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I am still experiencing this issue where after about 3 or 4 hours, I can no longer log in and need to restart. The Jenkins log did not show any errors, but I tried using the Jenkins CLI and got a stack trace. Hopefully this can shed some light on the issue. I should note that our LDAP connection is an SSL connection through an F5 load balancer. Our certificates are signed by a CA, and I do have the trust store set up.
org.acegisecurity.AuthenticationServiceException: Unable to connect to LDAP server; nested exception is javax.naming.CommunicationException: <LDAP_VIP>:636 [Root exception is javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path validation failed: java.security.cert.CertPathValidatorException: Path does not chain with any of the trust anchors]; nested exception is org.acegisecurity.ldap.LdapDataAccessException: Unable to connect to LDAP server; nested exception is javax. naming.CommunicationException: <LDAP_VIP>:636 [Root exception is javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path validation failed: java.security.cert.CertPathValidatorException: Path does not chain with any of the trust anchors] at org.acegisecurity.providers.ldap.LdapAuthenticationProvider.retrieveUser(LdapAuthenticationProvider.java:238) at org.acegisecurity.providers.dao.AbstractUserDetailsAuthenticationProvider.authenticate(AbstractUserDetailsAuthenticationProvider.java:122) at org.acegisecurity.providers.ProviderManager.doAuthentication(ProviderManager.java:200) at org.acegisecurity.AbstractAuthenticationManager.authenticate(AbstractAuthenticationManager.java:47) at hudson.security.LDAPSecurityRealm$LDAPAuthenticationManager.authenticate(LDAPSecurityRealm.java:786) at hudson.security.LDAPSecurityRealm.authenticate(LDAPSecurityRealm.java:663) at hudson.security.AbstractPasswordBasedSecurityRealm.doAuthenticate(AbstractPasswordBasedSecurityRealm.java:114) at hudson.security.AbstractPasswordBasedSecurityRealm.access$100(AbstractPasswordBasedSecurityRealm.java:39) at hudson.security.AbstractPasswordBasedSecurityRealm$1.authenticate(AbstractPasswordBasedSecurityRealm.java:81) at hudson.cli.CLICommand.main(CLICommand.java:231) at hudson.cli.CliManagerImpl.main(CliManagerImpl.java:92) at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method) at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:57) at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) at java.lang.reflect.Method.invoke(Method.java:606) at hudson.remoting.RemoteInvocationHandler$RPCRequest.perform(RemoteInvocationHandler.java:326) at hudson.remoting.RemoteInvocationHandler$RPCRequest.call(RemoteInvocationHandler.java:301) at hudson.remoting.RemoteInvocationHandler$RPCRequest.call(RemoteInvocationHandler.java:260) at hudson.remoting.UserRequest.perform(UserRequest.java:121) at hudson.remoting.UserRequest.perform(UserRequest.java:49) at hudson.remoting.Request$2.run(Request.java:325) at hudson.remoting.InterceptingExecutorService$1.call(InterceptingExecutorService.java:68) at hudson.cli.CliManagerImpl$1.call(CliManagerImpl.java:63) at hudson.remoting.CallableDecoratorAdapter.call(CallableDecoratorAdapter.java:18) at hudson.remoting.CallableDecoratorList$1.call(CallableDecoratorList.java:21) at jenkins.util.ContextResettingExecutorService$2.call(ContextResettingExecutorService.java:46) at java.util.concurrent.FutureTask.run(FutureTask.java:262) at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1145) at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:615) at java.lang.Thread.run(Thread.java:745) Caused by: org.acegisecurity.ldap.LdapDataAccessException: Unable to connect to LDAP server; nested exception is javax.naming.CommunicationException: <LDAP_VIP>:636 [Root exception is javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path validation failed: java.security.cert.CertPathValidatorException: Path does not chain with any of the trust anchors] at org.acegisecurity.ldap.DefaultInitialDirContextFactory.connect(DefaultInitialDirContextFactory.java:189) at