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I have the same problem
I am encountering the same problem with 5.6a. In the log file it would state:
Connecting to SMTP server 'smtp.mymailserver.com' on port 25
Unspecified error
(Our smtp mail server requires no authentication)
If I keep trying, then it would be successful and the email is sent. Once it's successfull, it does not seem to fail again.
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