Hyland Connect

skri1979 · ‎11-03-2010

I find configuring OutboundSMTP Settings quite confusing.
Yes, I read the WIki.
And yes, I browsed the Community Forum for this topic.
But still I can't find any solution.

I tested alfresco community version 4.3.a on WinXP SP3 and on Debian Lenny.
I'm testing on a local machine. Not in the internet. (Maybe this is the problem…)
On none of the test-installations, I got Outbound SMTP running.

As far as I see, the Problem is that the SMTP Client does not authenticate on the email server.
But toggling smtp.auth = true or false makes no difference…

Is there any other file to be touched than global properties and the custom email context?

Thanks in advance for your help.

Kindest regards.
K.

Here is the alfresco global properties part for mail

###Mail ###
mail.host=xxx
mail.port=25
mail.username=xxx
mail.password=xxx
mail.encoding=UTF-8
mail.from.default=xxx
mail.smtp.auth=true
mail.smtp.timeout=30000
mail.smtp.starttls.enable=false
mail.protocol=smtp
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Here is the custom email context.xml

<?xml version='1.0' encoding='UTF-8'?>
<!DOCTYPE beans PUBLIC '-//SPRING//DTD BEAN//EN' 'http://www.springframework.org/dtd/spring-beans.dtd'>

<beans>
<!–                        –>
<!– MAIL SERVICE           –>
<!–                        –>

<bean id="mailService" class="org.springframework.mail.javamail.JavaMailSenderImpl">
    <property name="host">
        <value>${mail.host}</value>
    </property>
    <property name="port">
        <value>${mail.port}</value>
    </property>
    <property name="protocol">
        <value>${mail.protocol}</value>
    </property>
    <property name="username">
        <value>${mail.username}</value>
    </property>
    <property name="password">
        <value>${mail.password}</value>
    </property>
    <property name="defaultEncoding">
        <value>${mail.encoding}</value>
    </property>
    <property name="javaMailProperties">
        <props>
            <prop key="mail.smtp.auth">${mail.smtp.auth}</prop>
            <prop key="mail.smtp.starttls.enable">${mail.smtp.starttls.enable}</prop>

        </props>
    </property>
</bean>
</beans>
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Here is the last part of tomcat Log.


Caused by: org.springframework.mail.MailSendException; nested exceptions (1) are:
Failed message 1: javax.mail.SendFailedException: Invalid Addresses;
  nested exception is:
   com.sun.mail.smtp.SMTPAddressFailedException: 550 must be authenticated

   at org.springframework.mail.javamail.JavaMailSenderImpl.doSend(JavaMailSenderImpl.java:421)
   at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:341)
   at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:356)
   at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:345)
   at org.alfresco.repo.action.executer.MailActionExecuter.executeImpl(MailActionExecuter.java:439)
   … 144 more
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skri1979 · ‎11-03-2010

After some further testing…Is there a bug with "smtp.auth = true/false"?

Or must I touch files in the subsystems > email > xxx

ahbao · ‎11-03-2010

mine works fine with the changes in tomcat\shared\classes\alfresco-global.properties

#
# Outbound Email Configuration
#————-
mail.host=xxx
mail.port=25
mail.username=xxx
mail.password=xxx
mail.encoding=UTF-8
mail.from.default=xxx
mail.smtp.auth=true

Are you able to check your mail server log to confirm the problem?

skri1979 · ‎11-04-2010

Hi there,
thanks for you answer.

I re-chacked the mail settings in my mail programm.
In the mail client, everything works fine.

Maybe I should telnet from the maschine I installed alfresco on?

Kind regards,

K.

skri1979 · ‎11-04-2010

Strange. Strange.
Even telnet works…

Must I encode username and password?
Base64? Or something like that?

Kind regards,
K.

ted220 · ‎11-07-2010

I have the same problem with the same results. I try different configurations and now I am giving up. I have the same log.

skri1979 · ‎11-07-2010

Hi there all,

now I set up a clean installation Debian Lenny and ran Alfresco CE.
Set up the OutBoundSMTP like described above…AND IT WORKED!

