diff --git a/specs/spring-cloud-contract-spec-java/src/main/java/org/springframework/cloud/contract/spec/internal/PatternValueDslProperty.java b/specs/spring-cloud-contract-spec-java/src/main/java/org/springframework/cloud/contract/spec/internal/PatternValueDslProperty.java
index 17341ce87b..7f102ad6c7 100644
--- a/specs/spring-cloud-contract-spec-java/src/main/java/org/springframework/cloud/contract/spec/internal/PatternValueDslProperty.java
+++ b/specs/spring-cloud-contract-spec-java/src/main/java/org/springframework/cloud/contract/spec/internal/PatternValueDslProperty.java
@@ -168,7 +168,7 @@ abstract class PatternValueDslProperty<T extends DslProperty> implements RegexCr
 
 	@Override
 	public T anyOf(String... values) {
-		return createAndValidateProperty(RegexPatterns.anyOf(values), values[0]);
+		return createAndValidateProperty(RegexPatterns.anyOf(values), values[this.random.nextInt(values.length)]);
 	}
 
 }