diff --git a/spring-test/src/main/java/org/springframework/test/json/AbstractJsonValueAssert.java b/spring-test/src/main/java/org/springframework/test/json/AbstractJsonValueAssert.java
new file mode 100644
index 00000000000..f3c9181369d
--- /dev/null
+++ b/spring-test/src/main/java/org/springframework/test/json/AbstractJsonValueAssert.java
@@ -0,0 +1,235 @@
+/*
+ * Copyright 2002-2024 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.test.json;
+
+import java.lang.reflect.Array;
+import java.lang.reflect.Type;
+import java.util.List;
+import java.util.Map;
+
+import org.assertj.core.api.AbstractBooleanAssert;
+import org.assertj.core.api.AbstractMapAssert;
+import org.assertj.core.api.AbstractObjectAssert;
+import org.assertj.core.api.AbstractStringAssert;
+import org.assertj.core.api.Assertions;
+import org.assertj.core.api.ObjectArrayAssert;
+import org.assertj.core.error.BasicErrorMessageFactory;
+import org.assertj.core.internal.Failures;
+
+import org.springframework.core.ParameterizedTypeReference;
+import org.springframework.core.ResolvableType;
+import org.springframework.http.HttpInputMessage;
+import org.springframework.http.MediaType;
+import org.springframework.http.converter.GenericHttpMessageConverter;
+import org.springframework.lang.Nullable;
+import org.springframework.mock.http.MockHttpInputMessage;
+import org.springframework.mock.http.MockHttpOutputMessage;
+import org.springframework.util.ObjectUtils;
+import org.springframework.util.StringUtils;
+
+/**
+ * Base AssertJ {@link org.assertj.core.api.Assert assertions} that can be
+ * applied to a JSON value. In JSON, values must be one of the following data
+ * types:
+ * <ul>
+ * <li>a {@linkplain #asString() string}</li>
+ * <li>a {@linkplain #asNumber() number}</li>
+ * <li>a {@linkplain #asBoolean() boolean}</li>
+ * <li>an {@linkplain #asArray() array}</li>
+ * <li>an {@linkplain #asMap() object} (JSON object)</li>
+ * <li>{@linkplain #isNull() null}</li>
+ * </ul>
+ * This base class offers direct access for each of those types as well as a
+ * conversion methods based on an optional {@link GenericHttpMessageConverter}.
+ *
+ * @author Stephane Nicoll
+ * @since 6.2
+ * @param <SELF> the type of assertions
+ */
+public abstract class AbstractJsonValueAssert<SELF extends AbstractJsonValueAssert<SELF>>
+		extends AbstractObjectAssert<SELF, Object> {
+
+	private final Failures failures = Failures.instance();
+
+	@Nullable
+	private final GenericHttpMessageConverter<Object> httpMessageConverter;
+
+
+	protected AbstractJsonValueAssert(@Nullable Object actual, Class<?> selfType,
+			@Nullable GenericHttpMessageConverter<Object> httpMessageConverter) {
+		super(actual, selfType);
+		this.httpMessageConverter = httpMessageConverter;
+	}
+
+	/**
+	 * Verify that the actual value is a non-{@code null} {@link String}
+	 * and return a new {@linkplain AbstractStringAssert assertion} object that
+	 * provides dedicated {@code String} assertions for it.
+	 */
+	@Override
+	public AbstractStringAssert<?> asString() {
+		return Assertions.assertThat(castTo(String.class, "a string"));
+	}
+
+	/**
+	 * Verify that the actual value is a non-{@code null} {@link Number},
+	 * usually an {@link Integer} or {@link Double} and return a new
+	 * {@linkplain AbstractObjectAssert assertion} object for it.
+	 */
+	public AbstractObjectAssert<?, Number> asNumber() {
+		return Assertions.assertThat(castTo(Number.class, "a number"));
+	}
+
+	/**
+	 * Verify that the actual value is a non-{@code null} {@link Boolean}
+	 * and return a new {@linkplain AbstractBooleanAssert assertion} object
+	 * that provides dedicated {@code Boolean} assertions for it.
+	 */
+	public AbstractBooleanAssert<?> asBoolean() {
+		return Assertions.assertThat(castTo(Boolean.class, "a boolean"));
+	}
+
+	/**
+	 * Verify that the actual value is a non-{@code null} {@link Array}
+	 * and return a new {@linkplain ObjectArrayAssert assertion} object
+	 * that provides dedicated {@code Array} assertions for it.
+	 */
+	public ObjectArrayAssert<Object> asArray() {
+		List<?> list = castTo(List.class, "an array");
+		Object[] array = list.toArray(new Object[0]);
+		return Assertions.assertThat(array);
+	}
+
+	/**
+	 * Verify that the actual value is a non-{@code null} JSON object and
+	 * return a new {@linkplain AbstractMapAssert assertion} object that
+	 * provides dedicated assertions on individual elements of the
+	 * object. The returned map assertion object uses the attribute name as the
+	 * key, and the value can itself be any of the valid JSON values.