My mistakes, as I found out afterwards, were
a) mailing with a FROM Adress not available (freely inspired)
b) mailing TO the email Adress which I wanted to invite
c) mailing from a server with no domain name set.

Hope this helps.

captnbob · ‎11-22-2010

Hi Skri

Can you give a bit more info on your 'mistakes' listed, please.

a) was the FROM address not available on the mail server?
b) were you sending the invite to the address used to send the mail from?
c) did setting the domain on Debian solve the problem?

I'm using Ubuntu 10.04 with Alfresco CE 3.4b. The same happened with 3.4a. I previously used 3.3g but didn't use email for invitations, so I'm not sure if this was a problem.

These are my parameters in the file alfresco-global.properties


# Email configuration
mail.host=mail.companyx.com
mail.port=587
mail.username=xxxx@companyx.com
mail.password=xxxpasswordxxx
mail.encoding=UTF-8
mail.header=
mail.from.default=xxxx@companyx.com
mail.smtp.auth=true
mail.smtp.timeout=30000
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I can send mail using the email account, using Outlook with matching parameters, but using Alfresco, I get this error:


16:52:26,820 ERROR [org.alfresco.repo.action.executer.MailActionExecuter] Failed to send email to xxxx@companyx.com
org.springframework.mail.MailSendException; nested exception details (1) are:
Failed message 1:
com.sun.mail.smtp.SMTPSendFailedException: 550 Submission must be authenticated

