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. 


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