Automated Mail Through ICloud

We wanted to set up some infrastructure that would send mail through a shared icloud account. Here's how we did that:

Set up icloud account.
Set up AppleID for said icloud account / the mac(s) running the infrastructure.
Fully log in to your Apple ... stuff. Mac, icloud, apple ID, etc. You must use two-factor authentication to do so.
Go to your AppleID management interface, once fully logged in and authenticated.
Create an "app specific password."

You should now be fully set up and ready to go! Invoke your script. Let's assume your icloud account is myfakeaccount@icloud.com. This should be it!

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python mailer.py \
	--user myfakeaccount \
	--passwd <app specific password in the format: aaaa-aaaa-aaaa-aaaa> \
	--host smtp.mail.me.com \
	--port 587 \
	--from_addr myfakeaccount@icloud.com \
	--to_addr <your address> \
	--subj "Your subject" \
	--attach your_file.txt

If that doesn't work, well, check the reference document we used to get going and see what's wrong.

Ches Koblents