diff --git a/spring-cloud-contract-spec/src/main/groovy/org/springframework/cloud/contract/spec/internal/OptionalProperty.groovy b/spring-cloud-contract-spec/src/main/groovy/org/springframework/cloud/contract/spec/internal/OptionalProperty.groovy
index d9a524eccd..7efc7e9963 100644
--- a/spring-cloud-contract-spec/src/main/groovy/org/springframework/cloud/contract/spec/internal/OptionalProperty.groovy
+++ b/spring-cloud-contract-spec/src/main/groovy/org/springframework/cloud/contract/spec/internal/OptionalProperty.groovy
@@ -16,7 +16,10 @@
 
 package org.springframework.cloud.contract.spec.internal
 
+import java.util.regex.Pattern
+
 import groovy.transform.CompileStatic
+import groovy.transform.PackageScope
 import groovy.transform.ToString
 
 /**
@@ -41,6 +44,10 @@ class OptionalProperty implements Serializable {
 		return "($value)?"
 	}
 
+	protected Pattern optionalPatternValue() {
+		return Pattern.compile(optionalPattern())
+	}
+
 	@Override
 	String toString() {
 		return optionalPattern()
diff --git a/spring-cloud-contract-spec/src/main/groovy/org/springframework/cloud/contract/spec/internal/OutputMessage.groovy b/spring-cloud-contract-spec/src/main/groovy/org/springframework/cloud/contract/spec/internal/OutputMessage.groovy
index d7c7a861c0..c64f14f3ff 100644
--- a/spring-cloud-contract-spec/src/main/groovy/org/springframework/cloud/contract/spec/internal/OutputMessage.groovy
+++ b/spring-cloud-contract-spec/src/main/groovy/org/springframework/cloud/contract/spec/internal/OutputMessage.groovy
@@ -88,16 +88,26 @@ class OutputMessage extends Common {
 		this.assertThat = new ExecutionProperty(assertThat)
 	}
 
-	DslProperty value(ServerDslProperty server) {
-		Object value = server.clientValue
-		if (server.clientValue instanceof Pattern) {
-			value = StringEscapeUtils.escapeJava(new Xeger(((Pattern)server.clientValue).pattern()).generate())
+	DslProperty value(ClientDslProperty clientDslProperty) {
+		Object clientValue = clientDslProperty.clientValue
+		// for the output messages ran via stub runner,
+		// entries have to have fixed values
+		if (clientDslProperty.clientValue instanceof Pattern) {
+			clientValue = StringEscapeUtils.escapeJava(new Xeger(((Pattern)clientDslProperty.clientValue).pattern()).generate())
 		}
-		return new DslProperty(value, server.serverValue)
+		return new DslProperty(clientValue, clientDslProperty.clientValue)
 	}
 
-	DslProperty $(ServerDslProperty server) {
-		return value(server)
+	DslProperty $(ClientDslProperty client) {
+		return value(client)
+	}
+
+	DslProperty $(Pattern pattern) {
+		return value(client(pattern))
+	}
+
+	DslProperty $(OptionalProperty property) {
+		return value(client(property.optionalPatternValue()))
 	}
 
 	void testMatchers(@DelegatesTo(ResponseBodyMatchers) Closure closure) {
diff --git a/spring-cloud-contract-stub-runner/src/test/groovy/org/springframework/cloud/contract/stubrunner/StubRunnerExecutorSpec.groovy b/spring-cloud-contract-stub-runner/src/test/groovy/org/springframework/cloud/contract/stubrunner/StubRunnerExecutorSpec.groovy
index fdcfbf5f29..54f6c48e4f 100644
--- a/spring-cloud-contract-stub-runner/src/test/groovy/org/springframework/cloud/contract/stubrunner/StubRunnerExecutorSpec.groovy
+++ b/spring-cloud-contract-stub-runner/src/test/groovy/org/springframework/cloud/contract/stubrunner/StubRunnerExecutorSpec.groovy
@@ -147,6 +147,27 @@ class StubRunnerExecutorSpec extends Specification {
 			executor.shutdown()
 	}
 
+	def 'should generate regex values when message is to be set and it contains regex'() {
+		given:
+			MessageVerifier messageVerifier = Mock(MessageVerifier)
+			StubRunnerExecutor executor = new StubRunnerExecutor(portScanner, messageVerifier, [])
+		when:
+			def stubConf = new StubConfiguration('asd', 'asd', 'asd', '')
+			executor.runStubs(stubRunnerOptions,
+					new StubRepository(new File('src/test/resources/messages'),
+							[], new StubRunnerOptionsBuilder().build()), stubConf)
+			boolean triggered = executor.trigger("trigger")
+		then:
+			triggered
+			1 * messageVerifier.send({ it ->
+				!it.toString().contains("cursor")
+			}, { Map map ->
+				!map.values().any { it.toString().contains("cursor")}
+			}, _)
+		cleanup:
+			executor.shutdown()
+	}
+
 	Map<StubConfiguration, Integer> stubIdsWithPortsFromString(String stubIdsToPortMapping) {
 		return stubIdsToPortMapping.split(',').collectEntries { String entry ->
 			return StubsParser.fromStringWithPort(entry)
diff --git a/spring-cloud-contract-stub-runner/src/test/resources/messages/message.groovy b/spring-cloud-contract-stub-runner/src/test/resources/messages/message.groovy
new file mode 100644
index 0000000000..0e815b518f
--- /dev/null
+++ b/spring-cloud-contract-stub-runner/src/test/resources/messages/message.groovy
@@ -0,0 +1,27 @@
+org.springframework.cloud.contract.spec.Contract.make {
+	description 'issue #650'
+	label 'trigger'
+	input {
+		triggeredBy('createNewPerson()')
+	}
+	outputMessage {
+		sentTo 'personEventsTopic'
+		headers {
+			[
+					header('contentType': 'application/json'),
+					header('type': 'person'),
+					header('eventType': 'PersonChangedEvent'),
+					header('customerId': $(producer(regex(uuid()))))
+			]
+		}
+		body([
+				"type"      : 'CREATED',
+				"personId"  : $(producer(regex(uuid())), consumer('0fd552ba-8043-42da-ab97-4fc77e1057c9')),
+				"userId"    : $(producer(optional(regex(uuid()))), consumer('f043ccf1-0b72-423b-ad32-4ef123718897')),
+				"firstName" : $(regex(nonEmpty())),
+				"middleName": $(optional(regex(nonEmpty()))),
+				"lastName"  : $(regex(nonEmpty())),
+				"version"   : $(producer(regex(number())), consumer(0l))
+		])
+	}
+}
\ No newline at end of file