+	 */
+	@SuppressWarnings("unchecked")
+	public AbstractMapAssert<?, Map<String, Object>, String, Object> asMap() {
+		return Assertions.assertThat(castTo(Map.class, "a map"));
+	}
+
+	private <T> T castTo(Class<T> expectedType, String description) {
+		if (this.actual == null) {
+			throw valueProcessingFailed("To be %s%n".formatted(description));
+		}
+		if (!expectedType.isInstance(this.actual)) {
+			throw valueProcessingFailed("To be %s%nBut was:%n  %s%n".formatted(description, this.actual.getClass().getName()));
+		}
+		return expectedType.cast(this.actual);
+	}
+
+	/**
+	 * Verify that the actual value can be converted to an instance of the
+	 * given {@code target} and produce a new {@linkplain AbstractObjectAssert
+	 * assertion} object narrowed to that type.
+	 * @param target the {@linkplain Class type} to convert the actual value to
+	 */
+	public <T> AbstractObjectAssert<?, T> convertTo(Class<T> target) {
+		isNotNull();
+		T value = convertToTargetType(target);
+		return Assertions.assertThat(value);
+	}
+
+	/**
+	 * Verify that the actual value can be converted to an instance of the
+	 * given {@code target} and produce a new {@linkplain AbstractObjectAssert
+	 * assertion} object narrowed to that type.
+	 * @param target the {@linkplain ParameterizedTypeReference parameterized
+	 * type} to convert the actual value to
+	 */
+	public <T> AbstractObjectAssert<?, T> convertTo(ParameterizedTypeReference<T> target) {
+		isNotNull();
+		T value = convertToTargetType(target.getType());
+		return Assertions.assertThat(value);
+	}
+
+	/**
+	 * Verify that the actual value is empty, that is a {@code null} scalar
+	 * value or an empty list or map. Can also be used when the path is using a
+	 * filter operator to validate that it dit not match.
+	 */
+	public SELF isEmpty() {
+		if (!ObjectUtils.isEmpty(this.actual)) {
+			throw valueProcessingFailed("To be empty");
+		}
+		return this.myself;
+	}
+
+	/**
+	 * Verify that the actual value is not empty, that is a non-{@code null}
+	 * scalar value or a non-empty list or map. Can also be used when the path is
+	 * using a filter operator to validate that it dit match at least one
+	 * element.
+	 */
+	public SELF isNotEmpty() {
+		if (ObjectUtils.isEmpty(this.actual)) {
+			throw valueProcessingFailed("To not be empty");
+		}
+		return this.myself;
+	}
+
+
+	@SuppressWarnings("unchecked")
+	private <T> T convertToTargetType(Type targetType) {
+		if (this.httpMessageConverter == null) {
+			throw new IllegalStateException(
+					"No JSON message converter available to convert %s".formatted(actualToString()));
+		}
+		try {
+			MockHttpOutputMessage outputMessage = new MockHttpOutputMessage();
+			this.httpMessageConverter.write(this.actual, ResolvableType.forInstance(this.actual).getType(),
+					MediaType.APPLICATION_JSON, outputMessage);
+			return (T) this.httpMessageConverter.read(targetType, getClass(),
+					fromHttpOutputMessage(outputMessage));
+		}
+		catch (Exception ex) {
+			throw valueProcessingFailed("To convert successfully to:%n  %s%nBut it failed:%n  %s%n"
+					.formatted(targetType.getTypeName(), ex.getMessage()));
+		}
+	}
+
+	private HttpInputMessage fromHttpOutputMessage(MockHttpOutputMessage message) {
+		MockHttpInputMessage inputMessage = new MockHttpInputMessage(message.getBodyAsBytes());
+		inputMessage.getHeaders().addAll(message.getHeaders());
+		return inputMessage;
+	}
+
+	protected String getExpectedErrorMessagePrefix() {
+		return "Expected:";
+	}
+
+	private AssertionError valueProcessingFailed(String errorMessage) {
+		throw this.failures.failure(this.info, new ValueProcessingFailed(
+				getExpectedErrorMessagePrefix(), actualToString(), errorMessage));
+	}
+
+	private String actualToString() {
+		return ObjectUtils.nullSafeToString(StringUtils.quoteIfString(this.actual));
+	}
+
+	private static final class ValueProcessingFailed extends BasicErrorMessageFactory {
+
+		private ValueProcessingFailed(String prefix, String actualToString, String errorMessage) {
+			super("%n%s%n  %s%n%s".formatted(prefix, actualToString, errorMessage));
+		}
+	}
+
+}
diff --git a/spring-test/src/main/java/org/springframework/test/json/JsonPathAssert.java b/spring-test/src/main/java/org/springframework/test/json/JsonPathAssert.java
new file mode 100644
index 00000000000..0064b58140d
--- /dev/null
+++ b/spring-test/src/main/java/org/springframework/test/json/JsonPathAssert.java
@@ -0,0 +1,165 @@
+/*
+ * Copyright 2002-2024 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.test.json;
+
+import java.util.function.Consumer;
+
+import com.jayway.jsonpath.JsonPath;
+import com.jayway.jsonpath.PathNotFoundException;
+import org.assertj.core.api.AbstractAssert;
+import org.assertj.core.api.AssertProvider;
+import org.assertj.core.error.BasicErrorMessageFactory;
+import org.assertj.core.internal.Failures;
+
+import org.springframework.http.converter.GenericHttpMessageConverter;
+import org.springframework.lang.Nullable;
+import org.springframework.util.Assert;
+
+/**
+ * AssertJ {@link org.assertj.core.api.Assert assertions} that can be applied
+ * to a {@link CharSequence} representation of a json document using
+ * {@linkplain JsonPath JSON path}.
