Apart from what davido said: I'm quite sure your problem is due to them (sensibly) requiring TLS for LOGIN (and you should probably use Port 587 for that). You'll have to manually use Net::SMTP::SSL to send the mail prepared by MIME::Lite because the latter doesn't support dependency injection, i.e. has no way for the user to specify their own Net::SMTP API-compatible module.

In reply to Re: SMTP auth() command not supported on smtp.live.com by mbethke
in thread SMTP auth() command not supported on smtp.live.com by lighterjoul

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