Error when sending email notifications from Jira

Bryan Boone
I'm New Here
I'm New Here
Those new to the Atlassian Community have posted less than three times. Give them a warm welcome!
August 14, 2022

So I have a Windows 2012 server with Jira server only.  The server seems to work fine, except for sending email notifications.  I am using smtp.office365.com for the smtp outgoing.

If I disable TLS, the test connection seems to work successfully.  If I enable TLS, it fails.

IOException: DerInputStream.getLength(): lengthTag=109, too big.

If I try to send a test email with TLS enabled, I get Error 1 below.

If I try to send a test email without TLS enabled, I get Error 2 below.

 

I read an article on this error, but everything is pretty cryptic.  Do I really need to regenerate all the SSL certs and get them signed again, and re-import the into the keystore and all that?

It's so confusing.  Not sure what to do to get the emails working.

Please help.

 

Error 1

An error has occurred with sending the test email:
com.atlassian.mail.MailException: javax.mail.MessagingException: Could not convert socket to TLS;
nested exception is:
java.net.SocketException: java.security.NoSuchAlgorithmException: Error constructing implementation (algorithm: Default, provider: SunJSSE, class: sun.security.ssl.SSLContextImpl$DefaultSSLContext)
at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:224)
.
.
.
at java.lang.Thread.run(Thread.java:748)
Caused by: javax.mail.MessagingException: Could not convert socket to TLS;
nested exception is:
java.net.SocketException: java.security.NoSuchAlgorithmException: Error constructing implementation (algorithm: Default, provider: SunJSSE, class: sun.security.ssl.SSLContextImpl$DefaultSSLContext)
at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:2140)
at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:734)
at javax.mail.Service.connect(Service.java:342)
at javax.mail.Service.connect(Service.java:222)
at javax.mail.Service.connect(Service.java:243)
at com.atlassian.mail.server.InternalAuthenticationContext.connectService(InternalAuthenticationContext.java:35)
at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:196)
... 282 more
Caused by: java.net.SocketException: java.security.NoSuchAlgorithmException: Error constructing implementation (algorithm: Default, provider: SunJSSE, class: sun.security.ssl.SSLContextImpl$DefaultSSLContext)
at javax.net.ssl.DefaultSSLSocketFactory.throwException(SSLSocketFactory.java:248)
at javax.net.ssl.DefaultSSLSocketFactory.createSocket(SSLSocketFactory.java:270)
at com.sun.mail.util.SocketFetcher.startTLS(SocketFetcher.java:528)
at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:2135)
... 288 more
Caused by: java.security.NoSuchAlgorithmException: Error constructing implementation (algorithm: Default, provider: SunJSSE, class: sun.security.ssl.SSLContextImpl$DefaultSSLContext)
at java.security.Provider$Service.newInstance(Provider.java:1617)
at sun.security.jca.GetInstance.getInstance(GetInstance.java:236)
at sun.security.jca.GetInstance.getInstance(GetInstance.java:164)
at javax.net.ssl.SSLContext.getInstance(SSLContext.java:156)
at javax.net.ssl.SSLContext.getDefault(SSLContext.java:96)
at javax.net.ssl.SSLSocketFactory.getDefault(SSLSocketFactory.java:122)
at com.sun.mail.util.SocketFetcher.startTLS(SocketFetcher.java:523)
... 289 more
Caused by: java.io.IOException: DerInputStream.getLength(): lengthTag=109, too big.
.
.
.

 

 


Error 2

An error has occurred with sending the test email:
com.atlassian.mail.MailException: com.sun.mail.smtp.SMTPSendFailedException: 451 5.7.3 STARTTLS is required to send mail [BL0PR02CA0128.namprd02.prod.outlook.com]

at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:224)
at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:176)
at com.atlassian.jira.plugins.mail.webwork.SendTestMail.doExecute(SendTestMail.java:95)
at webwork.action.ActionSupport.execute(ActionSupport.java:165)
.
.
.
at java.lang.Thread.run(Thread.java:748)
Caused by: com.sun.mail.smtp.SMTPSendFailedException: 451 5.7.3 STARTTLS is required to send mail [BL0PR02CA0128.namprd02.prod.outlook.com]

at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2374)
at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1808)
at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1285)
at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendMimeMessage(SMTPMailServerImpl.java:242)
at com.atlassian.mail.server.managers.EventAwareSMTPMailServer.sendMimeMessage(EventAwareSMTPMailServer.java:30)
at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:198)
... 282 more

 

 

1 answer

0 votes
Fabio Racobaldo _Herzum_
Community Leader
Community Leader
Community Leaders are connectors, ambassadors, and mentors. On the online community, they serve as thought leaders, product experts, and moderators.
March 19, 2023

Suggest an answer

Log in or Sign up to answer