winmasta opened a new issue, #39644:
URL: https://github.com/apache/airflow/issues/39644

   ### Apache Airflow version
   
   2.9.1
   
   ### If "Other Airflow 2 version" selected, which one?
   
   _No response_
   
   ### What happened?
   
   I am trying to use EmailOperator to sent email via SMTP server, but there is 
error
   
   <details>
   <summary>Traceback</summary>
   `
   airflow.ru-central1.internal
   *** Found local files:
   ***   * 
/root/airflow/logs/dag_id=email/run_id=manual__2024-05-15T15:41:41.857115+00:00/task_id=email/attempt=1.log
   [2024-05-15, 22:41:43 +07] {local_task_job_runner.py:120} ▼ Pre task 
execution logs
   [2024-05-15, 22:41:43 +07] {taskinstance.py:2076} INFO - Dependencies all 
met for dep_context=non-requeueable deps ti=<TaskInstance: email.email 
manual__2024-05-15T15:41:41.857115+00:00 [queued]>
   [2024-05-15, 22:41:43 +07] {taskinstance.py:2076} INFO - Dependencies all 
met for dep_context=requeueable deps ti=<TaskInstance: email.email 
manual__2024-05-15T15:41:41.857115+00:00 [queued]>
   [2024-05-15, 22:41:43 +07] {taskinstance.py:2306} INFO - Starting attempt 1 
of 1
   [2024-05-15, 22:41:43 +07] {taskinstance.py:2330} INFO - Executing 
<Task(EmailOperator): email> on 2024-05-15 15:41:41.857115+00:00
   [2024-05-15, 22:41:43 +07] {standard_task_runner.py:90} INFO - Running: 
['airflow', 'tasks', 'run', 'email', 'email', 
'manual__2024-05-15T15:41:41.857115+00:00', '--job-id', '33', '--raw', 
'--subdir', 'DAGS_FOLDER/test_email.py', '--cfg-path', '/tmp/tmp_576qvon']
   [2024-05-15, 22:41:43 +07] {standard_task_runner.py:91} INFO - Job 33: 
Subtask email
   [2024-05-15, 22:41:43 +07] {logging_mixin.py:188} WARNING - 
/usr/local/lib/python3.12/dist-packages/airflow/task/task_runner/standard_task_runner.py:61
 DeprecationWarning: This process (pid=65487) is multi-threaded, use of fork() 
may lead to deadlocks in the child.
   [2024-05-15, 22:41:43 +07] {standard_task_runner.py:63} INFO - Started 
process 65493 to run task
   [2024-05-15, 22:41:43 +07] {task_command.py:426} INFO - Running 
<TaskInstance: email.email manual__2024-05-15T15:41:41.857115+00:00 [running]> 
on host airflow.ru-central1.internal
   [2024-05-15, 22:41:43 +07] {taskinstance.py:2648} INFO - Exporting env vars: 
AIRFLOW_CTX_DAG_EMAIL='[email protected]' AIRFLOW_CTX_DAG_OWNER='winmasta' 
AIRFLOW_CTX_DAG_ID='email' AIRFLOW_CTX_TASK_ID='email' 
AIRFLOW_CTX_EXECUTION_DATE='2024-05-15T15:41:41.857115+00:00' 
AIRFLOW_CTX_TRY_NUMBER='1' 
AIRFLOW_CTX_DAG_RUN_ID='manual__2024-05-15T15:41:41.857115+00:00'
   [2024-05-15, 22:41:43 +07] {taskinstance.py:430} ▲▲▲ Log group end
   [2024-05-15, 22:41:43 +07] {logging_mixin.py:188} WARNING - 
/usr/local/lib/python3.12/dist-packages/airflow/utils/email.py:154 
RemovedInAirflow3Warning: Fetching SMTP credentials from configuration 
variables will be deprecated in a future release. Please set credentials using 
a connection instead.
   [2024-05-15, 22:41:43 +07] {email.py:271} INFO - Email alerting: attempt 1
   [2024-05-15, 22:41:43 +07] {taskinstance.py:441} ▼ Post task execution logs
   [2024-05-15, 22:41:43 +07] {taskinstance.py:2905} ERROR - Task failed with 
exception
   Traceback (most recent call last):
     File 
"/usr/local/lib/python3.12/dist-packages/airflow/models/taskinstance.py", line 
465, in _execute_task
       result = _execute_callable(context=context, **execute_callable_kwargs)
                ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
     File 
"/usr/local/lib/python3.12/dist-packages/airflow/models/taskinstance.py", line 
432, in _execute_callable
       return execute_callable(context=context, **execute_callable_kwargs)
              ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
     File 
"/usr/local/lib/python3.12/dist-packages/airflow/models/baseoperator.py", line 
400, in wrapper
       return func(self, *args, **kwargs)
              ^^^^^^^^^^^^^^^^^^^^^^^^^^^
     File "/usr/local/lib/python3.12/dist-packages/airflow/operators/email.py", 
line 79, in execute
       send_email(
     File "/usr/local/lib/python3.12/dist-packages/airflow/utils/email.py", 
line 80, in send_email
       return backend(
              ^^^^^^^^
     File "/usr/local/lib/python3.12/dist-packages/airflow/utils/email.py", 
line 154, in send_email_smtp
       send_mime_email(e_from=mail_from, e_to=recipients, mime_msg=msg, 
conn_id=conn_id, dryrun=dryrun)
     File "/usr/local/lib/python3.12/dist-packages/airflow/utils/email.py", 
line 279, in send_mime_email
       smtp_conn.starttls()
     File "/usr/lib/python3.12/smtplib.py", line 794, in starttls
       raise SMTPResponseException(resp, reply)
   smtplib.SMTPResponseException: (503, b'5.5.4 Bad sequence of commands. 
StartTls command has been already sent. 1715787703-hfisA7RwLa60')
   [2024-05-15, 22:41:43 +07] {taskinstance.py:1206} INFO - Marking task as 
FAILED. dag_id=email, task_id=email, 
run_id=manual__2024-05-15T15:41:41.857115+00:00, 
execution_date=20240515T154141, start_date=20240515T154143, 
end_date=20240515T154143
   [2024-05-15, 22:41:43 +07] {email.py:271} INFO - Email alerting: attempt 1
   [2024-05-15, 22:41:43 +07] {email.py:271} INFO - Email alerting: attempt 1
   [2024-05-15, 22:41:43 +07] {taskinstance.py:879} ERROR - Failed to send 
