Python · Sending Email

For an encrypted SMTP connection, what's the difference between smtplib.SMTP with .starttls() and smtplib.SMTP_SSL — including the typical port for each?

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More in Sending Email

You want your Python script to SEND an outgoing email. Which standard-library module connects to the mail server, and which protocol does it speak?

You connect with smtplib.SMTP(host, 587), then immediately call .login(...) over the plain connection. Why is this a problem, and what step is missing?

What does smtp.sendmail(...) return when ALL recipients accepted the message, and how would a competent dev wrongly interpret it?

In smtp.sendmail(from_addr, to_addrs, msg), you pass a single recipient string "a@b.com" as to_addrs and it works. Then you switch to two recipients — what's the gotcha?

What happens when you run this? ``` from email.message import EmailMessage m = EmailMessage() m["Subject"] = "Hi" m["Subject"] = "Bye" print(m["Subject"]) ```

Why prefer email.message.EmailMessage + .set_content(...) over hand-building MIMEText/MIMEMultipart strings for a modern email?

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