diff --git a/spring-test/src/main/java/org/springframework/test/util/JsonPathExpectationsHelper.java b/spring-test/src/main/java/org/springframework/test/util/JsonPathExpectationsHelper.java
index 7a9ee1faaf..af43cb787e 100644
--- a/spring-test/src/main/java/org/springframework/test/util/JsonPathExpectationsHelper.java
+++ b/spring-test/src/main/java/org/springframework/test/util/JsonPathExpectationsHelper.java
@@ -26,6 +26,7 @@ import org.hamcrest.MatcherAssert;
 
 import org.springframework.lang.Nullable;
 import org.springframework.util.Assert;
+import org.springframework.util.ClassUtils;
 import org.springframework.util.ObjectUtils;
 import org.springframework.util.StringUtils;
 
@@ -108,10 +109,18 @@ public class JsonPathExpectationsHelper {
 			}
 			actualValue = actualValueList.get(0);
 		}
-		else if (actualValue != null && expectedValue != null) {
-			if (!actualValue.getClass().equals(expectedValue.getClass())) {
+		else if (actualValue != null && expectedValue != null &&
+				!actualValue.getClass().equals(expectedValue.getClass())) {
+			try {
 				actualValue = evaluateJsonPath(content, expectedValue.getClass());
 			}
+			catch (AssertionError error) {
+				String message = String.format(
+					"At JSON path \"%s\", value <%s> of type <%s> cannot be converted to type <%s>",
+					this.expression, actualValue, ClassUtils.getDescriptiveType(actualValue),
+					ClassUtils.getDescriptiveType(expectedValue));
+				throw new AssertionError(message, error.getCause());
+			}
 		}
 		AssertionErrors.assertEquals("JSON path \"" + this.expression + "\"", expectedValue, actualValue);
 	}
@@ -298,7 +307,7 @@ public class JsonPathExpectationsHelper {
 
 	/**
 	 * Variant of {@link #evaluateJsonPath(String)} with a target type.
-	 * This can be useful for matching numbers reliably for example coercing an
+	 * <p>This can be useful for matching numbers reliably for example coercing an
 	 * integer into a double.
 	 * @param content the content to evaluate against
 	 * @return the result of the evaluation
diff --git a/spring-test/src/test/java/org/springframework/test/web/servlet/result/JsonPathResultMatchersTests.java b/spring-test/src/test/java/org/springframework/test/web/servlet/result/JsonPathResultMatchersTests.java
index 787d0a7632..3fd1bfbcce 100644
--- a/spring-test/src/test/java/org/springframework/test/web/servlet/result/JsonPathResultMatchersTests.java
+++ b/spring-test/src/test/java/org/springframework/test/web/servlet/result/JsonPathResultMatchersTests.java
@@ -64,9 +64,17 @@ public class JsonPathResultMatchersTests {
 	}
 
 	@Test
-	public void valueWithMismatch() throws Exception {
-		assertThatExceptionOfType(AssertionError.class).isThrownBy(() ->
-				new JsonPathResultMatchers("$.str").value("bogus").match(stubMvcResult));
+	public void valueWithValueMismatch() throws Exception {
+		assertThatExceptionOfType(AssertionError.class)
+			.isThrownBy(() -> new JsonPathResultMatchers("$.str").value("bogus").match(stubMvcResult))
+			.withMessage("JSON path \"$.str\" expected:<bogus> but was:<foo>");
+	}
+
+	@Test
+	public void valueWithTypeMismatch() throws Exception {
+		assertThatExceptionOfType(AssertionError.class)
+			.isThrownBy(() -> new JsonPathResultMatchers("$.str").value("bogus".getBytes()).match(stubMvcResult))
+			.withMessage("At JSON path \"$.str\", value <foo> of type <java.lang.String> cannot be converted to type <byte[]>");
 	}
 
 	@Test