Soren Bliefnick created AIRFLOW-6492:
----------------------------------------

             Summary: Automated emails fail because of SSL: unsupported 
protocol error
                 Key: AIRFLOW-6492
                 URL: https://issues.apache.org/jira/browse/AIRFLOW-6492
             Project: Apache Airflow
          Issue Type: Bug
          Components: core
    Affects Versions: 1.10.7
         Environment: Docker container python:3.7-slim
            Reporter: Soren Bliefnick


After upgrading from 1.10.3 to 1.10.7, with SMTP settings and DAGs the same, 
email_on_failure emails and email_operator emails fail to send.

 

In airflow.cfg:
{code:java}
smtp_starttls: True
smtp_ssl: False  # tried with True as well; same result
{code}
 

Error:
{code:java}
[2020-01-06 20:09:35,505] {taskinstance.py:887} INFO - Executing 
<Task(EmailOperator): email_bmt> on 2019-12-30T20:00:00+00:00
[2020-01-06 20:09:35,509] {standard_task_runner.py:52} INFO - Started process 
106 to run task
[2020-01-06 20:09:35,592] {logging_mixin.py:112} INFO - [2020-01-06 
20:09:35,592] {dagbag.py:403} INFO - Filling up the DagBag from 
/var/nfsshare/dags/send_bmt.py
[2020-01-06 20:09:35,804] {logging_mixin.py:112} INFO - Running %s on host %s 
<TaskInstance: send_bmt.email_bmt 2019-12-30T20:00:00+00:00 [running]> 
fd36fd6eafea
[2020-01-06 20:09:36,344] {taskinstance.py:1088} ERROR - [SSL: 
UNSUPPORTED_PROTOCOL] unsupported protocol (_ssl.c:1076)
Traceback (most recent call last):
  File "/usr/local/lib/python3.7/site-packages/airflow/models/taskinstance.py", 
line 955, in _run_raw_task
    result = task_copy.execute(context=context)
  File 
"/usr/local/lib/python3.7/site-packages/airflow/operators/email_operator.py", 
line 78, in execute
    mime_subtype=self.mime_subtype, mime_charset=self.mime_charset)
  File "/usr/local/lib/python3.7/site-packages/airflow/utils/email.py", line 
60, in send_email
    mime_subtype=mime_subtype, mime_charset=mime_charset, **kwargs)
  File "/usr/local/lib/python3.7/site-packages/airflow/utils/email.py", line 
106, in send_email_smtp
    send_MIME_email(smtp_mail_from, recipients, msg, dryrun)
  File "/usr/local/lib/python3.7/site-packages/airflow/utils/email.py", line 
128, in send_MIME_email
    s.starttls()
  File "/usr/local/lib/python3.7/smtplib.py", line 771, in starttls
    server_hostname=self._host)
  File "/usr/local/lib/python3.7/ssl.py", line 423, in wrap_socket
    session=session
  File "/usr/local/lib/python3.7/ssl.py", line 870, in _create
    self.do_handshake()
  File "/usr/local/lib/python3.7/ssl.py", line 1139, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLError: [SSL: UNSUPPORTED_PROTOCOL] unsupported protocol (_ssl.c:1076)
[2020-01-06 20:09:36,347] {taskinstance.py:1117} INFO - All retries failed; 
marking task as FAILED
[2020-01-06 20:09:36,410] {taskinstance.py:1123} ERROR - Failed to send email 
to: ['****@****.org']
[2020-01-06 20:09:36,411] {taskinstance.py:1124} ERROR - [SSL: 
UNSUPPORTED_PROTOCOL] unsupported protocol (_ssl.c:1076)
Traceback (most recent call last):
  File "/usr/local/lib/python3.7/site-packages/airflow/models/taskinstance.py", 
line 955, in _run_raw_task
    result = task_copy.execute(context=context)
  File 
"/usr/local/lib/python3.7/site-packages/airflow/operators/email_operator.py", 
line 78, in execute
    mime_subtype=self.mime_subtype, mime_charset=self.mime_charset)
  File "/usr/local/lib/python3.7/site-packages/airflow/utils/email.py", line 
60, in send_email
    mime_subtype=mime_subtype, mime_charset=mime_charset, **kwargs)
  File "/usr/local/lib/python3.7/site-packages/airflow/utils/email.py", line 
106, in send_email_smtp
    send_MIME_email(smtp_mail_from, recipients, msg, dryrun)
  File "/usr/local/lib/python3.7/site-packages/airflow/utils/email.py", line 
128, in send_MIME_email
    s.starttls()
  File "/usr/local/lib/python3.7/smtplib.py", line 771, in starttls
    server_hostname=self._host)
  File "/usr/local/lib/python3.7/ssl.py", line 423, in wrap_socket
    session=session
  File "/usr/local/lib/python3.7/ssl.py", line 870, in _create
    self.do_handshake()
  File "/usr/local/lib/python3.7/ssl.py", line 1139, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLError: [SSL: UNSUPPORTED_PROTOCOL] unsupported protocol (_ssl.c:1076)

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/usr/local/lib/python3.7/site-packages/airflow/models/taskinstance.py", 
line 1121, in handle_failure
    self.email_alert(error)
  File "/usr/local/lib/python3.7/site-packages/airflow/models/taskinstance.py", 
line 1357, in email_alert
    send_email(self.task.email, subject, html_content)
  File "/usr/local/lib/python3.7/site-packages/airflow/utils/email.py", line 
60, in send_email
    mime_subtype=mime_subtype, mime_charset=mime_charset, **kwargs)
  File "/usr/local/lib/python3.7/site-packages/airflow/utils/email.py", line 
106, in send_email_smtp
    send_MIME_email(smtp_mail_from, recipients, msg, dryrun)
  File "/usr/local/lib/python3.7/site-packages/airflow/utils/email.py", line 
128, in send_MIME_email
    s.starttls()
  File "/usr/local/lib/python3.7/smtplib.py", line 771, in starttls
    server_hostname=self._host)
  File "/usr/local/lib/python3.7/ssl.py", line 423, in wrap_socket
    session=session
  File "/usr/local/lib/python3.7/ssl.py", line 870, in _create
    self.do_handshake()
  File "/usr/local/lib/python3.7/ssl.py", line 1139, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLError: [SSL: UNSUPPORTED_PROTOCOL] unsupported protocol (_ssl.c:1076)
[2020-01-06 20:09:45,389] {logging_mixin.py:112} INFO - [2020-01-06 
20:09:45,388] {local_task_job.py:103} INFO - Task exited with return code 1
{code}



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