diff --git a/specs/spring-cloud-contract-spec-java/src/main/java/org/springframework/cloud/contract/spec/internal/OptionalProperty.java b/specs/spring-cloud-contract-spec-java/src/main/java/org/springframework/cloud/contract/spec/internal/OptionalProperty.java
index 7d7d51b5d0..b4f9065184 100644
--- a/specs/spring-cloud-contract-spec-java/src/main/java/org/springframework/cloud/contract/spec/internal/OptionalProperty.java
+++ b/specs/spring-cloud-contract-spec-java/src/main/java/org/springframework/cloud/contract/spec/internal/OptionalProperty.java
@@ -54,6 +54,9 @@ public class OptionalProperty implements Serializable, CanBeDynamic {
 		else if (value instanceof ClientDslProperty) {
 			return valueToCheck(((ClientDslProperty) value).getClientValue());
 		}
+		else if (value instanceof ServerDslProperty) {
+			return valueToCheck(((ServerDslProperty) value).getServerValue());
+		}
 		else if (value instanceof RegexProperty || value instanceof Pattern) {
 			return new RegexProperty(value).pattern();
 		}
diff --git a/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/ContentUtils.groovy b/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/ContentUtils.groovy
index 9a95c501a3..3c94859745 100644
--- a/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/ContentUtils.groovy
+++ b/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/ContentUtils.groovy
@@ -322,7 +322,7 @@ class ContentUtils {
 	}
 
 	protected static Object transformJSONStringValue(OptionalProperty optional, Closure valueProvider) {
-		return String.format(JSON_VALUE_PATTERN_FOR_OPTIONAL, optional.value)
+		return String.format(JSON_VALUE_PATTERN_FOR_OPTIONAL, optional.value())
 	}
 
 	protected static Object transformJSONStringValue(ExecutionProperty property, Closure valueProvider) {
diff --git a/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/builder/MethodBodyBuilderSpec.groovy b/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/builder/MethodBodyBuilderSpec.groovy
index 0526672946..438ac76587 100644
--- a/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/builder/MethodBodyBuilderSpec.groovy
+++ b/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/builder/MethodBodyBuilderSpec.groovy
@@ -2174,4 +2174,68 @@ response:
 			}
 	}
 
+	@Issue("1808")
+	def "should correctly process optional of DslProperty parameters"() {
+		given:
+			Contract contractDsl = Contract.make {
+				request {
+					method('GET')
+					url("/api/foo")
+					headers {
+						header 'Content-Type': 'application/json'
+						header 'Accept': 'application/json'
+					}
+					body([
+							key1: $(client(optional(anyOf("foo", "bar"))), server("bar")),
+							key2: $(client(optional(anyNonBlankString())), server("bar")),
+							key3: $(client(optional(anyEmail())), server("foo@bar.com")),
+							key4: $(optional(anyNumber()))
+					])
+				}
+				response {
+					status OK()
+					headers {
+						header 'Content-Type': 'application/json'
+					}
+					body([
+							key1: $(client("bar"), server(optional(anyOf("foo", "bar")))),
+							key2: $(client("bar"), server(optional(anyNonBlankString()))),
+							key3: $(client("foo@bar.com"), server(optional(anyEmail()))),
+							key4: $(optional(anyNumber()))
+					])
+				}
+			}
+			methodBuilder()
+		when:
+			String test = singleTestGenerator(contractDsl)
+		then:
+			SyntaxChecker.tryToCompile(methodBuilderName, test)
+		then:
+			test.contains('assertThatJson(parsedJson).field("[\'key1\']").matches("(^foo' + endOfLineRegexSymbol + '|^bar' + endOfLineRegexSymbol + ')?")')
+			test.contains('assertThatJson(parsedJson).field("[\'key2\']").matches("(^\\\\s*\\\\S[\\\\S\\\\s]*)?")')
+			test.contains('assertThatJson(parsedJson).field("[\'key3\']").matches("([a-zA-Z0-9._%+-]+@[a-zA-Z0-9.-]+\\\\.[a-zA-Z]{2,6})?")')
+			test.contains('assertThatJson(parsedJson).field("[\'key4\']").matches("(-?(\\\\d*\\\\.\\\\d+|\\\\d+))?")')
+		and:
+			stubMappingIsValidWireMockStub(contractDsl)
+		where:
+			methodBuilderName | methodBuilder | endOfLineRegexSymbol
+			"spock"           | {
+				properties.testFramework = TestFramework.SPOCK
+			}                                 | '\\$'
+			"mockmvc"         | {
+				properties.testMode = TestMode.MOCKMVC
+			}                                 | '\$'
+			"jaxrs-spock"     | {
+				properties.testFramework = TestFramework.SPOCK; properties.testMode = TestMode.JAXRSCLIENT
+			}                                 | '\\$'
+			"jaxrs"           | {
+				properties.testFramework = TestFramework.JUNIT; properties.testMode = TestMode.JAXRSCLIENT
+			}                                 | '\$'
+			"webclient"       | {
+				properties.testMode = TestMode.WEBTESTCLIENT
+			}                                 | '\$'
+			"testNG"          | {
+				properties.testFramework = TestFramework.TESTNG
+			}                                 | '\$'
+	}
 }
diff --git a/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/dsl/wiremock/WireMockGroovyDslSpec.groovy b/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/dsl/wiremock/WireMockGroovyDslSpec.groovy
index 53e6e4aa73..e700b83c01 100755
--- a/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/dsl/wiremock/WireMockGroovyDslSpec.groovy
+++ b/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/dsl/wiremock/WireMockGroovyDslSpec.groovy
@@ -3130,6 +3130,74 @@ class WireMockGroovyDslSpec extends Specification implements WireMockStubVerifie
 			stubMappingIsValidWireMockStub(wireMockStub)
 	}
 