+ *
+ * @author Stephane Nicoll
+ * @since 6.2
+ */
+public class JsonPathAssert extends AbstractAssert<JsonPathAssert, CharSequence> {
+
+	private static final Failures failures = Failures.instance();
+
+	@Nullable
+	private final GenericHttpMessageConverter<Object> jsonMessageConverter;
+
+	public JsonPathAssert(CharSequence json,
+			@Nullable GenericHttpMessageConverter<Object> jsonMessageConverter) {
+		super(json, JsonPathAssert.class);
+		this.jsonMessageConverter = jsonMessageConverter;
+	}
+
+	/**
+	 * Verify that the given JSON {@code path} is present and extract the JSON
+	 * value for further {@linkplain JsonPathValueAssert assertions}.
+	 * @param path the {@link JsonPath} expression
+	 * @see #hasPathSatisfying(String, Consumer)
+	 */
+	public JsonPathValueAssert extractingPath(String path) {
+		Object value = new JsonPathValue(path).getValue();
+		return new JsonPathValueAssert(value, path, this.jsonMessageConverter);
+	}
+
+	/**
+	 * Verify that the given JSON {@code path} is present with a JSON value
+	 * satisfying the given {@code valueRequirements}.
+	 * @param path the {@link JsonPath} expression
+	 * @param valueRequirements a {@link Consumer} of the assertion object
+	 */
+	public JsonPathAssert hasPathSatisfying(String path, Consumer<AssertProvider<JsonPathValueAssert>> valueRequirements) {
+		Object value = new JsonPathValue(path).assertHasPath();
+		JsonPathValueAssert valueAssert = new JsonPathValueAssert(value, path, this.jsonMessageConverter);
+		valueRequirements.accept(() -> valueAssert);
+		return this;
+	}
+
+	/**
+	 * Verify that the given JSON {@code path} matches. For paths with an
+	 * operator, this validates that the path expression is valid, but does not
+	 * validate that it yield any results.
+	 * @param path the {@link JsonPath} expression
+	 */
+	public JsonPathAssert hasPath(String path) {
+		new JsonPathValue(path).assertHasPath();
+		return this;
+	}
+
+	/**
+	 * Verify that the given JSON {@code path} does not match.
+	 * @param path the {@link JsonPath} expression
+	 */
+	public JsonPathAssert doesNotHavePath(String path) {
+		new JsonPathValue(path).assertDoesNotHavePath();
+		return this;
+	}
+
+
+	private AssertionError failure(BasicErrorMessageFactory errorMessageFactory) {
+		throw failures.failure(this.info, errorMessageFactory);
+	}
+
+
+	/**
+	 * A {@link JsonPath} value.
+	 */
+	private class JsonPathValue {
+
+		private final String path;
+
+		private final JsonPath jsonPath;
+
+		private final String json;
+
+		JsonPathValue(String path) {
+			Assert.hasText(path, "'path' must not be null or empty");
+			this.path = path;
+			this.jsonPath = JsonPath.compile(this.path);
+			this.json = JsonPathAssert.this.actual.toString();
+		}
+
+		@Nullable
+		Object assertHasPath() {
+			return getValue();
+		}
+
+		void assertDoesNotHavePath() {
+			try {
+				read();
+				throw failure(new JsonPathNotExpected(this.json, this.path));
+			}
+			catch (PathNotFoundException ignore) {
+			}
+		}
+
+		@Nullable
+		Object getValue() {
+			try {
+				return read();
+			}
+			catch (PathNotFoundException ex) {
+				throw failure(new JsonPathNotFound(this.json, this.path));
+			}
+		}
+
+		@Nullable
+		private Object read() {
+			return this.jsonPath.read(this.json);
+		}
+
+
+		static final class JsonPathNotFound extends BasicErrorMessageFactory {
+
+			private JsonPathNotFound(String actual, String path) {
+				super("%nExpecting:%n  %s%nTo match JSON path:%n  %s%n", actual, path);
+			}
+		}
+
+		static final class JsonPathNotExpected extends BasicErrorMessageFactory {
+
+			private JsonPathNotExpected(String actual, String path) {
+				super("%nExpecting:%n  %s%nTo not match JSON path:%n  %s%n", actual, path);
+			}
+		}
+	}
+}
diff --git a/spring-test/src/main/java/org/springframework/test/json/JsonPathValueAssert.java b/spring-test/src/main/java/org/springframework/test/json/JsonPathValueAssert.java
new file mode 100644
index 00000000000..468c4ec5061
--- /dev/null
+++ b/spring-test/src/main/java/org/springframework/test/json/JsonPathValueAssert.java
@@ -0,0 +1,48 @@
+/*
+ * Copyright 2002-2024 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.test.json;
+
+import com.jayway.jsonpath.JsonPath;
+
+import org.springframework.http.converter.GenericHttpMessageConverter;
+import org.springframework.lang.Nullable;
+
+/**
+ * AssertJ {@link org.assertj.core.api.Assert assertions} that can be applied
+ * to a JSON value produced by evaluating a {@linkplain JsonPath JSON path}
+ * expression.