email to: ['[email protected]']
   Traceback (most recent call last):
     File 
"/usr/local/lib/python3.12/dist-packages/airflow/models/taskinstance.py", line 
2479, in _run_raw_task
       self._execute_task_with_callbacks(context, test_mode, session=session)
     File 
"/usr/local/lib/python3.12/dist-packages/airflow/models/taskinstance.py", line 
2676, in _execute_task_with_callbacks
       result = self._execute_task(context, task_orig)
                ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
     File 
"/usr/local/lib/python3.12/dist-packages/airflow/models/taskinstance.py", line 
2701, in _execute_task
       return _execute_task(self, context, task_orig)
              ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
     File 
"/usr/local/lib/python3.12/dist-packages/airflow/models/taskinstance.py", line 
465, in _execute_task
       result = _execute_callable(context=context, **execute_callable_kwargs)
                ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
     File 
"/usr/local/lib/python3.12/dist-packages/airflow/models/taskinstance.py", line 
432, in _execute_callable
       return execute_callable(context=context, **execute_callable_kwargs)
              ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
     File 
"/usr/local/lib/python3.12/dist-packages/airflow/models/baseoperator.py", line 
400, in wrapper
       return func(self, *args, **kwargs)
              ^^^^^^^^^^^^^^^^^^^^^^^^^^^
     File "/usr/local/lib/python3.12/dist-packages/airflow/operators/email.py", 
line 79, in execute
       send_email(
     File "/usr/local/lib/python3.12/dist-packages/airflow/utils/email.py", 
line 80, in send_email
       return backend(
              ^^^^^^^^
     File "/usr/local/lib/python3.12/dist-packages/airflow/utils/email.py", 
line 154, in send_email_smtp
       send_mime_email(e_from=mail_from, e_to=recipients, mime_msg=msg, 
conn_id=conn_id, dryrun=dryrun)
     File "/usr/local/lib/python3.12/dist-packages/airflow/utils/email.py", 
line 279, in send_mime_email
       smtp_conn.starttls()
     File "/usr/lib/python3.12/smtplib.py", line 794, in starttls
       raise SMTPResponseException(resp, reply)
   smtplib.SMTPResponseException: (503, b'5.5.4 Bad sequence of commands. 
StartTls command has been already sent. 1715787703-hfisA7RwLa60')
   During handling of the above exception, another exception occurred:
   Traceback (most recent call last):
     File 
"/usr/local/lib/python3.12/dist-packages/airflow/models/taskinstance.py", line 
1063, in _email_alert
       send_email(task.email, subject, html_content)
     File "/usr/local/lib/python3.12/dist-packages/airflow/utils/email.py", 
line 80, in send_email
       return backend(
              ^^^^^^^^
     File "/usr/local/lib/python3.12/dist-packages/airflow/utils/email.py", 
line 154, in send_email_smtp
       send_mime_email(e_from=mail_from, e_to=recipients, mime_msg=msg, 
conn_id=conn_id, dryrun=dryrun)
     File "/usr/local/lib/python3.12/dist-packages/airflow/utils/email.py", 
line 279, in send_mime_email
       smtp_conn.starttls()
     File "/usr/lib/python3.12/smtplib.py", line 794, in starttls
       raise SMTPResponseException(resp, reply)
   smtplib.SMTPResponseException: (503, b'5.5.4 Bad sequence of commands. 
StartTls command has been already sent. 1715787703-hfiB1pU1RW20')
   During handling of the above exception, another exception occurred:
   Traceback (most recent call last):
     File 
"/usr/local/lib/python3.12/dist-packages/airflow/models/taskinstance.py", line 
877, in _handle_failure
       task_instance.email_alert(error, failure_context["task"])
     File 
"/usr/local/lib/python3.12/dist-packages/airflow/models/taskinstance.py", line 
3163, in email_alert
       _email_alert(task_instance=self, exception=exception, task=task)
     File 
"/usr/local/lib/python3.12/dist-packages/airflow/models/taskinstance.py", line 
1065, in _email_alert
       send_email(task.email, subject, html_content_err)
     File "/usr/local/lib/python3.12/dist-packages/airflow/utils/email.py", 
line 80, in send_email
       return backend(
              ^^^^^^^^
     File "/usr/local/lib/python3.12/dist-packages/airflow/utils/email.py", 
line 154, in send_email_smtp
       send_mime_email(e_from=mail_from, e_to=recipients, mime_msg=msg, 
conn_id=conn_id, dryrun=dryrun)
     File "/usr/local/lib/python3.12/dist-packages/airflow/utils/email.py", 
line 279, in send_mime_email
       smtp_conn.starttls()
     File "/usr/lib/python3.12/smtplib.py", line 794, in starttls
       raise SMTPResponseException(resp, reply)
   smtplib.SMTPResponseException: (503, b'5.5.4 Bad sequence of commands. 
StartTls command has been already sent. 1715787703-hfiTdC0oC0U0')
   [2024-05-15, 22:41:43 +07] {standard_task_runner.py:110} ERROR - Failed to 
execute job 33 for task email ((503, b'5.5.4 Bad sequence of commands. StartTls 
command has been already sent. 1715787703-hfisA7RwLa60'); 65493)
   [2024-05-15, 22:41:43 +07] {local_task_job_runner.py:240} INFO - Task exited 
with return code 1
   [2024-05-15, 22:41:43 +07] {taskinstance.py:3498} INFO - 0 downstream tasks 
scheduled from follow-on schedule check
   [2024-05-15, 22:41:43 +07] {local_task_job_runner.py:222} ▲▲▲ Log group end
   `
   </details>
   
