How to send an e-mail to the international address

Question

How to send an e-mail to the international address via smtplib in Python?

If I use the following code

    try:
        server = None

        msg = MIMEMultipart('alternative')
        msg['From'] = formataddr((from_email_name, from_email))
        msg['To'] = Header(to_email, 'utf-8')
        msg['Subject'] = Header(subject, 'utf-8')

        plain_text_part = MIMEText(plain_text_body, 'plain', _charset='utf-8')
        msg.attach(plain_text_part)

        html_part = MIMEText(html_body, 'html', _charset='utf-8')
        msg.attach(html_part)

        server = smtplib.SMTP(smtp_server)
        server.starttls()
        server.login(from_email, from_email_password)
        server.sendmail(from_email, to_email, msg.as_string())
    finally:
        if server is not None:
            server.quit()

then the script fails on the following line when I call this code with ñoñó1234@server.com e-mail as a destination address (to_email):

server.sendmail(from_email, to_email, msg.as_string())

Output

'ascii' codec can't encode character u'\xf1' in position 9: ordinal not in range(128)

However if I change the sendmail function call to the following

server.sendmail(from_email, to_email.encode('utf-8'), msg.as_string())

it fails with the following error:

{'\xc3\xb1o\xc3\xb1\xc3\xb31234@server.com': (555, '5.5.2 Syntax error. i7sm368361lbo.39 - gsmtp')}

I'm using GMail's SMTP server to send these e-mails.

How can I fix it?

Thanks in advance.

Try this : msg['To'] = str(Header(to_email, 'utf-8')) Tell me if this works. — Prav001, Dec 02 '15 at 11:22
@Prav001 Unfortunately, it doesn't work. Note that the application crashes on the `sendmail` function call — FrozenHeart, Dec 02 '15 at 11:55
May be you should try another encoding scheme other than `utf-8` ? — Iron Fist, Dec 02 '15 at 13:15
@Iron Fist UTF-16 doesn't work either -- `{'\xff\xfe\xf1\x00o\x00\xf1\x00\xf3\x001\x002\x003\x004\x00@\x00s\x00e\x00r\x00v\x00e\x00r\x00.\x00c\x00o\x00m\x00': (555, '5.5.2 Syntax error. qp7sm484744lbc.24 - gsmtp')}` — FrozenHeart, Dec 02 '15 at 13:17
Or...may be the format of the email address should be `Recipient Name ` ... taken from this http://stackoverflow.com/questions/4421866/cakephp-smtp-emails-syntax-error] .. — Iron Fist, Dec 02 '15 at 13:19
Because, the error you are getting is not a syntax error, but rather a protocol error message from GSMTP server... — Iron Fist, Dec 02 '15 at 13:22
@Iron Fist Already tried it via `msg['To'] = Header(formataddr((to_email, to_email)), 'utf-8')` -- it doesn't help — FrozenHeart, Dec 02 '15 at 13:22
I was talking about `to_email = 'Recipient Name '` .. something like that and same goes for `from_email` — Iron Fist, Dec 02 '15 at 13:30
Read this : http://blog.yimingliu.com/2008/11/26/email-servers-and-mail-from-syntax/ — Iron Fist, Dec 02 '15 at 13:31
@moooeeeep Yes, it works for all non-international e-mail addresses — FrozenHeart, Dec 02 '15 at 13:33
@Iron Fist It doesn't work anyway -- `{'Name <\xc3\xb1o\xc3\xb1\xc3\xb31234@server.com>': (555, '5.5.2 Syntax error. i13sm509119lfe.9 - gsmtp')}` — FrozenHeart, Dec 02 '15 at 13:35
@Iron Fist It doesn't work either -- `{'Name <\xf1o\xf1\xf31234@server.com>': (555, '5.5.2 Syntax error. zc2sm494772lbb.40 - gsmtp')}` — FrozenHeart, Dec 02 '15 at 13:49
Internationalized addresses are a special use case for which according to RFC 6530, server should announce a SMTPUTF8 capability, and client passes SMTPUTF8 option in its `MAIL` command. Python smtplib **can** pass SMTPUTF8 option if the server announces it and if programmer asks for. You should add `server.set_debuglevel(7)` immediatley after `server = smtplib.SMTP(smtp_server)` and report here the session transcript. — Serge Ballesta, Dec 02 '15 at 14:40
@Serge Ballesta http://pastie.org/10598547. It seems that `smtplib` doesn't send this command to the server — FrozenHeart, Dec 02 '15 at 14:59

score 3 · Accepted Answer · edited Oct 07 '21 at 08:58

RFC 6533 - Overview and Framework for Internationalized Email states that server side:

An SMTP relay MUST

Either recognize the format explicitly, agreeing to do so via an ESMTP option, or

Reject the message or, if necessary, return a non-delivery notification message, so that the sender can make another plan.

And RFC 6531 - SMTP Extension for Internationalized Email says as precisions (extracts):

The EHLO keyword value associated with this extension is "SMTPUTF8"

One OPTIONAL parameter, SMTPUTF8, is added to the MAIL command.

If the envelope or message being sent requires the capabilities of the SMTPUTF8 extension, the SMTPUTF8-aware SMTP client MUST supply the SMTPUTF8 parameter with the MAIL command.

As the trace of the exchange with GMail SMTP server proves that it announces itself as a SMTPUTF8 compliant server, you just have to ask smtplib to give the SMTPUTF8 option in mail command. You only need to change the sendmail command to:

server.sendmail(from_email, to_email.encode('utf-8'), msg.as_string(), ['SMTPUTF8'])

As you already process eventual non ASCII characters in body and set appropriate headers with MIMEMultipart and MIMEText all should be Ok.

How to send an e-mail to the international address

1 Answers1