diff --git a/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/JsonToJsonPathsConverter.groovy b/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/JsonToJsonPathsConverter.groovy
index 1d1c4c49ad..1935c7835b 100644
--- a/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/JsonToJsonPathsConverter.groovy
+++ b/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/JsonToJsonPathsConverter.groovy
@@ -50,6 +50,7 @@ class JsonToJsonPathsConverter {
 
 	private static final Boolean SERVER_SIDE = false
 	private static final Boolean CLIENT_SIDE = true
+	private static final String ANY_ARRAY_NOTATION_IN_JSONPATH = "[*]"
 
 	private final ContractVerifierConfigProperties configProperties
 
@@ -80,6 +81,7 @@ class JsonToJsonPathsConverter {
 			bodyMatchers.jsonPathMatchers().each { BodyMatcher matcher ->
 				try {
 					context.delete(matcher.path())
+					removeTrailingContainers(matcher, context)
 				} catch (RuntimeException e) {
 					if (log.isDebugEnabled()) {
 						log.debug("Exception occurred while trying to delete path [${matcher.path()}]", e)
@@ -90,6 +92,36 @@ class JsonToJsonPathsConverter {
 		return jsonCopy
 	}
 
+	/**
+	 * Related to #391. The converted body looks different when done via the String notation than
+	 * it does when done via a map notation. When working with String body and when matchers
+	 * are provided, even when all entries of a map / list got removed, the map / list itself
+	 * remains. That leads to unnecessary creation of checks for empty collection. With this method
+	 * we're checking if the JSON path matcher is related to array checking and we're trying to
+	 * remove that trailing collection. All in all it's better to use the Groovy based notation for
+	 * defining body...
+	 */
+	private static void removeTrailingContainers(BodyMatcher matcher, DocumentContext context) {
+		if (matcher.path().contains(ANY_ARRAY_NOTATION_IN_JSONPATH)) {
+			String pathWithoutAnyArray = matcher.path().substring(0, matcher.path().lastIndexOf(ANY_ARRAY_NOTATION_IN_JSONPATH))
+			def object = context.read(pathWithoutAnyArray)
+			if (object instanceof Iterable && containsOnlyEmptyElements(object)) {
+				context.delete(pathWithoutAnyArray)
+			}
+		}
+	}
+
+	private static boolean containsOnlyEmptyElements(Object object) {
+		return object.every {
+			if (it instanceof Map) {
+				return it.isEmpty()
+			} else if (it instanceof List) {
+				return it.isEmpty()
+			}
+			return false
+		}
+	}
+
 	// Doing a clone doesn't work for nested lists...
 	private static Object cloneBody(Object object) {
 		if (object instanceof List) {
diff --git a/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/builder/MockMvcMethodBodyBuilderWithMatchersSpec.groovy b/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/builder/MockMvcMethodBodyBuilderWithMatchersSpec.groovy
index 96da05eaa6..61a256a99f 100644
--- a/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/builder/MockMvcMethodBodyBuilderWithMatchersSpec.groovy
+++ b/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/builder/MockMvcMethodBodyBuilderWithMatchersSpec.groovy
@@ -423,4 +423,94 @@ class MockMvcMethodBodyBuilderWithMatchersSpec extends Specification implements
 			"JaxRsClientJUnitMethodBodyBuilder"                  | { Contract dsl -> new JaxRsClientJUnitMethodBodyBuilder(dsl, properties) }                  | '$'
 	}
 
+	@Issue("#391")
+	def "should work for matchers and body with multiline string for [#methodBuilderName]"() {
+		given:
+			Contract contractDsl = Contract.make {
+				request {
+					name "ISSUE 391"
+					method 'GET'
+					urlPath '/item/factsheet?size=2&page=1'
+					headers { header "accept", "application/...json" }
+				}
+				response {
+					status 200
+					body("""
+							{
+								"items": [
+									{
+										"id": "35309",
+										"title": "lorem ipsum"
+									}
+								]
+							}
+						""")
+					testMatchers {
+						jsonPath('$.items[*].id', byRegex(nonBlank()))
+						jsonPath('$.items[*].title', byRegex(nonBlank()))
+						jsonPath('$.items[*]', byType { minOccurrence(2); maxOccurrence(2) })
+					}
+					headers {header "content-type", "application/...json;charset=UTF-8"}
+				}
+			}
+			MethodBodyBuilder builder = methodBuilder(contractDsl)
+			BlockBuilder blockBuilder = new BlockBuilder(" ")
+		and:
+			builder.appendTo(blockBuilder)
+			String test = blockBuilder.toString()
+		when:
+			SyntaxChecker.tryToCompile(methodBuilderName, test)
+		then:
+			!test.contains('''assertThatJson(parsedJson).array("['items']").isEmpty()''')
+		where:
+			methodBuilderName                                    | methodBuilder
+			"MockMvcSpockMethodBuilder"                          | { Contract dsl -> new MockMvcSpockMethodRequestProcessingBodyBuilder(dsl, properties) }
+			"MockMvcJUnitMethodBuilder"                          | { Contract dsl -> new MockMvcJUnitMethodBodyBuilder(dsl, properties) }
+			"JaxRsClientSpockMethodRequestProcessingBodyBuilder" | { Contract dsl -> new JaxRsClientSpockMethodRequestProcessingBodyBuilder(dsl, properties) }
+			"JaxRsClientJUnitMethodBodyBuilder"                  | { Contract dsl -> new JaxRsClientJUnitMethodBodyBuilder(dsl, properties) }
+	}
+
+	@Issue("#391")
+	def "should work for matchers and body with multiline string with map body for [#methodBuilderName]"() {
+		given:
+			Contract contractDsl = Contract.make {
+				request {
+					name "ISSUE 391"
+					method 'GET'
+					urlPath '/item/factsheet?size=2&page=1'
+					headers { header "accept", "application/...json" }
+				}
+				response {
+					status 200
+					body([
+							"items": [
+									"id"   : "35309",
+									"title": "lorem ipsum"
+							]
+					])
+					testMatchers {
+						jsonPath('$.items[*].id', byRegex(nonBlank()))
+						jsonPath('$.items[*].title', byRegex(nonBlank()))
+						jsonPath('$.items[*]', byType { minOccurrence(2); maxOccurrence(2) })
+					}
+					headers {header "content-type", "application/...json;charset=UTF-8"}
+				}
+			}
+			MethodBodyBuilder builder = methodBuilder(contractDsl)
+			BlockBuilder blockBuilder = new BlockBuilder(" ")
+		and:
+			builder.appendTo(blockBuilder)
+			String test = blockBuilder.toString()
+		when:
+			SyntaxChecker.tryToCompile(methodBuilderName, test)
+		then:
+			!test.contains('''assertThatJson(parsedJson).array("['items']").isEmpty()''')
+		where:
+			methodBuilderName                                    | methodBuilder
+			"MockMvcSpockMethodBuilder"                          | { Contract dsl -> new MockMvcSpockMethodRequestProcessingBodyBuilder(dsl, properties) }
+			"MockMvcJUnitMethodBuilder"                          | { Contract dsl -> new MockMvcJUnitMethodBodyBuilder(dsl, properties) }
+			"JaxRsClientSpockMethodRequestProcessingBodyBuilder" | { Contract dsl -> new JaxRsClientSpockMethodRequestProcessingBodyBuilder(dsl, properties) }
+			"JaxRsClientJUnitMethodBodyBuilder"                  | { Contract dsl -> new JaxRsClientJUnitMethodBodyBuilder(dsl, properties) }
+	}
+
 }