On 23 Jun 2009, at 21:52, Jeff Laing wrote:
Ok, I'll bite.

How does the mail server that Mail.app is talking to distinguish between Mail.app and /usr/sbin/sendmail ? They both presumably just talk SMTP ?

Mail.app is configurable by the user to connect to a specific relay mail server, potentially using login credentials, SSL, and/or an alternate port. Sendmail, by contrast, is not configurable (without cracking open the terminal, at least), and will by default always connect directly to the destination mail server. It's this exact behavior that makes it unlikely to work properly.

Consider also that not all users even have Mail.app configured. An increasing number of users use online mail services such as GMail exclusively. In their case, not even scripting Mail.app will help you.

If you really need to deliver email notifications from an application, the only reliable solution is to put together a properly secured web- to-email gateway for your application somewhere and use that. Sending email directly from the desktop is no longer a viable solution without explicit configuration.
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