Please see this post in the General GAE Group https://groups.google.com/group/google-appengine/browse_thread/thread/c9b98fb136eb7d02/fb53b9e4f5965875?hl=en#fb53b9e4f5965875
And this issue http://code.google.com/p/googleappengine/issues/detail?id=5776#c1 I have been having problems with the Email Service in Java and would really appreciate any advice anyone can give me. There are more details in the issue but in summary I have an app that sends email notifications when users make changes. The emails seemed to work only intermittently even though I wasn't changing anything. I get errors like the following; MessagingException: MailService IO failed (java.io.IOException: Internal error) javax.mail.SendFailedException: MailService IO failed (java.io.IOException: Internal error) at com.google.appengine.api.mail.stdimpl.GMTransport.sendMessage(GMTransport.java: 253) at javax.mail.Transport.send(Transport.java:95) at javax.mail.Transport.send(Transport.java:48) at com.hotf.server.EmailService$1.run(EmailService.java:119) I wrapped the code to send the emails in a deferred task queue that keeps trying every 15 minutes until it works without raising an exception and after a random amount of time (anything up to 8 hours) the emails are delivered successfully. -- You received this message because you are subscribed to the Google Groups "Google App Engine for Java" group. To view this discussion on the web visit https://groups.google.com/d/msg/google-appengine-java/-/WxJsiU2GMcIJ. To post to this group, send email to google-appengine-java@googlegroups.com. To unsubscribe from this group, send email to google-appengine-java+unsubscr...@googlegroups.com. For more options, visit this group at http://groups.google.com/group/google-appengine-java?hl=en.