+ *
+ * @author Stephane Nicoll
+ * @since 6.2
+ */
+public class JsonPathValueAssert
+		extends AbstractJsonValueAssert<JsonPathValueAssert> {
+
+	private final String expression;
+
+
+	JsonPathValueAssert(@Nullable Object actual, String expression,
+			@Nullable GenericHttpMessageConverter<Object> httpMessageConverter) {
+		super(actual, JsonPathValueAssert.class, httpMessageConverter);
+		this.expression = expression;
+	}
+
+	@Override
+	protected String getExpectedErrorMessagePrefix() {
+		return "Expected value at JSON path \"%s\":".formatted(this.expression);
+	}
+}
diff --git a/spring-test/src/test/java/org/springframework/test/json/JsonPathAssertTests.java b/spring-test/src/test/java/org/springframework/test/json/JsonPathAssertTests.java
new file mode 100644
index 00000000000..b48914ec543
--- /dev/null
+++ b/spring-test/src/test/java/org/springframework/test/json/JsonPathAssertTests.java
@@ -0,0 +1,322 @@
+/*
+ * Copyright 2002-2024 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.test.json;
+
+import java.util.List;
+import java.util.Map;
+import java.util.function.Consumer;
+import java.util.stream.Stream;
+
+import com.fasterxml.jackson.databind.ObjectMapper;
+import org.assertj.core.api.AssertProvider;
+import org.junit.jupiter.api.Nested;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.params.ParameterizedTest;
+import org.junit.jupiter.params.provider.Arguments;
+import org.junit.jupiter.params.provider.MethodSource;
+import org.junit.jupiter.params.provider.ValueSource;
+
+import org.springframework.core.ParameterizedTypeReference;
+import org.springframework.core.io.ClassPathResource;
+import org.springframework.http.converter.GenericHttpMessageConverter;
+import org.springframework.http.converter.json.MappingJackson2HttpMessageConverter;
+import org.springframework.lang.Nullable;
+import org.springframework.util.FileCopyUtils;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.Assertions.assertThatExceptionOfType;
+import static org.assertj.core.api.Assertions.assertThatIllegalStateException;
+import static org.assertj.core.api.Assertions.entry;
+
+/**
+ * Tests for {@link JsonPathAssert}.
+ *
+ * @author Phillip Webb
+ * @author Stephane Nicoll
+ */
+class JsonPathAssertTests {
+
+	private static final String TYPES = loadJson("types.json");
+
+	private static final String SIMPSONS = loadJson("simpsons.json");
+
+	private static final String NULLS = loadJson("nulls.json");
+
+	private static final MappingJackson2HttpMessageConverter jsonHttpMessageConverter =
+			new MappingJackson2HttpMessageConverter(new ObjectMapper());
+
+
+	@Nested
+	class HasPathTests {
+
+		@Test
+		void hasPathForPresentAndNotNull() {
+			assertThat(forJson(NULLS)).hasPath("$.valuename");
+		}
+
+		@Test
+		void hasPathForPresentAndNull() {
+			assertThat(forJson(NULLS)).hasPath("$.nullname");
+		}
+
+		@Test
+		void hasPathForOperatorMatching() {
+			assertThat(forJson(SIMPSONS)).
+					hasPath("$.familyMembers[?(@.name == 'Homer')]");
+		}
+
+		@Test
+		void hasPathForOperatorNotMatching() {
+			assertThat(forJson(SIMPSONS)).
