SMTP not working after upgrade

After upgrading from Confluence 3.5.5 to 5.1.5 and moving from a Windows 2003 server to a Windows 2008 server this weekend, SMTP email no longer works. I get the following error when trying to send a test message:

An error has occurred with sending the test email. If your mail server requires authentication, please ensure that TLS or SSL is enabled on your server for the specific mailbox. If your mail server allows anonymous connection, please remove the username and password from the configuration and try again.

com.atlassian.mail.MailException: javax.mail.AuthenticationFailedException: No authentication mechansims supported by both server and client
	at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:193)
[truncated]

At the suggestion of our Exchange admin, I removed the username and password that had, until the upgrade, worked fine for authentication. He said anonymous would work internally. Then I got this error:

An error has occurred with sending the test email:
com.atlassian.mail.MailException: javax.mail.AuthenticationFailedException: failed to connect, no user name specified?
	at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:193)
	at com.atlassian.confluence.jmx.JmxSMTPMailServer.send(JmxSMTPMailServer.java:80)
	at com.atlassian.confluence.admin.actions.mail.SendTestEmailAction.execute(SendTestEmailAction.java:58)
[truncated]

I thought McAfee might be blocking the sending, but I confirmed it was configured to warn only, not block. I would appreciate any suggestions.

1 answer

1 accepted

After discovering this issue (https://jira.atlassian.com/browse/CONF-29000), I created a new SMTP configuration from scratch and was able to get anonymous sending to work.

Suggest an answer

Log in or Sign up to answer
Atlassian Community Anniversary

Happy Anniversary, Atlassian Community!

This community is celebrating its one-year anniversary and Atlassian co-founder Mike Cannon-Brookes has all the feels.

Read more
Community showcase
Kesha Thillainayagam
Posted Friday in Confluence

We want to hear how your non-technical teams are using Confluence!

Hi Community! Kesha (kay-sha) from the Confluence marketing team here! Can you share stories with us on how your non-technical (think Marketing, Sales, HR, legal, etc.) teams are using Confluen...

301 views 11 10
Join discussion

Atlassian User Groups

Connect with like-minded Atlassian users at free events near you!

Find a group

Connect with like-minded Atlassian users at free events near you!

Find my local user group

Unfortunately there are no AUG chapters near you at the moment.

Start an AUG

You're one step closer to meeting fellow Atlassian users at your local meet up. Learn more about AUGs

Groups near you