diff --git a/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockApplicationListener.java b/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockApplicationListener.java
index f964c6264a..047e784333 100644
--- a/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockApplicationListener.java
+++ b/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockApplicationListener.java
@@ -54,10 +54,7 @@ public class WireMockApplicationListener implements ApplicationListener<Applicat
 		Integer httpPortProperty = environment.getProperty("wiremock.server.port", Integer.class);
 		// If the httpPortProperty is not found it means the AutoConfigureWireMock hasn't
 		// been initialised.
-		if (httpPortProperty == null) {
-			return;
-		}
-		if (isHttpDynamic(httpPortProperty)) {
+		if (httpPortProperty != null && isHttpDynamic(httpPortProperty)) {
 			registerPropertySourceForDynamicEntries(environment, "wiremock.server.port", 10000, 12500,
 					"wiremock.server.port-dynamic");
 			if (log.isDebugEnabled()) {
diff --git a/spring-cloud-contract-wiremock/src/test/java/org/springframework/cloud/contract/wiremock/AutoConfigureWireMockOnlyHttpsPortApplicationTests.java b/spring-cloud-contract-wiremock/src/test/java/org/springframework/cloud/contract/wiremock/AutoConfigureWireMockOnlyHttpsPortApplicationTests.java
new file mode 100644
index 0000000000..2e26c2630f
--- /dev/null
+++ b/spring-cloud-contract-wiremock/src/test/java/org/springframework/cloud/contract/wiremock/AutoConfigureWireMockOnlyHttpsPortApplicationTests.java
@@ -0,0 +1,59 @@
+/*
+ * Copyright 2013-2020 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.cloud.contract.wiremock;
+
+import org.junit.Test;
+import org.junit.runner.RunWith;
+
+import org.springframework.beans.factory.annotation.Autowired;
+import org.springframework.boot.test.context.SpringBootTest;
+import org.springframework.boot.test.context.SpringBootTest.WebEnvironment;
+import org.springframework.test.context.junit4.SpringRunner;
+
+import static com.github.tomakehurst.wiremock.client.WireMock.aResponse;
+import static com.github.tomakehurst.wiremock.client.WireMock.get;
+import static com.github.tomakehurst.wiremock.client.WireMock.stubFor;
+import static com.github.tomakehurst.wiremock.client.WireMock.urlEqualTo;
+import static org.assertj.core.api.Assertions.assertThat;
+
+@RunWith(SpringRunner.class)
+@SpringBootTest(classes = WiremockTestsApplication.class,
+		properties = "app.baseUrl=https://localhost:${wiremock.server.https-port}",
+		webEnvironment = WebEnvironment.NONE)
+@AutoConfigureWireMock(httpsPort = 9999)
+public class AutoConfigureWireMockOnlyHttpsPortApplicationTests {
+
+	@Autowired
+	private Service service;
+
+	@Autowired
+	private WireMockProperties wireMockProperties;
+
+	@Test
+	public void contextLoads() throws Exception {
+		stubFor(get(urlEqualTo("/test"))
+				.willReturn(aResponse().withHeader("Content-Type", "text/plain").withBody("Hello World!")));
+		assertThat(this.service.go()).isEqualTo("Hello World!");
+	}
+
+	@Test
+	public void portsAreFixed() {
+		boolean httpsPortDynamic = this.wireMockProperties.getServer().isHttpsPortDynamic();
+		assertThat(httpsPortDynamic).isFalse();
+	}
+
+}
diff --git a/spring-cloud-contract-wiremock/src/test/java/org/springframework/cloud/contract/wiremock/AutoConfigureWireMockOnlyRandomPortHttpsApplicationTests.java b/spring-cloud-contract-wiremock/src/test/java/org/springframework/cloud/contract/wiremock/AutoConfigureWireMockOnlyRandomPortHttpsApplicationTests.java
new file mode 100644
index 0000000000..59bc6e52e5
--- /dev/null
+++ b/spring-cloud-contract-wiremock/src/test/java/org/springframework/cloud/contract/wiremock/AutoConfigureWireMockOnlyRandomPortHttpsApplicationTests.java
@@ -0,0 +1,59 @@
+/*
+ * Copyright 2013-2020 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.cloud.contract.wiremock;
+
+import org.junit.Test;
+import org.junit.runner.RunWith;
+
+import org.springframework.beans.factory.annotation.Autowired;
+import org.springframework.boot.test.context.SpringBootTest;
+import org.springframework.boot.test.context.SpringBootTest.WebEnvironment;
+import org.springframework.test.context.junit4.SpringRunner;
+
+import static com.github.tomakehurst.wiremock.client.WireMock.aResponse;
+import static com.github.tomakehurst.wiremock.client.WireMock.get;
+import static com.github.tomakehurst.wiremock.client.WireMock.stubFor;
+import static com.github.tomakehurst.wiremock.client.WireMock.urlEqualTo;
+import static org.assertj.core.api.Assertions.assertThat;
+
+@RunWith(SpringRunner.class)
+@SpringBootTest(classes = WiremockTestsApplication.class,
+		properties = "app.baseUrl=https://localhost:${wiremock.server.https-port}",
+		webEnvironment = WebEnvironment.NONE)
+@AutoConfigureWireMock(httpsPort = 0)
+public class AutoConfigureWireMockOnlyRandomPortHttpsApplicationTests {
+
+	@Autowired
+	private Service service;
+
+	@Autowired
+	private WireMockProperties wireMockProperties;
+
+	@Test
+	public void contextLoads() throws Exception {
+		stubFor(get(urlEqualTo("/test"))
+				.willReturn(aResponse().withHeader("Content-Type", "text/plain").withBody("Hello World!")));
+		assertThat(this.service.go()).isEqualTo("Hello World!");
+	}
+
+	@Test
+	public void portsAreNotFixed() {
+		boolean httpsPortDynamic = this.wireMockProperties.getServer().isHttpsPortDynamic();
+		assertThat(httpsPortDynamic).isTrue();
+	}
+
+}