+					hasPath("$.familyMembers[?(@.name == 'Dilbert')]");
+		}
+
+		@Test
+		void hasPathForNotPresent() {
+			String expression = "$.missing";
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(forJson(NULLS)).hasPath(expression))
+					.satisfies(hasFailedToMatchPath("$.missing"));
+		}
+
+		@Test
+		void hasPathSatisfying() {
+			assertThat(forJson(TYPES)).hasPathSatisfying("$.str", value -> assertThat(value).isEqualTo("foo"))
+					.hasPathSatisfying("$.num", value -> assertThat(value).isEqualTo(5));
+		}
+
+		@Test
+		void hasPathSatisfyingForPathNotPresent() {
+			String expression = "missing";
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(forJson(NULLS)).hasPathSatisfying(expression, value -> {}))
+					.satisfies(hasFailedToMatchPath(expression));
+		}
+
+		@Test
+		void doesNotHavePathForMissing() {
+			assertThat(forJson(NULLS)).doesNotHavePath("$.missing");
+		}
+
+
+		@Test
+		void doesNotHavePathForPresent() {
+			String expression = "$.valuename";
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(forJson(NULLS)).doesNotHavePath(expression))
+					.satisfies(hasFailedToNotMatchPath(expression));
+		}
+	}
+
+
+	@Nested
+	class ExtractingPathTests {
+
+		@Test
+		void isNullWithNullPathValue() {
+			assertThat(forJson(NULLS)).extractingPath("$.nullname").isNull();
+		}
+
+		@ParameterizedTest
+		@ValueSource(strings = { "$.str", "$.emptyString", "$.num", "$.bool", "$.arr",
+				"$.emptyArray", "$.colorMap", "$.emptyMap" })
+		void isNotNullWithValue(String path) {
+			assertThat(forJson(TYPES)).extractingPath(path).isNotNull();
+		}
+
+		@ParameterizedTest
+		@MethodSource
+		void isEqualToOnRawValue(String path, Object expected) {
+			assertThat(forJson(TYPES)).extractingPath(path).isEqualTo(expected);
+		}
+
+		static Stream<Arguments> isEqualToOnRawValue() {
+			return Stream.of(
+					Arguments.of("$.str", "foo"),
+					Arguments.of("$.num", 5),
+					Arguments.of("$.bool", true),
+					Arguments.of("$.arr", List.of(42)),
+					Arguments.of("$.colorMap", Map.of("red", "rojo")));
+		}
+
+		@Test
+		void asStringWithActualValue() {
+			assertThat(forJson(TYPES)).extractingPath("@.str").asString().startsWith("f").endsWith("o");
+		}
+
+		@Test
+		void asStringIsEmpty() {
+			assertThat(forJson(TYPES)).extractingPath("@.emptyString").asString().isEmpty();
+		}
+
+		@Test
+		void asNumberWithActualValue() {
+			assertThat(forJson(TYPES)).extractingPath("@.num").asNumber().isEqualTo(5);
+		}
+
+		@Test
+		void asBooleanWithActualValue() {
+			assertThat(forJson(TYPES)).extractingPath("@.bool").asBoolean().isTrue();
+		}
+
+		@Test
+		void asArrayWithActualValue() {
+			assertThat(forJson(TYPES)).extractingPath("@.arr").asArray().containsOnly(42);
+		}
+
+		@Test
+		void asArrayIsEmpty() {
+			assertThat(forJson(TYPES)).extractingPath("@.emptyArray").asArray().isEmpty();
+		}
+
+		@Test
+		void asArrayWithFilterPredicatesMatching() {
+			assertThat(forJson(SIMPSONS))
+					.extractingPath("$.familyMembers[?(@.name == 'Bart')]").asArray().hasSize(1);
+		}
+
+		@Test
+		void asArrayWithFilterPredicatesNotMatching() {
+			assertThat(forJson(SIMPSONS)).
+					extractingPath("$.familyMembers[?(@.name == 'Dilbert')]").asArray().isEmpty();
+		}
+
+		@Test
+		void asMapWithActualValue() {
+			assertThat(forJson(TYPES)).extractingPath("@.colorMap").asMap().containsOnly(entry("red", "rojo"));
+		}
+
+		@Test
+		void asMapIsEmpty() {
+			assertThat(forJson(TYPES)).extractingPath("@.emptyMap").asMap().isEmpty();
+		}
+
+		@Test
+		void convertToWithoutHttpMessageConverterShouldFail() {
+			JsonPathValueAssert path = assertThat(forJson(SIMPSONS)).extractingPath("$.familyMembers[0]");
+			assertThatIllegalStateException().isThrownBy(() -> path.convertTo(Member.class))
+					.withMessage("No JSON message converter available to convert {name=Homer}");
+		}
+
+		@Test
+		void convertToTargetType() {
+			assertThat(forJson(SIMPSONS, jsonHttpMessageConverter))
+					.extractingPath("$.familyMembers[0]").convertTo(Member.class)
+					.satisfies(member -> assertThat(member.name).isEqualTo("Homer"));
+		}
+
+		@Test
+		void convertToIncompatibleTargetTypeShouldFail() {
+			JsonPathValueAssert path = assertThat(forJson(SIMPSONS, jsonHttpMessageConverter))
+					.extractingPath("$.familyMembers[0]");
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> path.convertTo(Customer.class))
+					.withMessageContainingAll("Expected value at JSON path \"$.familyMembers[0]\":",
+							Customer.class.getName(), "name");
