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  1. ,
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    Set the mail.smtp.ssl.trust system property to an smtp host, like smtp.gmail.com.

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    If you're using wiremock, configure your code to accept wiremock self-signed certificate or create a keystore and certificate that are trusted by your HTTP client and configure wiremock to use that

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Unable to establish connection to email server from provided settings. sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to
java.lang.RuntimeException: Unable to establish connection to email server from provided settings. sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target at datameer.das.plugins.mail.MailDataStoreModel.testConnect(MailDataStoreModel.java:107) at datameer.dap.sdk.entity.DataStore.validate(DataStore.java:197) at datameer.dap.conductor.webapp.commandObject.ConnectionCommand.validateConnection(ConnectionCommand.java:121) at sun.reflect.GeneratedMethodAccessor824.invoke(Unknown Source) at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) at java.lang.reflect.Method.invoke(Method.java:606) at org.springmodules.validation.bean.rule.ValidationMethodValidationRule$MethodCondition.doCheck(ValidationMethodValidationRule.java:39) at org.springmodules.validation.util.condition.AbstractCondition.check(AbstractCondition.java:36) at org.springmodules.validation.bean.BeanValidator.validateAndShortCircuitRules(BeanValidator.java:429) at org.springmodules.validation.bean.BeanValidator.applyPropertiesValidationRules(BeanValidator.java:412) at org.springmodules.validation.bean.BeanValidator.applyBeanValidation(BeanValidator.java:349) at org.springmodules.validation.bean.BeanValidator.validateObjectGraphConstraints(BeanValidator.java:181) at org.springmodules.validation.bean.BeanValidator.validate(BeanValidator.java:99) at datameer.dap.conductor.webapp.controller.data.datastore.DataStoreW2DetailsController.submitConnectionDetails(DataStoreW2DetailsController.java:128) at datameer.dap.conductor.webapp.controller.data.datastore.DataStoreW2DetailsController$$FastClassBySpringCGLIB$$d340b755.invoke(<generated>) at org.springframework.cglib.proxy.MethodProxy.invoke(MethodProxy.java:204) at org.springframework.aop.framework.CglibAopProxy$CglibMethodInvocation.invokeJoinpoint(CglibAopProxy.java:717) at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:157) at org.springframework.security.access.intercept.aopalliance.MethodSecurityInterceptor.invoke(MethodSecurityInterceptor.java:68) at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:179) at org.springframework.aop.framework.CglibAopProxy$DynamicAdvisedInterceptor.intercept(CglibAopProxy.java:653) at datameer.dap.conductor.webapp.controller.data.datastore.DataStoreW2DetailsController$$EnhancerBySpringCGLIB$$c41c4f7f.submitConnectionDetails(<generated>) at sun.reflect.GeneratedMethodAccessor823.invoke(Unknown Source) at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) at java.lang.reflect.Method.invoke(Method.java:606) at org.springframework.web.bind.annotation.support.HandlerMethodInvoker.invokeHandlerMethod(HandlerMethodInvoker.java:177) at org.springframework.web.servlet.mvc.annotation.AnnotationMethodHandlerAdapter.invokeHandlerMethod(AnnotationMethodHandlerAdapter.java:446) at org.springframework.web.servlet.mvc.annotation.AnnotationMethodHandlerAdapter.handle(AnnotationMethodHandlerAdapter.java:434) at org.springframework.web.servlet.DispatcherServlet.doDispatch(DispatcherServlet.java:959) at org.springframework.web.servlet.DispatcherServlet.doService(DispatcherServlet.java:893) at org.springframework.web.servlet.FrameworkServlet.processRequest(FrameworkServlet.java:967) at org.springframework.web.servlet.FrameworkServlet.doGet(FrameworkServlet.java:858) at javax.servlet.http.HttpServlet.service(HttpServlet.java:687) at org.springframework.web.servlet.FrameworkServlet.service(FrameworkServlet.java:843) at javax.servlet.http.HttpServlet.service(HttpServlet.java:790) at org.eclipse.jetty.servlet.ServletHolder.handle(ServletHolder.java:808) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1669) at datameer.dap.conductor.webapp.filter.MinifyJsCssFilter.doFilter(MinifyJsCssFilter.java:49) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.HeaderInjectFilter.doFilter(HeaderInjectFilter.java:24) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.CsrfFilter.doHttpFilter(CsrfFilter.java:87) at