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If I remember correctly, this was a bug I encountered while implementing advanced batch support for 6.0.0. I'll dive into the 5.x.y code for you somewhere this week to confirm.
Is there a reason why for synchronous calls no timeouts are configured?
The workaround is to set the timeouts via properties.
MailSender.send(final Email email, final boolean async)
...
if (async)
...
configureSessionWithTimeout(...)
I'm using SimpleJavaMail:5.4.0
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