+		}
+
+		@Test
+		void convertArrayToParameterizedType() {
+			assertThat(forJson(SIMPSONS, jsonHttpMessageConverter))
+					.extractingPath("$.familyMembers")
+					.convertTo(new ParameterizedTypeReference<List<Member>>() {})
+					.satisfies(family -> assertThat(family).hasSize(5).element(0).isEqualTo(new Member("Homer")));
+		}
+
+		@Test
+		void isEmptyWithPathHavingNullValue() {
+			assertThat(forJson(NULLS)).extractingPath("nullname").isEmpty();
+		}
+
+		@ParameterizedTest
+		@ValueSource(strings = { "$.emptyString", "$.emptyArray", "$.emptyMap" })
+		void isEmptyWithEmptyValue(String path) {
+			assertThat(forJson(TYPES)).extractingPath(path).isEmpty();
+		}
+
+		@Test
+		void isEmptyForPathWithFilterMatching() {
+			String expression = "$.familyMembers[?(@.name == 'Bart')]";
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(forJson(SIMPSONS)).extractingPath(expression).isEmpty())
+					.withMessageContainingAll("Expected value at JSON path \"" + expression + "\"",
+							"[{\"name\":\"Bart\"}]", "To be empty");
+		}
+
+		@Test
+		void isEmptyForPathWithFilterNotMatching() {
+			assertThat(forJson(SIMPSONS)).extractingPath("$.familyMembers[?(@.name == 'Dilbert')]").isEmpty();
+		}
+
+		@ParameterizedTest
+		@ValueSource(strings = { "$.str", "$.num", "$.bool", "$.arr", "$.colorMap" })
+		void isNotEmptyWithNonNullValue(String path) {
+			assertThat(forJson(TYPES)).extractingPath(path).isNotEmpty();
+		}
+
+		@Test
+		void isNotEmptyForPathWithFilterMatching() {
+			assertThat(forJson(SIMPSONS)).extractingPath("$.familyMembers[?(@.name == 'Bart')]").isNotEmpty();
+		}
+
+		@Test
+		void isNotEmptyForPathWithFilterNotMatching() {
+			String expression = "$.familyMembers[?(@.name == 'Dilbert')]";
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(forJson(SIMPSONS)).extractingPath(expression).isNotEmpty())
+					.withMessageContainingAll("Expected value at JSON path \"" + expression + "\"",
+							"To not be empty");
+		}
+
+
+		private record Member(String name) {}
+
+		private record Customer(long id, String username) {}
+
+	}
+
+	private Consumer<AssertionError> hasFailedToMatchPath(String expression) {
+		return error -> assertThat(error.getMessage()).containsSubsequence("Expecting:",
+				"To match JSON path:", "\"" + expression + "\"");
+	}
+
+	private Consumer<AssertionError> hasFailedToNotMatchPath(String expression) {
+		return error -> assertThat(error.getMessage()).containsSubsequence("Expecting:",
+				"To not match JSON path:", "\"" + expression + "\"");
+	}
+
+
+	private static String loadJson(String path) {
+		try {
+			ClassPathResource resource = new ClassPathResource(path, JsonPathAssertTests.class);
+			return new String(FileCopyUtils.copyToByteArray(resource.getInputStream()));
+		}
+		catch (Exception ex) {
+			throw new IllegalStateException(ex);
+		}
+	}
+
+	private AssertProvider<JsonPathAssert> forJson(String json) {
+		return forJson(json, null);
+	}
+
+	private AssertProvider<JsonPathAssert> forJson(String json,
+			@Nullable GenericHttpMessageConverter<Object> jsonHttpMessageConverter) {
+		return () -> new JsonPathAssert(json, jsonHttpMessageConverter);
+	}
+
+}
diff --git a/spring-test/src/test/java/org/springframework/test/json/JsonPathValueAssertTests.java b/spring-test/src/test/java/org/springframework/test/json/JsonPathValueAssertTests.java
new file mode 100644
index 00000000000..4ed5f604cac
--- /dev/null
+++ b/spring-test/src/test/java/org/springframework/test/json/JsonPathValueAssertTests.java
@@ -0,0 +1,333 @@
+/*
+ * Copyright 2002-2024 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.test.json;
+
+import java.util.Collections;
+import java.util.List;
+import java.util.Map;
+import java.util.function.Consumer;
+
+import com.fasterxml.jackson.databind.ObjectMapper;
+import org.assertj.core.api.AssertProvider;
+import org.assertj.core.api.InstanceOfAssertFactories;
+import org.assertj.core.data.Offset;
+import org.junit.jupiter.api.Nested;
+import org.junit.jupiter.api.Test;
+
+import org.springframework.core.ParameterizedTypeReference;
+import org.springframework.http.converter.json.MappingJackson2HttpMessageConverter;
+import org.springframework.lang.Nullable;
+import org.springframework.util.StringUtils;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.Assertions.assertThatExceptionOfType;
+import static org.assertj.core.api.Assertions.assertThatIllegalStateException;
+
+/**
+ * Tests for {@link JsonPathValueAssert}.