+	@Issue("1808")
+	def "should correctly process optional of DslProperty parameters"() {
+		given:
+			org.springframework.cloud.contract.spec.Contract groovyDsl = org.springframework.cloud.contract.spec.Contract.
+					make {
+						request {
+							method('GET')
+							url("/api/foo")
+							headers {
+								header("Content-Type", "application/json")
+								header("Accept", "application/json")
+							}
+							body(
+								key1: $(client(optional(anyOf("foo", "bar"))), server("bar")),
+								key2: $(client(optional(anyNonBlankString())), server("bar")),
+								key3: $(client(optional(anyEmail())), server("foo@bar.com")),
+								key4: $(optional(anyNumber())),
+							)
+						}
+						response {
+							status OK()
+							body("ok")
+							headers {
+								header 'Content-Type': 'text/plain'
+							}
+						}
+					}
+		when:
+			String wireMockStub = new WireMockStubStrategy("Test", new ContractMetadata(null, false, 0, null, groovyDsl), groovyDsl).
+					toWireMockClientStub()
+		then:
+			AssertionUtil.assertThatJsonsAreEqual('''
+			{
+			  "request" : {
+				"url" : "/api/foo",
+				"method" : "GET",
+				"headers" : {
+					"Content-Type" : {
+						"equalTo" : "application/json"
+					},
+					"Accept" : {
+						"equalTo" : "application/json"
+					}
+				},
+				"bodyPatterns" : [ {
+					"matchesJsonPath" : "$[?(@.['key1'] =~ /(^foo$|^bar$)?/)]"
+				}, {
+					"matchesJsonPath" : "$[?(@.['key2'] =~ /(^\\\\s*\\\\S[\\\\S\\\\s]*)?/)]"
+				}, {
+					"matchesJsonPath" : "$[?(@.['key3'] =~ /([a-zA-Z0-9._%+-]+@[a-zA-Z0-9.-]+\\\\.[a-zA-Z]{2,6})?/)]"
+				}, {
+					"matchesJsonPath" : "$[?(@.['key4'] =~ /(-?(\\\\d*\\\\.\\\\d+|\\\\d+))?/)]"
+				} ]
+			  },
+			  "response" : {
+				"status" : 200,
+				"body" : "ok",
+				"headers" : {
+				  "Content-Type" : "text/plain"
+				},
+				"transformers" : [ "response-template", "foo-transformer" ]
+			  }
+			}
+			''', wireMockStub)
+		and:
+			stubMappingIsValidWireMockStub(wireMockStub)
+	}
+
 	WireMockConfiguration config() {
 		return new WireMockConfiguration().extensions(responseTemplateTransformer())
 	}