   
   but `smtp_starttls` is `false` in `airflow.cfg`
   
   `# airflow confif list`
   
   [smtp]
   smtp_host = smtp.yandex.ru
   smtp_starttls = false
   smtp_ssl = true
   smtp_user = [email protected]
   smtp_password = ********************
   smtp_port = 465
   smtp_mail_from = [email protected]
   smtp_timeout = 30
   smtp_retry_limit = 5
   
   
   ### What you think should happen instead?
   
   It is supposed to have value from config in `airflow/utils/email.py` 278
   
   ```
   278 if smtp_starttls:
   279    smtp_conn.starttls()
   ```
   
   and not to try to use starttls
   
   ### How to reproduce
   
   Try to use EmailOperator with `smtp_starttls = false` in `airflow.cfg`
   
   ### Operating System
   
   Ubuntu 22.04.4 LTS
   
   ### Versions of Apache Airflow Providers
   
   _No response_
   
   ### Deployment
   
   Other
   
   ### Deployment details
   
   Airflow installed using poetry without virtualenv with python 3.12
   
[requirements.txt](https://github.com/apache/airflow/files/15324082/requirements.txt)
   
   
   ### Anything else?
   
   _No response_
   
   ### Are you willing to submit PR?
   
   - [ ] Yes I am willing to submit a PR!
   
   ### Code of Conduct
   
   - [X] I agree to follow this project's [Code of 
Conduct](https://github.com/apache/airflow/blob/main/CODE_OF_CONDUCT.md)
   


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