Issues with Configuring Email Server

There are two issues here:


1. You cannot send email using Send Email Smart Service
---> Error in logs: Caused by: javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?
---> Root cause: SSL handshake
---> Suggested solution #1

Use this value instead of yours and restart JBoss

conf.mailhandler.mail.transport.protocol=smtp

---> Suggested solution #2 if #1 doesn't work

leave smtps here:

conf.mailhandler.mail.transport.protocol=smtps

but make this false and restart JBoss

conf.mailhandler.mail.smtp.starttls.required=false



2. The system cannot send email alerts
---> Error in logs: Caused by: java.io.IOException: Invalid Http response
---> Root cause: This has to do with the settings I mentioned earlier. I still believe they're misconfigured.
---> Will investigate this once #1 is resolved

We implemented the first step and below is the error details :
==========================================================
07:14:44,206 INFO [stdout] (Appian Work Item - 1 - NotificationsEmail : MailRequest) 2015-09-22 07:14:44,206 [Appian Work Item - 1 - NotificationsEmail : MailRequest] ERROR com.appiancorp.ap2.util.Mail - Could not send mail via smtp.office365.com:587 to user2@xyz.com

07:14:44,208 ERROR [org.jboss.as.ejb3.invocation] (Appian Work Item - 1 - NotificationsEmail) JBAS014134: EJB Invocation failed on component UnattendedRequestHandlerBean for method public abstract com.appiancorp.process.engine.ContinuationResponse com.appiancorp.ra.workpoller.UnattendedRequestListener.onMessage(com.appiancorp.process.engine.UnattendedRequest): javax.ejb.EJBException: com.appiancorp.process.engine.EmailSendException: Could not send email from user1@xyz.com to user2@xyz.com subject Error in Task: Send E-Mail

Caused by: com.appiancorp.process.engine.EmailSendException: Could not send email from user1@xyz.com to user2@xyz.com subject Error in Task: Send E-Mail

Caused by: javax.mail.AuthenticationFailedException: 535 5.7.3 Authentication unsuccessful

07:14:44,273 INFO [stdout] (default-threads - 49) 2015-09-22 07:14:44,260 [default-threads - 49] ERROR com.appiancorp.ra.workpoller.WorkItemListener - The following exception occurred while attempting to complete work item [(WorkId: 6, WorkType: [AbstractMailRequest: from=user1@xyz.com, to=user2@xyz.com, subject=Error in Task: Send E-Mail], Response: null, ServerName: NotificationsEmail)] - Exception:

07:14:44,274 INFO [stdout] (default-threads - 49) javax.resource.spi.work.WorkCompletedException: com.appiancorp.process.engine.EmailSendException: Could not send email from user1@xyz.com to user2@xyz.com subject Error in Task: Send E-Mail
========================================================

We specified the password for user1 in passwords.properties under

=================================================
## The password used to connect to the SMTP server configured in
## conf.mailhandler.mail.smtp.host in custom.properties
conf.password.SMTP=<Password for Sender (user 1) to for connecting to the Mail Server >

@Eduardo : Please have a look into the above details and let us know the further proceedings.

It seems we're making progress, we no longer get the SSL error because we configured Appian not to fail if the mail server doesn't support SSL.

Now you need to troubleshoot the authentication problem.

I suggest you verify the syntax for the username and the password. No domain is required at all in the username.

I also suggest you retry creating the passwords.properties

@Eduardo :

We still getting authentication unsuccessful even after removing the domain name for the user as below :-
=======================================================================================================

05:15:16,967 INFO [stdout] (http-/0.0.0.0:8080-1) 2015-09-23 05:15:16,964 [http-/0.0.0.0:8080-1] ERROR com.appiancorp.ap2.util.Mail - Could not send mail via mail.office365.com:587 to user2@xyz.com

05:15:16,979 INFO [stdout] (http-/0.0.0.0:8080-1) 2015-09-23 05:15:16,974 [http-/0.0.0.0:8080-1] ERROR com.appiancorp.process.runtime.activities.SendEmailActivity - javax.mail.AuthenticationFailedException: 535 5.7.3 Authentication unsuccessful

=======================================================================================================

Attaching custom.properties file and passwords.properties files for more details .

I've seen this exact same issue before when the format in which you're passing the username is not correct. Since you're removing the values from custom.properties I cannot tell.

Can you paste here the value of this setting

conf.mailhandler.mail.user=

since the password is unknown pasting the user here is not a risk.

conf.mailhandler.mail.user=vamsib

Have you tried using the full email ID? support.office.com/.../What-is-my-user-ID-and-why-do-I-need-it-for-Office-365-for-business-37da662b-5da6-4b56-a091-2731b2ecc8b4

When I said: Remove the domain I thought you had something like this

conf.mailhandler.mail.user=ABC.COM\\vamsib

but since we now fixed the SSL error I suggest something like this

conf.mailhandler.mail.user=vamsib@.........

After mentioning the fully qualified user with domain name , we are getting the below error :
=================================================================================
08:06:20,688 INFO [stdout] (http-/0.0.0.0:8080-2) 2015-09-23 08:06:20,687 [http-/0.0.0.0:8080-2] ERROR com.appiancorp.ap2.util.Mail - Could not send mail via mail.office365.com:587 to

08:06:20,723 INFO [stdout] (http-/0.0.0.0:8080-2) 2015-09-23 08:06:20,713 [http-/0.0.0.0:8080-2] ERROR com.appiancorp.process.runtime.activities.SendEmailActivity - com.sun.mail.smtp.SMTPSendFailedException: 501 5.1.7 Invalid address