What’s up with Alfresco failing due to mail errors

Not sure how to troubleshoot this one as our Alfresco server suddenly decided it no longer wants to send mail (or let us do any operation that attempts to send mail, such as approving documents). I did attempt an upgrade from 4.2e to 4.2f (into a completely separate directory), but never even got the new version to start (that'll be a second question I'll be asking…). We also reissued our SSL mail server certificate yet again (original due to heartbleed, then another reissue due to a bad key, then a third reissue due to one of our devices not accepting the larger reissue key). Those are the only 2 even vaguely related things that come to mind. Error log snippet follows:

00:00:00,204 WARN [org.alfresco.repo.activities.feed.FeedNotifier]
FeedNotifier: Failed to process entry "Person mailuser".
org.springframework.beans.factory.BeanCreationException: Error
creating bean with name 'mail' defined in file
[C:\Alfresco\tomcat\webapps\alfresco\WEB-INF\classes\alfresco\subsystems\email\OutboundSMTP\outboundSMTP-context.xml]:
Invocation of init method failed; nested exception is
org.alfresco.error.AlfrescoRuntimeException: 03290001
email.outbound.err.send.failed at
org.springframework.beans.factory.support.AbstractAutowireCapableBeanFactory.initializeBean(AbstractAutowireCapableBeanFactory.java:1420)
at
org.springframework.beans.factory.support.AbstractAutowireCapableBeanFactory.doCreateBean(AbstractAutowireCapableBeanFactory.java:519)
at
org.springframework.beans.factory.support.AbstractAutowireCapableBeanFactory.createBean(AbstractAutowireCapableBeanFactory.java:456)
at
org.springframework.beans.factory.support.AbstractBeanFactory$1.getObject(AbstractBeanFactory.java:291)
at
org.springframework.beans.factory.support.DefaultSingletonBeanRegistry.getSingleton(DefaultSingletonBeanRegistry.java:222)
at
org.springframework.beans.factory.support.AbstractBeanFactory.doGetBean(AbstractBeanFactory.java:288)
at
org.springframework.beans.factory.support.AbstractBeanFactory.getBean(AbstractBeanFactory.java:190)
at
org.springframework.beans.factory.support.DefaultListableBeanFactory.preInstantiateSingletons(DefaultListableBeanFactory.java:580)
at
org.springframework.context.support.AbstractApplicationContext.finishBeanFactoryInitialization(AbstractApplicationContext.java:895)
at
org.springframework.context.support.AbstractApplicationContext.refresh(AbstractApplicationContext.java:425)
at
org.alfresco.repo.management.subsystems.ChildApplicationContextFactory$ApplicationContextState.start(ChildApplicationContextFactory.java:803)
at
org.alfresco.repo.management.subsystems.AbstractPropertyBackedBean.start(AbstractPropertyBackedBean.java:991)
at
org.alfresco.repo.management.subsystems.AbstractPropertyBackedBean.onApplicationEvent(AbstractPropertyBackedBean.java:530)
at
org.alfresco.repo.management.SafeApplicationEventMulticaster.multicastEventInternal(SafeApplicationEventMulticaster.java:209)
at
org.alfresco.repo.management.SafeApplicationEventMulticaster.multicastEvent(SafeApplicationEventMulticaster.java:180)
at
org.springframework.context.support.AbstractApplicationContext.publishEvent(AbstractApplicationContext.java:303)
at
org.springframework.context.support.AbstractApplicationContext.finishRefresh(AbstractApplicationContext.java:911)
at
org.springframework.context.support.AbstractApplicationContext.refresh(AbstractApplicationContext.java:428)
at
org.springframework.web.context.ContextLoader.createWebApplicationContext(ContextLoader.java:276)
at
org.springframework.web.context.ContextLoader.initWebApplicationContext(ContextLoader.java:197)
at
org.springframework.web.context.ContextLoaderListener.contextInitialized(ContextLoaderListener.java:47)
at
org.alfresco.web.app.ContextLoaderListener.contextInitialized(ContextLoaderListener.java:63)
at
org.apache.catalina.core.StandardContext.listenerStart(StandardContext.java:4939)
at
org.apache.catalina.core.StandardContext.startInternal(StandardContext.java:5434)
at