datameer.dap.conductor.webapp.filter.CsrfFilter.doFilter(CsrfFilter.java:66) at org.springframework.web.filter.DelegatingFilterProxy.invokeDelegate(DelegatingFilterProxy.java:344) at org.springframework.web.filter.DelegatingFilterProxy.doFilter(DelegatingFilterProxy.java:261) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.SessionFilter.doFilter(SessionFilter.java:53) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.RestAuthenticationOriginFilter.doFilter(RestAuthenticationOriginFilter.java:52) at org.springframework.web.filter.DelegatingFilterProxy.invokeDelegate(DelegatingFilterProxy.java:344) at org.springframework.web.filter.DelegatingFilterProxy.doFilter(DelegatingFilterProxy.java:261) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at org.eclipse.jetty.servlets.UserAgentFilter.doFilter(UserAgentFilter.java:83) at org.eclipse.jetty.servlets.GzipFilter.doFilter(GzipFilter.java:364) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.OptimisticLockRetryFilter.doFilter(OptimisticLockRetryFilter.java:31) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.PermissionDeniedExceptionFilter.doFilter(PermissionDeniedExceptionFilter.java:29) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.RequestMetaDataFilter.doFilter(RequestMetaDataFilter.java:27) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.PersistenceFilter.doFilter(Unknown Source) at org.springframework.web.filter.DelegatingFilterProxy.invokeDelegate(DelegatingFilterProxy.java:344) at org.springframework.web.filter.DelegatingFilterProxy.doFilter(DelegatingFilterProxy.java:261) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at org.springframework.security.web.FilterChainProxy$VirtualFilterChain.doFilter(FilterChainProxy.java:316) at org.springframework.security.web.access.intercept.FilterSecurityInterceptor.invoke(FilterSecurityInterceptor.java:126) at org.springframework.security.web.access.intercept.FilterSecurityInterceptor.doFilter(FilterSecurityInterceptor.java:90) at org.springframework.security.web.FilterChainProxy$VirtualFilterChain.doFilter(FilterChainProxy.java:330) at org.springframework.security.web.access.ExceptionTranslationFilter.doFilter(ExceptionTranslationFilter.java:114) at org.springframework.security.web.FilterChainProxy$VirtualFilterChain.doFilter(FilterChainProxy.java:330) at org.springframework.security.web.session.SessionManagementFilter.doFilter(SessionManagementFilter.java:122) at org.springframework.security.web.FilterChainProxy$VirtualFilterChain.doFilter(FilterChainProxy.java:330) at org.springframework.security.web.authentication.AnonymousAuthenticationFilter.doFilter(AnonymousAuthenticationFilter.java:111) at org.springframework.security.web.FilterChainProxy$VirtualFilterChain.doFilter(FilterChainProxy.java:330) at org.springframework.security.web.authentication.rememberme.RememberMeAuthenticationFilter.doFilter(RememberMeAuthenticationFilter.java:157) at org.springframework.security.web.FilterChainProxy$VirtualFilterChain.doFilter(FilterChainProxy.java:330) at org.springframework.security.web.servletapi.SecurityContextHolderAwareRequestFilter.doFilter(SecurityContextHolderAwareRequestFilter.java:169) at org.springframework.security.web.FilterChainProxy$VirtualFilterChain.doFilter(FilterChainProxy.java:330) at org.springframework.security.web.savedrequest.RequestCacheAwareFilter.doFilter(RequestCacheAwareFilter.java:48) at org.springframework.security.web.FilterChainProxy$VirtualFilterChain.doFilter(FilterChainProxy.java:330) at org.springframework.security.web.authentication.www.BasicAuthenticationFilter.doFilterInternal(BasicAuthenticationFilter.java:158) at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107) at org.springframework.security.web.FilterChainProxy$VirtualFilterChain.doFilter(FilterChainProxy.java:330) at datameer.dap.conductor.authentication.CompositeAuthenticationFilter$InternalFilterChain.doFilter(CompositeAuthenticationFilter.java:64) at org.springframework.security.web.authentication.AbstractAuthenticationProcessingFilter.doFilter(AbstractAuthenticationProcessingFilter.java:205) at datameer.dap.conductor.authentication.CompositeAuthenticationFilter$InternalFilterChain.doFilter(CompositeAuthenticationFilter.java:68) at datameer.dap.conductor.authentication.CompositeAuthenticationFilter.doFilter(CompositeAuthenticationFilter.java:49) at