        at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:1388)
        at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:959)
        at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:583)
        at org.springframework.mail.javamail.JavaMailSenderImpl.doSend(JavaMailSenderImpl.java:402)
        at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:341)
        at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:356)
        at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:345)
        at org.alfresco.repo.action.executer.MailActionExecuter.executeImpl(MailActionExecuter.java:439)
        at org.alfresco.repo.action.executer.ActionExecuterAbstractBase.execute(ActionExecuterAbstractBase.java:133)
        at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
        at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39)
        at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
        at java.lang.reflect.Method.invoke(Method.java:597)
        at org.alfresco.repo.management.subsystems.SubsystemProxyFactory$1.invoke(SubsystemProxyFactory.java:65)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:172)
        at org.springframework.aop.framework.JdkDynamicAopProxy.invoke(JdkDynamicAopProxy.java:202)
        at $Proxy243.execute(Unknown Source)
        at org.alfresco.repo.action.ActionServiceImpl.directActionExecution(ActionServiceImpl.java:749)
        at org.alfresco.repo.action.ActionServiceImpl.executeActionImpl(ActionServiceImpl.java:675)
        at org.alfresco.repo.action.ActionServiceImpl.executeAction(ActionServiceImpl.java:540)
        at org.alfresco.repo.action.ActionServiceImpl.executeAction(ActionServiceImpl.java:526)
        at org.alfresco.repo.action.ActionServiceImpl.executeAction(ActionServiceImpl.java:758)
        at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
        at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39)
        at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
        at java.lang.reflect.Method.invoke(Method.java:597)
        at org.springframework.aop.support.AopUtils.invokeJoinpointUsingReflection(AopUtils.java:307)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.invokeJoinpoint(ReflectiveMethodInvocation.java:183)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:150)
        at org.alfresco.repo.security.permissions.impl.AlwaysProceedMethodInterceptor.invoke(AlwaysProceedMethodInterceptor.java:34)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:172)
        at org.alfresco.repo.security.permissions.impl.ExceptionTranslatorMethodInterceptor.invoke(ExceptionTranslatorMethodInterceptor.java:44)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:172)
        at org.alfresco.repo.audit.AuditMethodInterceptor.proceed(AuditMethodInterceptor.java:160)
        at org.alfresco.repo.audit.AuditMethodInterceptor.invoke(AuditMethodInterceptor.java:137)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:172)
        at org.springframework.transaction.interceptor.TransactionInterceptor.invoke(TransactionInterceptor.java:107)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:172)
        at org.springframework.aop.framework.JdkDynamicAopProxy.invoke(JdkDynamicAopProxy.java:202)
        at $Proxy37.executeAction(Unknown Source)
        at org.alfresco.repo.invitation.site.InviteSender.sendMail(InviteSender.java:117)
        at org.alfresco.repo.invitation.site.SendInviteAction.execute(SendInviteAction.java:82)
        at org.jbpm.graph.def.Action.execute(Action.java:129)
        at org.jbpm.graph.def.GraphElement.executeAction(GraphElement.java:284)
        at org.jbpm.graph.def.GraphElement.executeActions(GraphElement.java:241)
        at org.jbpm.graph.def.GraphElement.fireAndPropagateEvent(GraphElement.java:213)
        at org.jbpm.graph.def.GraphElement.fireEvent(GraphElement.java:196)
        at org.jbpm.graph.def.Transition.take(Transition.java:152)
        at org.jbpm.graph.def.Node.leave(Node.java:479)
        at org.jbpm.graph.node.StartState.leave(StartState.java:82)
        at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
        at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39)
        at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
        at java.lang.reflect.Method.invoke(Method.java:597)
        at org.hibernate.proxy.pojo.cglib.CGLIBLazyInitializer.invoke(CGLIBLazyInitializer.java:157)
        at org.jbpm.graph.def.Node$$EnhancerByCGLIB$$d1a3b24f.leave(<generated>)
        at org.jbpm.graph.exe.Token.signal(Token.java:223)
        at org.jbpm.graph.exe.Token.signal(Token.java:188)
        at org.jbpm.taskmgmt.exe.TaskInstance.end(TaskInstance.java:495)
        at org.alfresco.repo.workflow.jbpm.WorkflowTaskInstance.end(WorkflowTaskInstance.java:135)
        at org.jbpm.taskmgmt.exe.TaskInstance.end(TaskInstance.java:436)
        at org.alfresco.repo.workflow.jbpm.JBPMEngine$26.doInJbpm(JBPMEngine.java:1815)
        at org.springmodules.workflow.jbpm31.JbpmTemplate$1.doInHibernate(JbpmTemplate.java:87)
        at org.springframework.orm.hibernate3.HibernateTemplate.doExecute(HibernateTemplate.java:406)
        at org.springframework.orm.hibernate3.HibernateTemplate.execute(HibernateTemplate.java:339)
        at org.springmodules.workflow.jbpm31.JbpmTemplate.execute(JbpmTemplate.java:80)
        at org.alfresco.repo.workflow.jbpm.JBPMEngine.endTask(JBPMEngine.java:1780)
        at org.alfresco.repo.workflow.WorkflowServiceImpl.endTask(WorkflowServiceImpl.java:648)
        at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
        at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39)
        at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
        at java.lang.reflect.Method.invoke(Method.java:597)
        at org.springframework.aop.support.AopUtils.invokeJoinpointUsingReflection(AopUtils.java:307)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.invokeJoinpoint(ReflectiveMethodInvocation.java:183)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:150)
        at org.alfresco.repo.security.permissions.impl.AlwaysProceedMethodInterceptor.invoke(AlwaysProceedMethodInterceptor.java:34)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:172)
        at org.alfresco.repo.security.permissions.impl.ExceptionTranslatorMethodInterceptor.invoke(ExceptionTranslatorMethodInterceptor.java:44)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:172)
        at org.alfresco.repo.audit.AuditMethodInterceptor.proceed(AuditMethodInterceptor.java:160)
        at org.alfresco.repo.audit.AuditMethodInterceptor.invoke(AuditMethodInterceptor.java:137)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:172)
        at org.springframework.transaction.interceptor.TransactionInterceptor.invoke(TransactionInterceptor.java:107)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:172)
