diff --git a/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockConfiguration.java b/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockConfiguration.java
index ca9ed89093..52db6962f4 100644
--- a/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockConfiguration.java
+++ b/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockConfiguration.java
@@ -118,6 +118,10 @@ public class WireMockConfiguration implements SmartLifecycle {
 		}
 	}
 
+	void resetMappings() {
+		this.server.resetToDefaultMappings();
+	}
+
 	private void registerStubs() throws IOException {
 		for (String stubs : this.wireMock.getServer().getStubs()) {
 			if (StringUtils.hasText(stubs)) {
diff --git a/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockTestExecutionListener.java b/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockTestExecutionListener.java
index 164de7e4aa..65a631c9f9 100644
--- a/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockTestExecutionListener.java
+++ b/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockTestExecutionListener.java
@@ -35,6 +35,21 @@ public final class WireMockTestExecutionListener extends AbstractTestExecutionLi
 
 	private static final Log log = LogFactory.getLog(WireMockTestExecutionListener.class);
 
+	@Override
+	public void beforeTestClass(TestContext testContext) throws Exception {
+		if (applicationContextBroken(testContext)
+				|| wireMockConfigurationMissing(testContext)
+				|| annotationMissing(testContext)) {
+			return;
+		}
+		if (!portIsFixed(testContext)) {
+			if (log.isDebugEnabled()) {
+				log.debug("Re-registering default mappings");
+			}
+			wireMockConfig(testContext).init();
+		}
+	}
+
 	@Override
 	public void afterTestClass(TestContext testContext) {
 		if (applicationContextBroken(testContext)
@@ -52,6 +67,14 @@ public final class WireMockTestExecutionListener extends AbstractTestExecutionLi
 			testContext
 					.markApplicationContextDirty(DirtiesContext.HierarchyMode.EXHAUSTIVE);
 		}
+		else {
+			if (log.isDebugEnabled()) {
+				log.debug(
+						"Resetting mappings for the next test to restart them. That's necessary when"
+								+ "reusing the same context with new servers running on random ports");
+			}
+			wireMockConfig(testContext).resetMappings();
+		}
 	}
 
 	private boolean annotationMissing(TestContext testContext) {