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In most cases you should be able to just upgrade the dependency. When you say it doesn’t work, what do you mean specifically?

In my case the wiremock is integrated with cucumber and the mocks will start and shutdown for each use case, when. and my code is

@CucumberContextConfiguration
@ContextConfiguration
@RunWith(Cucumber.class)
@CucumberOptions(
    plugin = {
      "pretty",
      "json:./build/reports/cucumber-reports/acceptance-test-results.json",
      "html:./build/reports/cucumber-reports/acceptance-test-results.html"
    },
    features = {"classpath:features"},
    extraGlue = "com.stepdefs")

// Spring server configuration
@AutoConfigureWebTestClient
@ActiveProfiles("actest")
@SpringBootTest(
    classes = NavigationApiApplication.class,
    webEnvironment = SpringBootTest.WebEnvironment.RANDOM_PORT)

// Wiremock config
// port = 0 sets a dynamic port:
// <https://cloud.spring.io/spring-cloud-contract/2.0.x/multi/multi__spring_cloud_contract_wiremock.html>
@AutoConfigureWireMock(
    port = 0,
    stubs = "file:src/test/resources/wiremock/mappings",
    files = "file:src/test/resources/wiremock")
public class LocalCucumberRunner {}

the above code uses dependencies like

// Cucumber
testImplementation 'io.cucumber:cucumber-java:7.15.0'
testImplementation 'io.cucumber:cucumber-junit:7.15.0'
testImplementation 'io.cucumber:cucumber-spring:7.15.0'
testImplementation 'io.cucumber:cucumber-junit-platform-engine:7.15.0'
testImplementation group: 'io.cucumber', name: 'cucumber-html', version: '0.2.7'

// Wiremock
testImplementation 'com.github.tomakehurst:wiremock-jre8-standalone:2.35.1'
testImplementation("org.springframework.cloud:spring-cloud-contract-wiremock:4.0.3") {
    exclude module: 'wiremock-jre8-standalone'
}

You’ve got an old version of spring-cloud-contract-wiremock and you’ve still got the jre8 dependency in there

I tried with this combination

testImplementation 'org.wiremock:wiremock-standalone:3.3.1'
testImplementation("org.springframework.cloud:spring-cloud-contract-wiremock:4.1.0") {
    exclude module: 'wiremock-jre8-standalone'
}

The combination of dependencies you’ve shown should work as far as I know, but there are a lot of moving parts here so unfortunately I think it’s a case of digging into the specific errors being thrown and addressing them.

Suppressed: java.lang.IllegalStateException: ApplicationContext failure threshold (1) exceeded: skipping repeated attempt to load context for [WebMergedContextConfiguration@4c2ad035 testClass = com.discover.enterprise.web.nav.local.LocalCucumberRunner, locations = [], classes = [com.nav.SpringBootApplication], contextInitializerClasses = [], activeProfiles = ["actest"], propertySourceDescriptors = [], propertySourceProperties = ["org.springframework.boot.test.context.SpringBootTestContextBootstrapper=true", "server.port=0"], contextCustomizers = [org.springframework.boot.test.autoconfigure.actuate.observability.ObservabilityContextCustomizerFactory$DisableObservabilityContextCustomizer@1f, org.springframework.boot.test.autoconfigure.properties.PropertyMappingContextCustomizer@56b9402e, org.springframework.boot.test.autoconfigure.web.servlet.WebDriverContextCustomizer@28a0fd6c, [ImportsContextCustomizer@4b7ab262 key = [org.springframework.boot.autoconfigure.security.reactive.ReactiveSecurityAutoConfiguration, org.springframework.cloud.contract.wiremock.WireMockRestTemplateConfiguration, org.springframework.boot.autoconfigure.security.reactive.ReactiveUserDetailsServiceAutoConfiguration, org.springframework.cloud.contract.wiremock.WireMockConfiguration, org.springframework.boot.autoconfigure.security.oauth2.client.reactive.ReactiveOAuth2ClientAutoConfiguration, org.springframework.boot.autoconfigure.security.oauth2.resource.reactive.ReactiveOAuth2ResourceServerAutoConfiguration, org.springframework.boot.test.autoconfigure.web.reactive.WebTestClientAutoConfiguration]], org.springframework.boot.test.context.filter.ExcludeFilterContextCustomizer@549621f3, org.springframework.boot.test.json.DuplicateJsonObjectContextCustomizerFactory$DuplicateJsonObjectContextCustomizer@293bb8a5, org.springframework.boot.test.mock.mockito.MockitoContextCustomizer@0, org.springframework.boot.test.web.client.TestRestTemplateContextCustomizer@5cc69cfe, org.springframework.boot.test.context.SpringBootTestAnnotation@30fe89e9], resourceBasePath = "src/main/webapp", contextLoader = org.springframework.boot.test.context.SpringBootContextLoader, parent = null]