        at org.springframework.aop.framework.JdkDynamicAopProxy.invoke(JdkDynamicAopProxy.java:202)
        at $Proxy71.endTask(Unknown Source)
        at org.alfresco.repo.invitation.InvitationServiceImpl.startNominatedInvite(InvitationServiceImpl.java:1345)
        at org.alfresco.repo.invitation.InvitationServiceImpl.inviteNominated(InvitationServiceImpl.java:228)
        at org.alfresco.repo.invitation.InvitationServiceImpl.inviteNominated(InvitationServiceImpl.java:184)
        at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
        at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39)
        at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
        at java.lang.reflect.Method.invoke(Method.java:597)
        at org.springframework.aop.support.AopUtils.invokeJoinpointUsingReflection(AopUtils.java:307)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.invokeJoinpoint(ReflectiveMethodInvocation.java:183)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:150)
        at org.alfresco.repo.security.permissions.impl.AlwaysProceedMethodInterceptor.invoke(AlwaysProceedMethodInterceptor.java:34)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:172)
        at org.alfresco.repo.security.permissions.impl.ExceptionTranslatorMethodInterceptor.invoke(ExceptionTranslatorMethodInterceptor.java:44)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:172)
        at org.alfresco.repo.audit.AuditMethodInterceptor.proceedWithAudit(AuditMethodInterceptor.java:217)
        at org.alfresco.repo.audit.AuditMethodInterceptor.proceed(AuditMethodInterceptor.java:184)
        at org.alfresco.repo.audit.AuditMethodInterceptor.invoke(AuditMethodInterceptor.java:137)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:172)
        at org.springframework.transaction.interceptor.TransactionInterceptor.invoke(TransactionInterceptor.java:107)
        at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:172)
        at org.springframework.aop.framework.JdkDynamicAopProxy.invoke(JdkDynamicAopProxy.java:202)
        at $Proxy105.inviteNominated(Unknown Source)
        at org.alfresco.repo.site.script.Site.inviteNominated(Site.java:653)
        at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
        at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39)
        at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
        at java.lang.reflect.Method.invoke(Method.java:597)
        at org.mozilla.javascript.MemberBox.invoke(MemberBox.java:155)
        at org.mozilla.javascript.NativeJavaMethod.call(NativeJavaMethod.java:243)
        at org.mozilla.javascript.optimizer.OptRuntime.callN(OptRuntime.java:86)
        at org.mozilla.javascript.gen.c9._c1(file:/opt/alfresco-3.4.b/tomcat/webapps/alfresco/WEB-INF/classes/alfresco/templates/webscripts/org/alfresco/repository/site/invitation/invitation.post.json.js:99)
        at org.mozilla.javascript.gen.c9.call(file:/opt/alfresco-3.4.b/tomcat/webapps/alfresco/WEB-INF/classes/alfresco/templates/webscripts/org/alfresco/repository/site/invitation/invitation.post.json.js)
        at org.mozilla.javascript.optimizer.OptRuntime.callName0(OptRuntime.java:108)
        at org.mozilla.javascript.gen.c9._c0(file:/opt/alfresco-3.4.b/tomcat/webapps/alfresco/WEB-INF/classes/alfresco/templates/webscripts/org/alfresco/repository/site/invitation/invitation.post.json.js:134)
        at org.mozilla.javascript.gen.c9.call(file:/opt/alfresco-3.4.b/tomcat/webapps/alfresco/WEB-INF/classes/alfresco/templates/webscripts/org/alfresco/repository/site/invitation/invitation.post.json.js)
        at org.mozilla.javascript.ContextFactory.doTopCall(ContextFactory.java:393)
        at org.mozilla.javascript.ScriptRuntime.doTopCall(ScriptRuntime.java:2834)
        at org.mozilla.javascript.gen.c9.call(file:/opt/alfresco-3.4.b/tomcat/webapps/alfresco/WEB-INF/classes/alfresco/templates/webscripts/org/alfresco/repository/site/invitation/invitation.post.json.js)
        at org.mozilla.javascript.gen.c9.exec(file:/opt/alfresco-3.4.b/tomcat/webapps/alfresco/WEB-INF/classes/alfresco/templates/webscripts/org/alfresco/repository/site/invitation/invitation.post.json.js)
        at org.alfresco.repo.jscript.RhinoScriptProcessor.executeScriptImpl(RhinoScriptProcessor.java:472)
        at org.alfresco.repo.jscript.RhinoScriptProcessor.execute(RhinoScriptProcessor.java:190)
        at org.alfresco.repo.processor.ScriptServiceImpl.executeScript(ScriptServiceImpl.java:282)
        at org.alfresco.repo.web.scripts.RepositoryScriptProcessor.executeScript(RepositoryScriptProcessor.java:102)
        at org.springframework.extensions.webscripts.AbstractWebScript.executeScript(AbstractWebScript.java:982)
        at org.springframework.extensions.webscripts.DeclarativeWebScript.execute(DeclarativeWebScript.java:86)
        at org.alfresco.repo.web.scripts.RepositoryContainer$2.execute(RepositoryContainer.java:383)
        at org.alfresco.repo.transaction.RetryingTransactionHelper.doInTransaction(RetryingTransactionHelper.java:381)
        at org.alfresco.repo.web.scripts.RepositoryContainer.transactionedExecute(RepositoryContainer.java:436)
        at org.alfresco.repo.web.scripts.RepositoryContainer.transactionedExecuteAs(RepositoryContainer.java:466)
        at org.alfresco.repo.web.scripts.RepositoryContainer.executeScript(RepositoryContainer.java:304)
        at org.springframework.extensions.webscripts.AbstractRuntime.executeScript(AbstractRuntime.java:333)
        at org.springframework.extensions.webscripts.AbstractRuntime.executeScript(AbstractRuntime.java:189)
        at org.springframework.extensions.webscripts.servlet.WebScriptServlet.service(WebScriptServlet.java:118)
        at javax.servlet.http.HttpServlet.service(HttpServlet.java:717)
        at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:290)
        at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)
        at org.alfresco.web.app.servlet.GlobalLocalizationFilter.doFilter(GlobalLocalizationFilter.java:58)
        at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)
        at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)
        at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:233)
        at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:191)
        at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:127)
        at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:102)
        at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:109)
        at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:298)
        at org.apache.coyote.http11.Http11Processor.process(Http11Processor.java:852)
        at org.apache.coyote.http11.Http11Protocol$Http11ConnectionHandler.process(Http11Protocol.java:588)
        at org.apache.tomcat.util.net.JIoEndpoint$Worker.run(JIoEndpoint.java:489)
        at java.lang.Thread.run(Thread.java:619)
‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍‍

