client.ClientHttpRequest;
@@ -49,6 +52,8 @@ public abstract class AbstractRequestExpectationManager implements RequestExpect
 
 	private final List<ClientHttpRequest> requests = new LinkedList<>();
 
+	private final Map<ClientHttpRequest, Throwable> requestFailures = new LinkedHashMap<>();
+
 
 	/**
 	 * Return a read-only list of the expectations.
@@ -91,6 +96,10 @@ public abstract class AbstractRequestExpectationManager implements RequestExpect
 					expectation = matchRequest(request);
 				}
 			}
+			catch (Throwable ex) {
+				this.requestFailures.put(request, ex);
+				throw ex;
+			}
 			finally {
 				this.requests.add(request);
 			}
@@ -129,7 +138,8 @@ public abstract class AbstractRequestExpectationManager implements RequestExpect
 	 * @since 5.0.3
 	 */
 	protected RequestExpectation matchRequest(ClientHttpRequest request) throws IOException {
-		throw new UnsupportedOperationException("It looks like neither the deprecated \"validateRequestInternal\"" +
+		throw new UnsupportedOperationException(
+				"It looks like neither the deprecated \"validateRequestInternal\"" +
 				"nor its replacement (this method) are implemented.");
 	}
 
@@ -148,6 +158,12 @@ public abstract class AbstractRequestExpectationManager implements RequestExpect
 			String message = "Further request(s) expected leaving " + count + " unsatisfied expectation(s).\n";
 			throw new AssertionError(message + getRequestDetails());
 		}
+		if (!this.requestFailures.isEmpty()) {
+			throw new AssertionError("Some requests did not execute successfully.\n" +
+					this.requestFailures.entrySet().stream()
+							.map(entry -> "Failed request:\n" + entry.getKey() + "\n" + entry.getValue())
+							.collect(Collectors.joining("\n", "\n", "")));
+		}
 	}
 
 	/**
diff --git a/spring-test/src/main/java/org/springframework/test/web/client/MockRestServiceServer.java b/spring-test/src/main/java/org/springframework/test/web/client/MockRestServiceServer.java
index 5666e92b41..a16bdc4ef3 100644
--- a/spring-test/src/main/java/org/springframework/test/web/client/MockRestServiceServer.java
+++ b/spring-test/src/main/java/org/springframework/test/web/client/MockRestServiceServer.java
@@ -305,11 +305,15 @@ public final class MockRestServiceServer {
 		}
 
 		@Override
-		public org.springframework.http.client.AsyncClientHttpRequest createAsyncRequest(URI uri, HttpMethod httpMethod) {
+		public org.springframework.http.client.AsyncClientHttpRequest createAsyncRequest(
+				URI uri, HttpMethod httpMethod) {
+
 			return createRequestInternal(uri, httpMethod);
 		}
 
-		private org.springframework.mock.http.client.MockAsyncClientHttpRequest createRequestInternal(URI uri, HttpMethod method) {
+		private org.springframework.mock.http.client.MockAsyncClientHttpRequest createRequestInternal(
+				URI uri, HttpMethod method) {
+
 			Assert.notNull(uri, "'uri' must not be null");
 			Assert.notNull(method, "'httpMethod' must not be null");
 
diff --git a/spring-test/src/test/java/org/springframework/test/web/client/MockRestServiceServerTests.java b/spring-test/src/test/java/org/springframework/test/web/client/MockRestServiceServerTests.java
index 45462658d5..f9af4dd58c 100644
--- a/spring-test/src/test/java/org/springframework/test/web/client/MockRestServiceServerTests.java
+++ b/spring-test/src/test/java/org/springframework/test/web/client/MockRestServiceServerTests.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2002-2017 the original author or authors.
+ * 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.
@@ -23,7 +23,9 @@ import org.junit.Test;
 import org.springframework.test.web.client.MockRestServiceServer.MockRestServiceServerBuilder;
 import org.springframework.web.client.RestTemplate;
 
+import static org.assertj.core.api.Assertions.*;
 import static org.springframework.http.HttpMethod.*;
+import static org.springframework.test.web.client.ExpectedCount.*;
 import static org.springframework.test.web.client.match.MockRestRequestMatchers.*;
 import static org.springframework.test.web.client.response.MockRestResponseCreators.*;
 
@@ -132,4 +134,25 @@ public class MockRestServiceServerTests {
 		server.verify();
 	}
 
+	@Test // gh-21799
+	public void verifyShouldFailIfRequestsFailed() {
+		MockRestServiceServer server = MockRestServiceServer.bindTo(this.restTemplate).build();
+		server.expect(once(), requestTo("/remoteurl")).andRespond(withSuccess());
+
+		this.restTemplate.postForEntity("/remoteurl", null, String.class);
+		try {
+			this.restTemplate.postForEntity("/remoteurl", null, String.class);
+		}
+		catch (AssertionError error) {
+			assertThat(error.getMessage()).startsWith("No further requests expected");
+		}
+
+		try {
+			server.verify();
+			fail("Expected verify failure");
+		}
+		catch (AssertionError error) {
+			assertThat(error.getMessage()).startsWith("Some requests did not execute successfully");
+		}
+	}
 }