org.springframework.security.web.FilterChainProxy$VirtualFilterChain.doFilter(FilterChainProxy.java:330) at datameer.dap.conductor.webapp.controller.fte.AccessTokenBasedAuthenticationProcessingFilter.doFilter(AccessTokenBasedAuthenticationProcessingFilter.java:94) at org.springframework.security.web.FilterChainProxy$VirtualFilterChain.doFilter(FilterChainProxy.java:330) at datameer.dap.conductor.webapp.filter.AutoAdminAuthenticationFilter.doFilter(AutoAdminAuthenticationFilter.java:65) at org.springframework.security.web.FilterChainProxy$VirtualFilterChain.doFilter(FilterChainProxy.java:330) at org.springframework.security.web.authentication.logout.LogoutFilter.doFilter(LogoutFilter.java:120) at org.springframework.security.web.FilterChainProxy$VirtualFilterChain.doFilter(FilterChainProxy.java:330) at org.springframework.security.web.context.request.async.WebAsyncManagerIntegrationFilter.doFilterInternal(WebAsyncManagerIntegrationFilter.java:53) at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107) at org.springframework.security.web.FilterChainProxy$VirtualFilterChain.doFilter(FilterChainProxy.java:330) at org.springframework.security.web.context.SecurityContextPersistenceFilter.doFilter(SecurityContextPersistenceFilter.java:91) at org.springframework.security.web.FilterChainProxy$VirtualFilterChain.doFilter(FilterChainProxy.java:330) at org.springframework.security.web.FilterChainProxy.doFilterInternal(FilterChainProxy.java:213) at org.springframework.security.web.FilterChainProxy.doFilter(FilterChainProxy.java:176) at org.springframework.web.filter.DelegatingFilterProxy.invokeDelegate(DelegatingFilterProxy.java:344) at org.springframework.web.filter.DelegatingFilterProxy.doFilter(DelegatingFilterProxy.java:261) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.ClickJackingPreventionFilter.doFilter(ClickJackingPreventionFilter.java:40) at org.springframework.web.filter.DelegatingFilterProxy.invokeDelegate(DelegatingFilterProxy.java:344) at org.springframework.web.filter.DelegatingFilterProxy.doFilter(DelegatingFilterProxy.java:261) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at org.springframework.web.multipart.support.MultipartFilter.doFilterInternal(MultipartFilter.java:118) at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.OptimisticLockRetryFilter.doFilter(OptimisticLockRetryFilter.java:31) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.PermissionDeniedExceptionFilter.doFilter(PermissionDeniedExceptionFilter.java:29) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.RequestMetaDataFilter.doFilter(RequestMetaDataFilter.java:27) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.DeprecatedRestUrlsFilter.doFilter(DeprecatedRestUrlsFilter.java:90) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.BrowserExceptionFilter.doFilter(BrowserExceptionFilter.java:31) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.RestExceptionFilter.doFilter(RestExceptionFilter.java:30) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.NoResultExceptionFilter.doFilter(NoResultExceptionFilter.java:24) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.DasExceptionFilter.doFilter(DasExceptionFilter.java:29) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at org.springframework.web.filter.CharacterEncodingFilter.doFilterInternal(CharacterEncodingFilter.java:85) at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at org.springframework.web.filter.RequestContextFilter.doFilterInternal(RequestContextFilter.java:99) at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.webapp.filter.RequestContextFilter.doFilter(RequestContextFilter.java:43) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at datameer.dap.conductor.authentication.FailedLoginServletFilter.doFilter(FailedLoginServletFilter.java:63) at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652) at org.eclipse.jetty.servlet.ServletHandler.doHandle(ServletHandler.java:585) at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:143) at org.eclipse.jetty.security.SecurityHandler.handle(SecurityHandler.java:577) at org.eclipse.jetty.server.session.SessionHandler.doHandle(SessionHandler.java:223) at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:143) at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:97) at com.jamonapi.http.JAMonJettyHandlerNew.handle(JAMonJettyHandlerNew.java:36) at org.eclipse.jetty.server.handler.ContextHandler.doHandle(ContextHandler.java:1129) at