Joseph Harris created AIRFLOW-835:
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             Summary: SMTP Mail delivery fails with server using CRAM-MD5 auth
                 Key: AIRFLOW-835
                 URL: https://issues.apache.org/jira/browse/AIRFLOW-835
             Project: Apache Airflow
          Issue Type: Bug
          Components: utils
    Affects Versions: Airflow 1.7.1
         Environment: https://hub.docker.com/_/python/ (debian:jessie + 
python2.7 in docker)
            Reporter: Joseph Harris
            Priority: Minor


Traceback when sending email from smtp-server configured to offer CRAM-MD5 (in 
all cases, tls included). This occurs because the configuration module returns 
the password as a futures.types.newstr, instead of a plain str (see below for 
gory details of why this breaks).

Traceback (most recent call last):
  File "/usr/local/lib/python2.7/site-packages/airflow/models.py", line 1308, 
in handle_failure
    self.email_alert(error, is_retry=False)
  File "/usr/local/lib/python2.7/site-packages/airflow/models.py", line 1425, 
in email_alert
    send_email(task.email, title, body)
  File "/usr/local/lib/python2.7/site-packages/airflow/utils/email.py", line 
43, in send_email
    return backend(to, subject, html_content, files=files, dryrun=dryrun)
  File "/usr/local/lib/python2.7/site-packages/airflow/utils/email.py", line 
79, in send_email_smtp
    send_MIME_email(SMTP_MAIL_FROM, to, msg, dryrun)
  File "/usr/local/lib/python2.7/site-packages/airflow/utils/email.py", line 
95, in send_MIME_email
    s.login(SMTP_USER, SMTP_PASSWORD)
  File "/usr/local/lib/python2.7/smtplib.py", line 607, in login
    (code, resp) = self.docmd(encode_cram_md5(resp, user, password))
  File "/usr/local/lib/python2.7/smtplib.py", line 571, in encode_cram_md5
    response = user + " " + hmac.HMAC(password, challenge).hexdigest()
  File "/usr/local/lib/python2.7/hmac.py", line 75, in __init__
    self.outer.update(key.translate(trans_5C))
  File "/usr/local/lib/python2.7/site-packages/future/types/newstr.py", line 
390, in translate
    if ord(c) in table:
TypeError: 'in <string>' requires string as left operand, not int

SMTP configs:

[email]
email_backend = airflow.utils.email.send_email_smtp

[smtp]
smtp_host = {a_smtp_server}
smtp_port = 587
smtp_starttls = True
smtp_ssl = False
smtp_user = {a_username}
smtp_password = {a_password}
smtp_mail_from = {a_email_addr}


*Gory details
If the server offers CRAM-MD5, smptlib prefers this by default, and will try to 
use hmac.HMAC to hash the password:
https://hg.python.org/cpython/file/2.7/Lib/smtplib.py#l602
https://hg.python.org/cpython/file/2.7/Lib/smtplib.py#l571

But if the password is a newstr, newstr.translate expects a dict mapping 
instead of str, and raises an exception.
https://hg.python.org/cpython/file/2.7/Lib/hmac.py#l75

All of this occurs after a successful SMTP.ehlo(), so it's probably not crap 
container networking


Could be resolved by passing the smtp password as a futures.types.newbytes, as 
this behaves as expected:

from future.types import newstr, newbytes
import hmac

# Make str / newstr types
test = 'a_string'
test_newstr = newstr(test)
test_newbytes = newbytes(test)

msg = 'future problems'

# Test 1 - Try to do a HMAC:
# fine
hmac.HMAC(test, msg)

# fails horribly
hmac.HMAC(test_newstr, msg)

# is completely fine
hmac.HMAC(test_newbytes, msg)



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