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I have a script which is performing a MySQL dump, and I want it to send an email if and when it fails. How can I make the sending of the email use TLS with a username/password, a special port, and an alternate SMTP host?

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Try sendEmail: http://caspian.dotconf.net/menu/Software/SendEmail/ it allows you to specify an SMTP server and port using the -s flag. TLS can be enabled using -o tls=yes and a username and password can be set using -o username=... and -o password=... respectively.

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