Has anyone got a suggestion how to solve this?

thanks
Brian

skri1979 · ‎11-23-2010

Hi Brian,

Hi Skri

Can you give a bit more info on your 'mistakes' listed, please.

a) was the FROM address not available on the mail server?
b) were you sending the invite to the address used to send the mail from?
c) did setting the domain on Debian solve the problem?

I'm using Ubuntu 10.04 with Alfresco CE 3.4b. The same happened with 3.4a. I previously used 3.3g but didn't use email for invitations, so I'm not sure if this was a problem.

These are my parameters in the file alfresco-global.properties

a) FROM Adress was available on the MAIL Server.
b) I think this was my very problem.
c) I set the domain during the install routine. It's right after the Computer Name. I don't know if it also refers to the so called fully qualified domain name.
Actually, I would use a very bare system like debian lenny or FreeBSD to set up.
In my opinion, Ubuntu is very fine Desktop System but less qualified for server applications than a "raw" Debian.

Since I'm also a newbie to Alfresco, the only comment on the error codes I can give is:
Check the OutboundSmtp Wiki on alfresco and furthermore: Check spelling and case-sensitive lower/uppercase letters!
Also: First time struggeld with the xml File and the smtps.auth thing. -> Check Wiki.
Maybe you set up a complete new email account and try it again with "fresh" data.

Hope this helps.
Good Luck.

K.