mail.app and smtp
apple’s mail.app works fairly well. that is, until something goes wrong. i know—stating the obvious. but hang with me for a moment. if you’re sending outbound email over ssl and/or with authentication, things get messy quickly. for reasons unknown to me, apple hasn’t seen fit to provide any debugging information at all. nothing lands in the console log and certainly no description of the error is presented to you, the willing email sender. instead you receive a terse message: ‘Cannot send message using the server
i’ve done some digging with the help of the mail server itself, so perhaps if you’re getting this less than descriptive error, there is hope.
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