+ *
+ * @author Stephane Nicoll
+ */
+class JsonPathValueAssertTests {
+
+	@Nested
+	class AsStringTests {
+
+		@Test
+		void asStringWithStringValue() {
+			assertThat(forValue("test")).asString().isEqualTo("test");
+		}
+
+		@Test
+		void asStringWithEmptyValue() {
+			assertThat(forValue("")).asString().isEmpty();
+		}
+
+		@Test
+		void asStringWithNonStringFails() {
+			int value = 123;
+			AssertProvider<JsonPathValueAssert> actual = forValue(value);
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(actual).asString().isEqualTo("123"))
+					.satisfies(hasFailedToBeOfType(value, "a string"));
+		}
+
+		@Test
+		void asStringWithNullFails() {
+			AssertProvider<JsonPathValueAssert> actual = forValue(null);
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(actual).asString().isEqualTo("null"))
+					.satisfies(hasFailedToBeOfTypeWhenNull("a string"));
+		}
+	}
+
+	@Nested
+	class AsNumberTests {
+
+		@Test
+		void asNumberWithIntegerValue() {
+			assertThat(forValue(123)).asNumber().isEqualTo(123);
+		}
+
+		@Test
+		void asNumberWithDoubleValue() {
+			assertThat(forValue(3.1415926)).asNumber()
+					.asInstanceOf(InstanceOfAssertFactories.DOUBLE)
+					.isEqualTo(3.14, Offset.offset(0.01));
+		}
+
+		@Test
+		void asNumberWithNonNumberFails() {
+			String value = "123";
+			AssertProvider<JsonPathValueAssert> actual = forValue(value);
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(actual).asNumber().isEqualTo(123))
+					.satisfies(hasFailedToBeOfType(value, "a number"));
+		}
+
+		@Test
+		void asNumberWithNullFails() {
+			AssertProvider<JsonPathValueAssert> actual = forValue(null);
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(actual).asNumber().isEqualTo(0))
+					.satisfies(hasFailedToBeOfTypeWhenNull("a number"));
+		}
+	}
+
+	@Nested
+	class AsBooleanTests {
+
+		@Test
+		void asBooleanWithBooleanPrimitiveValue() {
+			assertThat(forValue(true)).asBoolean().isEqualTo(true);
+		}
+
+		@Test
+		void asBooleanWithBooleanWrapperValue() {
+			assertThat(forValue(Boolean.FALSE)).asBoolean().isEqualTo(false);
+		}
+
+		@Test
+		void asBooleanWithNonBooleanFails() {
+			String value = "false";
+			AssertProvider<JsonPathValueAssert> actual = forValue(value);
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(actual).asBoolean().isEqualTo(false))
+					.satisfies(hasFailedToBeOfType(value, "a boolean"));
+		}
+
+		@Test
+		void asBooleanWithNullFails() {
+			AssertProvider<JsonPathValueAssert> actual = forValue(null);
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(actual).asBoolean().isEqualTo(false))
+					.satisfies(hasFailedToBeOfTypeWhenNull("a boolean"));
+		}
+	}
+
+	@Nested
+	class AsArrayTests { // json path uses List for arrays
+
+		@Test
+		void asArrayWithStringValues() {
+			assertThat(forValue(List.of("a", "b", "c"))).asArray().contains("a", "c");
+		}
+
+		@Test
+		void asArrayWithEmptyArray() {
+			assertThat(forValue(Collections.emptyList())).asArray().isEmpty();
+		}
+
+		@Test
+		void asArrayWithNonArrayFails() {
+			String value = "test";
+			AssertProvider<JsonPathValueAssert> actual = forValue(value);
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(actual).asArray().contains("t"))
+					.satisfies(hasFailedToBeOfType(value, "an array"));
+		}
+
+		@Test
+		void asArrayWithNullFails() {
+			AssertProvider<JsonPathValueAssert> actual = forValue(null);
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(actual).asArray().isEqualTo(false))
+					.satisfies(hasFailedToBeOfTypeWhenNull("an array"));
+		}
+	}
+
+	@Nested
+	class AsMapTests {
+
+		@Test
+		void asMapWithMapValue() {
+			assertThat(forValue(Map.of("zero", 0, "one", 1))).asMap().containsKeys("zero", "one")
+					.containsValues(0, 1);
+		}
+
+		@Test
+		void asArrayWithEmptyMap() {
+			assertThat(forValue(Collections.emptyMap())).asMap().isEmpty();
+		}
+
+		@Test
+		void asMapWithNonMapFails() {
+			List<String> value = List.of("a", "b");
+			AssertProvider<JsonPathValueAssert> actual = forValue(value);
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(actual).asMap().containsKey("a"))
+					.satisfies(hasFailedToBeOfType(value, "a map"));
+		}
+
+		@Test
+		void asMapWithNullFails() {
+			AssertProvider<JsonPathValueAssert> actual = forValue(null);
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(actual).asMap().isEmpty())
+					.satisfies(hasFailedToBeOfTypeWhenNull("a map"));
+		}