at org.springframework.test.context.cache.DefaultCacheAwareContextLoaderDelegate.loadContext(DefaultCacheAwareContextLoaderDelegate.java:145) at org.springframework.test.context.support.DefaultTestContext.getApplicationContext(DefaultTestContext.java:130) at io.cucumber.spring.TestContextAdaptor.create(TestContextAdaptor.java:42) at io.cucumber.spring.SpringFactory.start(SpringFactory.java:121) at io.cucumber.core.runner.Runner.buildBackendWorlds(Runner.java:134) at io.cucumber.core.runner.Runner.runPickle(Runner.java:70) at io.cucumber.core.runtime.Runtime.lambda$executePickle$6(Runtime.java:107) at io.cucumber.core.runtime.CucumberExecutionContext.lambda$runTestCase$5(CucumberExecutionContext.java:137) at io.cucumber.core.runtime.RethrowingThrowableCollector.executeAndThrow(RethrowingThrowableCollector.java:23) at io.cucumber.core.runtime.CucumberExecutionContext.runTestCase(CucumberExecutionContext.java:137) at io.cucumber.core.runtime.Runtime.lambda$executePickle$7(Runtime.java:107) at java.base/java.util.concurrent.Executors$RunnableAdapter.call(Executors.java:539) at java.base/java.util.concurrent.FutureTask.run(FutureTask.java:264) at io.cucumber.core.runtime.Runtime$SameThreadExecutorService.execute(Runtime.java:235) at java.base/java.util.concurrent.AbstractExecutorService.submit(AbstractExecutorService.java:123) at io.cucumber.core.runtime.Runtime.lambda$runFeatures$3(Runtime.java:89) at java.base/java.util.stream.ReferencePipeline$3$1.accept(ReferencePipeline.java:197) at java.base/java.util.stream.SliceOps$1$1.accept(SliceOps.java:200) at java.base/java.util.ArrayList$ArrayListSpliterator.tryAdvance(ArrayList.java:1602) at java.base/java.util.stream.ReferencePipeline.forEachWithCancel(ReferencePipeline.java:129) at java.base/java.util.stream.AbstractPipeline.copyIntoWithCancel(AbstractPipeline.java:527) at java.base/java.util.stream.AbstractPipeline.copyInto(AbstractPipeline.java:513) at java.base/java.util.stream.AbstractPipeline.wrapAndCopyInto(AbstractPipeline.java:499) at java.base/java.util.stream.ReduceOps$ReduceOp.evaluateSequential(ReduceOps.java:921) at java.base/java.util.stream.AbstractPipeline.evaluate(AbstractPipeline.java:234) at java.base/java.util.stream.ReferencePipeline.collect(ReferencePipeline.java:682) at io.cucumber.core.runtime.Runtime.runFeatures(Runtime.java:90) at io.cucumber.core.runtime.Runtime.lambda$run$0(Runtime.java:78) at io.cucumber.core.runtime.CucumberExecutionContext.lambda$runFeatures$6(CucumberExecutionContext.java:148) at io.cucumber.core.runtime.CucumberExecutionContext.execute(CucumberExecutionContext.java:163) at io.cucumber.core.runtime.CucumberExecutionContext.runFeatures(CucumberExecutionContext.java:146)

Looks like you have a custom test runner in there so I think you’ll need to take a closer look at what that’s doing

I already pasted the code for custom runner

@CucumberContextConfiguration
@ContextConfiguration
@RunWith(Cucumber.class)
@CucumberOptions(
    plugin = {
      "pretty",
      "json:./build/reports/cucumber-reports/acceptance-test-results.json",
      "html:./build/reports/cucumber-reports/acceptance-test-results.html"
    },
    features = {"classpath:features"},
    extraGlue = "com.stepdefs")

// Spring server configuration
@AutoConfigureWebTestClient
@ActiveProfiles("actest")
@SpringBootTest(
    classes = SpringBootApplication.class,
    webEnvironment = SpringBootTest.WebEnvironment.RANDOM_PORT)

// Wiremock config
// port = 0 sets a dynamic port:
// <https://cloud.spring.io/spring-cloud-contract/2.0.x/multi/multi__spring_cloud_contract_wiremock.html>
@AutoConfigureWireMock(
    port = 0,
    stubs = "file:src/test/resources/wiremock/mappings",
    files = "file:src/test/resources/wiremock")
public class LocalCucumberRunner {}

Yes, but I can’t run your tests and set breakpoints to see what actual error is being thrown internally