Python script to send mail via Apple's iCloud. Be sure to setup an app specific password for and do not use or expose your iCloud password. https://support.apple.com/en-us/HT204397

smtp_icloud.py

import smtplib

#email.mime.multipart is specific to python3
from email.mime.multipart import MIMEMultipart
from email.mime.text import MIMEText

msg = MIMEMultipart()
msg['From'] = '[email protected]'
msg['To'] = '[email protected]'
msg['Subject'] = 'Subject'
message = 'Message body'
msg.attach(MIMEText(message))

mailserver = smtplib.SMTP('smtp.mail.me.com', 587)
# identify ourselves
mailserver.ehlo()
# secure our email with tls encryption
mailserver.starttls()
# re-identify ourselves as an encrypted connection
mailserver.ehlo()
mailserver.login('iCloud ID', 'app-specific password')
mailserver.sendmail('[email protected]',
                    '[email protected]', msg.as_string())

mailserver.quit()