+	}
+
+	@Nested
+	class ConvertToTests {
+
+		private static final MappingJackson2HttpMessageConverter jsonHttpMessageConverter =
+				new MappingJackson2HttpMessageConverter(new ObjectMapper());
+
+		@Test
+		void convertToWithoutHttpMessageConverter() {
+			AssertProvider<JsonPathValueAssert> actual = () -> new JsonPathValueAssert("123", "$.test", null);
+			assertThatIllegalStateException().isThrownBy(() -> assertThat(actual).convertTo(Integer.class))
+					.withMessage("No JSON message converter available to convert '123'");
+		}
+
+		@Test
+		void convertObjectToPojo() {
+			assertThat(forValue(Map.of("id", 1234, "name", "John", "active", true))).convertTo(User.class)
+					.satisfies(user -> {
+						assertThat(user.id).isEqualTo(1234);
+						assertThat(user.name).isEqualTo("John");
+						assertThat(user.active).isTrue();
+					});
+		}
+
+		@Test
+		void convertArrayToListOfPojo() {
+			Map<?, ?> user1 = Map.of("id", 1234, "name", "John", "active", true);
+			Map<?, ?> user2 = Map.of("id", 5678, "name", "Sarah", "active", false);
+			Map<?, ?> user3 = Map.of("id", 9012, "name", "Sophia", "active", true);
+			assertThat(forValue(List.of(user1, user2, user3)))
+					.convertTo(new ParameterizedTypeReference<List<User>>() {})
+					.satisfies(users -> assertThat(users).hasSize(3).extracting("name")
+							.containsExactly("John", "Sarah", "Sophia"));
+		}
+
+		@Test
+		void convertObjectToPojoWithMissingMandatoryField() {
+			Map<?, ?> value = Map.of("firstName", "John");
+			AssertProvider<JsonPathValueAssert> actual = forValue(value);
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(actual).convertTo(User.class))
+					.satisfies(hasFailedToConvertToType(value, User.class))
+					.withMessageContaining("firstName");
+		}
+
+
+		private AssertProvider<JsonPathValueAssert> forValue(@Nullable Object actual) {
+			return () -> new JsonPathValueAssert(actual, "$.test", jsonHttpMessageConverter);
+		}
+
+
+		private record User(long id, String name, boolean active) {}
+
+	}
+
+	@Nested
+	class EmptyNotEmptyTests {
+
+		@Test
+		void isEmptyWithEmptyString() {
+			assertThat(forValue("")).isEmpty();
+		}
+
+		@Test
+		void isEmptyWithNull() {
+			assertThat(forValue(null)).isEmpty();
+		}
+
+		@Test
+		void isEmptyWithEmptyArray() {
+			assertThat(forValue(Collections.emptyList())).isEmpty();
+		}
+
+		@Test
+		void isEmptyWithEmptyObject() {
+			assertThat(forValue(Collections.emptyMap())).isEmpty();
+		}
+
+		@Test
+		void isEmptyWithWhitespace() {
+			AssertProvider<JsonPathValueAssert> actual = forValue("    ");
+			assertThatExceptionOfType(AssertionError.class)
+					.isThrownBy(() -> assertThat(actual).isEmpty())
+					.satisfies(hasFailedEmptyCheck("    "));
+		}
+
+		@Test
+		void isNotEmptyWithString() {
+			assertThat(forValue("test")).isNotEmpty();
+		}
+
+		@Test
+		void isNotEmptyWithArray() {
+			assertThat(forValue(List.of("test"))).isNotEmpty();
+		}
+
+		@Test
+		void isNotEmptyWithObject() {
+			assertThat(forValue(Map.of("test", "value"))).isNotEmpty();
+		}
+
+		private Consumer<AssertionError> hasFailedEmptyCheck(Object actual) {
+			return error -> assertThat(error.getMessage()).containsSubsequence("Expected value at JSON path \"$.test\":",
+					"" + StringUtils.quoteIfString(actual), "To be empty");
+		}
+	}
+
+
+	private Consumer<AssertionError> hasFailedToBeOfType(Object actual, String expectedDescription) {
+		return error -> assertThat(error.getMessage()).containsSubsequence("Expected value at JSON path \"$.test\":",
+				"" + StringUtils.quoteIfString(actual), "To be " + expectedDescription, "But was:", actual.getClass().getName());
+	}
+
+	private Consumer<AssertionError> hasFailedToBeOfTypeWhenNull(String expectedDescription) {
+		return error -> assertThat(error.getMessage()).containsSubsequence("Expected value at JSON path \"$.test\":", "null",
+				"To be " + expectedDescription);
+	}
+
+	private Consumer<AssertionError> hasFailedToConvertToType(Object actual, Class<?> targetType) {
+		return error -> assertThat(error.getMessage()).containsSubsequence("Expected value at JSON path \"$.test\":",
+				"" + StringUtils.quoteIfString(actual), "To convert successfully to:", targetType.getTypeName(), "But it failed:");
+	}
+
+
+
+	private AssertProvider<JsonPathValueAssert> forValue(@Nullable Object actual) {
+		return () -> new JsonPathValueAssert(actual, "$.test", null);
+	}
+
+}