org.acegisecurity.ldap.DefaultInitialDirContextFactory.newInitialDirContext(DefaultInitialDirContextFactory.java:247) at org.acegisecurity.ldap.LdapTemplate.execute(LdapTemplate.java:123) at org.acegisecurity.ldap.LdapTemplate.searchForSingleEntry(LdapTemplate.java:246) at org.acegisecurity.ldap.search.FilterBasedLdapUserSearch.searchForUser(FilterBasedLdapUserSearch.java:119) at org.acegisecurity.providers.ldap.authenticator.BindAuthenticator.authenticate(BindAuthenticator.java:71) at org.acegisecurity.providers.ldap.authenticator.BindAuthenticator2.authenticate(BindAuthenticator2.java:49) at org.acegisecurity.providers.ldap.LdapAuthenticationProvider.retrieveUser(LdapAuthenticationProvider.java:233) ... 29 more Caused by: javax.naming.CommunicationException: <LDAP_VIP>:636 [Root exception is javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path validation failed: java.security.cert.CertPathValidatorException: Path does not chain with any of the trust anchors] at com.sun.jndi.ldap.Connection.<init>(Connection.java:226) at com.sun.jndi.ldap.LdapClient.<init>(LdapClient.java:136) at com.sun.jndi.ldap.LdapClient.getInstance(LdapClient.java:1608) at com.sun.jndi.ldap.LdapCtx.connect(LdapCtx.java:2698) at com.sun.jndi.ldap.LdapCtx.<init>(LdapCtx.java:316) at com.sun.jndi.ldap.LdapCtxFactory.getUsingURL(LdapCtxFactory.java:193) at com.sun.jndi.ldap.LdapCtxFactory.getUsingURLs(LdapCtxFactory.java:211) at com.sun.jndi.ldap.LdapCtxFactory.getLdapCtxInstance(LdapCtxFactory.java:154) at com.sun.jndi.ldap.LdapCtxFactory.getInitialContext(LdapCtxFactory.java:84) at javax.naming.spi.NamingManager.getInitialContext(NamingManager.java:684) at javax.naming.InitialContext.getDefaultInitCtx(InitialContext.java:307) at javax.naming.InitialContext.init(InitialContext.java:242) at javax.naming.InitialContext.<init>(InitialContext.java:216) at javax.naming.directory.InitialDirContext.<init>(InitialDirContext.java:101) at org.acegisecurity.ldap.DefaultInitialDirContextFactory.connect(DefaultInitialDirContextFactory.java:180) ... 36 more Caused by: javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path validation failed: java.security.cert.CertPathValidatorException: Path does not chain with any of the trust anchors at sun.security.ssl.Alerts.getSSLException(Alerts.java:192) at sun.security.ssl.SSLSocketImpl.fatal(SSLSocketImpl.java:1904) at sun.security.ssl.Handshaker.fatalSE(Handshaker.java:279) at sun.security.ssl.Handshaker.fatalSE(Handshaker.java:273) at sun.security.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1446) at sun.security.ssl.ClientHandshaker.processMessage(ClientHandshaker.java:209) at sun.security.ssl.Handshaker.processLoop(Handshaker.java:901) at sun.security.ssl.Handshaker.process_record(Handshaker.java:837) at sun.security.ssl.SSLSocketImpl.readRecord(SSLSocketImpl.java:1023) at sun.security.ssl.SSLSocketImpl.performInitialHandshake(SSLSocketImpl.java:1332) at sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1359) at sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1343) at com.sun.jndi.ldap.Connection.createSocket(Connection.java:381) at com.sun.jndi.ldap.Connection.<init>(Connection.java:203) ... 50 more Caused by: sun.security.validator.ValidatorException: PKIX path validation failed: java.security.cert.CertPathValidatorException: Path does not chain with any of the trust anchors at sun.security.validator.PKIXValidator.doValidate(PKIXValidator.java:350) at sun.security.validator.PKIXValidator.engineValidate(PKIXValidator.java:249) 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:1428) ... 59 more Caused by: java.security.cert.CertPathValidatorException: Path does not chain with any of the trust anchors at sun.security.provider.certpath.PKIXCertPathValidator.engineValidate(PKIXCertPathValidator.java:208) at java.security.cert.CertPathValidator.validate(CertPathValidator.java:279) at sun.security.validator.PKIXValidator.doValidate(PKIXValidator.java:345) ... 65 more