org.apache.catalina.util.LifecycleBase.start(LifecycleBase.java:150)
at
org.apache.catalina.core.ContainerBase.addChildInternal(ContainerBase.java:901)
at
org.apache.catalina.core.ContainerBase.addChild(ContainerBase.java:877)
at
org.apache.catalina.core.StandardHost.addChild(StandardHost.java:633)
at
org.apache.catalina.startup.HostConfig.deployWAR(HostConfig.java:976)
at
org.apache.catalina.startup.HostConfig$DeployWar.run(HostConfig.java:1653)
at
java.util.concurrent.Executors$RunnableAdapter.call(Executors.java:471)
at java.util.concurrent.FutureTask$Sync.innerRun(FutureTask.java:334)
at java.util.concurrent.FutureTask.run(FutureTask.java:166) at
java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1145)
at
java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:615)
at java.lang.Thread.run(Thread.java:724) Caused by:
org.alfresco.error.AlfrescoRuntimeException: 03290001
email.outbound.err.send.failed at
org.alfresco.repo.action.executer.MailActionExecuter.sendEmail(MailActionExecuter.java:958)
at
org.alfresco.repo.action.executer.MailActionExecuter.executeImpl(MailActionExecuter.java:490)
at
org.alfresco.repo.action.executer.MailActionExecuter$1.doWork(MailActionExecuter.java:424)
at
org.alfresco.repo.security.authentication.AuthenticationUtil.runAs(AuthenticationUtil.java:548)
at
org.alfresco.repo.action.executer.MailActionExecuter.init(MailActionExecuter.java:414)
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
org.springframework.beans.factory.support.AbstractAutowireCapableBeanFactory.invokeCustomInitMethod(AbstractAutowireCapableBeanFactory.java:1544)
at
org.springframework.beans.factory.support.AbstractAutowireCapableBeanFactory.invokeInitMethods(AbstractAutowireCapableBeanFactory.java:1485)
at
org.springframework.beans.factory.support.AbstractAutowireCapableBeanFactory.initializeBean(AbstractAutowireCapableBeanFactory.java:1417)
… 35 more Caused by: org.springframework.mail.MailSendException:
Mail server connection failed; nested exception is
javax.mail.MessagingException: Unexpected exception borrwoing
connection from pool; nested exception is:
java.util.NoSuchElementException: Could not create a validated
object, cause: ValidateObject failed. Failed messages:
javax.mail.MessagingException: Unexpected exception borrwoing
connection from pool; nested exception is:
java.util.NoSuchElementException: Could not create a validated
object, cause: ValidateObject failed; message exceptions (1) are:
Failed message 1: javax.mail.MessagingException: Unexpected exception
borrwoing connection from pool; nested exception is:
java.util.NoSuchElementException: Could not create a validated
object, cause: ValidateObject failed at
org.springframework.mail.javamail.JavaMailSenderImpl.doSend(JavaMailSenderImpl.java:400)
at
org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:340)
at
org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:336)
at
org.alfresco.repo.action.executer.MailActionExecuter.sendEmail(MailActionExecuter.java:929)
… 46 more Caused by: javax.mail.MessagingException: Unexpected
exception borrwoing connection from pool; nested exception is:
java.util.NoSuchElementException: Could not create a validated
object, cause: ValidateObject failed at
org.alfresco.repo.mail.AlfrescoJavaMailSender$PooledTransportWrapper.protocolConnect(AlfrescoJavaMailSender.java:214)
at javax.mail.Service.connect(Service.java:275) at
org.springframework.mail.javamail.JavaMailSenderImpl.doSend(JavaMailSenderImpl.java:389)
… 49 more Caused by: java.util.NoSuchElementException: Could not
create a validated object, cause: ValidateObject failed at
org.apache.commons.pool.impl.GenericKeyedObjectPool.borrowObject(GenericKeyedObjectPool.java:1234)
at
org.alfresco.repo.mail.AlfrescoJavaMailSender$PooledTransportWrapper.protocolConnect(AlfrescoJavaMailSender.java:205)
… 51 more

Oh, final note. I tried posting on the Alfresco forums, but it kept chopping off my error logs and randomly deleting my text. Is there a better resource than here or their forums?