org.eclipse.jetty.servlet.ServletHandler.doScope(ServletHandler.java:515) at org.eclipse.jetty.server.session.SessionHandler.doScope(SessionHandler.java:185) at org.eclipse.jetty.server.handler.ContextHandler.doScope(ContextHandler.java:1061) at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:141) at org.eclipse.jetty.server.handler.ContextHandlerCollection.handle(ContextHandlerCollection.java:215) at org.eclipse.jetty.server.handler.HandlerCollection.handle(HandlerCollection.java:110) at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:97) at org.eclipse.jetty.server.Server.handle(Server.java:497) at org.eclipse.jetty.server.HttpChannel.handle(HttpChannel.java:310) at org.eclipse.jetty.server.HttpConnection.onFillable(HttpConnection.java:257) at org.eclipse.jetty.io.AbstractConnection$2.run(AbstractConnection.java:540) at org.eclipse.jetty.util.thread.QueuedThreadPool.runJob(QueuedThreadPool.java:635) at org.eclipse.jetty.util.thread.QueuedThreadPool$3.run(QueuedThreadPool.java:555) at java.lang.Thread.run(Thread.java:745)Caused by: javax.mail.MessagingException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target; nested exception is: javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target at com.sun.mail.imap.IMAPStore.protocolConnect(IMAPStore.java:571) at javax.mail.Service.connect(Service.java:288) at javax.mail.Service.connect(Service.java:169) at datameer.das.plugins.mail.MailConnectionFactory.connectWithRetriesOnTimeout(MailConnectionFactory.java:139) at datameer.das.plugins.mail.MailConnectionFactory.getAndConnectMailStore(MailConnectionFactory.java:131) at datameer.das.plugins.mail.MailConnectionFactory.getMailStore(MailConnectionFactory.java:56) at datameer.das.plugins.mail.MailDataStoreModel.testConnect(MailDataStoreModel.java:79) ... 159 moreCaused by: javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target at sun.security.ssl.Alerts.getSSLException(Alerts.java:192) at sun.security.ssl.SSLSocketImpl.fatal(SSLSocketImpl.java:1884) at sun.security.ssl.Handshaker.fatalSE(Handshaker.java:276) at sun.security.ssl.Handshaker.fatalSE(Handshaker.java:270) at sun.security.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1341) at sun.security.ssl.ClientHandshaker.processMessage(ClientHandshaker.java:153) at sun.security.ssl.Handshaker.processLoop(Handshaker.java:868) at sun.security.ssl.Handshaker.process_record(Handshaker.java:804) at sun.security.ssl.SSLSocketImpl.readRecord(SSLSocketImpl.java:1016) at sun.security.ssl.SSLSocketImpl.performInitialHandshake(SSLSocketImpl.java:1312) at sun.security.ssl.SSLSocketImpl.readDataRecord(SSLSocketImpl.java:882) at sun.security.ssl.AppInputStream.read(AppInputStream.java:102) at com.sun.mail.util.TraceInputStream.read(TraceInputStream.java:110) at java.io.BufferedInputStream.fill(BufferedInputStream.java:235) at java.io.BufferedInputStream.read(BufferedInputStream.java:254) at com.sun.mail.iap.ResponseInputStream.readResponse(ResponseInputStream.java:97) at com.sun.mail.iap.Response.<init>(Response.java:96) at com.sun.mail.imap.protocol.IMAPResponse.<init>(IMAPResponse.java:61) at com.sun.mail.imap.protocol.IMAPResponse.readResponse(IMAPResponse.java:135) at com.sun.mail.imap.protocol.IMAPProtocol.readResponse(IMAPProtocol.java:261) at com.sun.mail.iap.Protocol.<init>(Protocol.java:114) at com.sun.mail.imap.protocol.IMAPProtocol.<init>(IMAPProtocol.java:104) at com.sun.mail.imap.IMAPStore.protocolConnect(IMAPStore.java:538) ... 165 moreCaused by: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target at sun.security.validator.PKIXValidator.doBuild(PKIXValidator.java:385) at sun.security.validator.PKIXValidator.engineValidate(PKIXValidator.java:292) at sun.security.validator.Validator.validate(Validator.java:260) at sun.security.ssl.X509TrustManagerImpl.validate(X509TrustManagerImpl.java:326) at sun.security.ssl.X509TrustManagerImpl.checkTrusted(X509TrustManagerImpl.java:231) at sun.security.ssl.X509TrustManagerImpl.checkServerTrusted(X509TrustManagerImpl.java:126) at sun.security.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1323) ... 183 moreCaused by: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target at sun.security.provider.certpath.SunCertPathBuilder.engineBuild(SunCertPathBuilder.java:196) at java.security.cert.CertPathBuilder.build(CertPathBuilder.java:268) at sun.security.validator.PKIXValidator.doBuild(PKIXValidator.java:380) ... 189 more