andreh998 opened a new issue, #55953:
URL: https://github.com/apache/airflow/issues/55953
### Apache Airflow version
3.0.6
### If "Other Airflow 2 version" selected, which one?
3.0.6 (also reproduced in 3.1.0rc1)
### What happened?
I am configuring Airflow to send emails when a task fails. When configuring
SMTP email settings via [smtp] section in airflow.cfg or via environment
variables (AIRFLOW__SMTP__SMTP_*), Airflow fails to authenticate against Gmail
SMTP. I even created a test DAG that fails on purpose just to trigger the
email, and it consistently shows the same issue.
My airflow.cfg:
> [email]
> email_backend = airflow.utils.email.send_email_smtp
> subject_template = /opt/airflow/config/my_subject_template_file.txt
> html_content_template =
/opt/airflow/config/my_html_content_template_file.html
> from_email = **@****.com.br
>
> [smtp]
> smtp_host = smtp.gmail.com
> smtp_starttls = True
> smtp_ssl = False
> smtp_port = 587
> smtp_user = test@****.com.br
> smtp_mail_from = ***@****.com.br
> # smtp_password = password_here # i try put the password here to
my docker-compose.yaml
> AIRFLOW__SMTP__SMTP_PASSWORD: 'password_here' # password SMTP
I created a test DAG that fails on purpose just to send the email:
```
import pendulum
from airflow.decorators import task, dag
@dag(
dag_id="email_test_dag",
start_date=pendulum.datetime(2025, 9, 1, tz="UTC"),
schedule=None,
catchup=False,
tags=["test", "email"],
default_args={
'owner': 'airflow',
'email_on_failure': True,
'email_on_retry': False,
'email': ['andre.hoffmann@****.com.br',],
}
)
def email_test_dag():
@task
def raise_error_and_send_email():
raise ValueError("Test email")
raise_error_and_send_email()
email_test_dag_instance = email_test_dag()
```
I can retrieve the information from both airflow.cfg and the environment
using the commands below, in both the worker and the scheduler containers.:
```
airflow@3ff76e0d829c:/opt/airflow$ airflow config get-value smtp smtp_user
****@*****.com.br
airflow@3ff76e0d829c:/opt/airflow$ airflow config get-value smtp
smtp_password
password_here
```
But after running the DAG I get the following errors:
```
Log message source details:
sources=["/opt/airflow/logs/dag_id=email_test_dag/run_id=manual__2025-09-22T12:13:57.617716+00:00/task_id=raise_error_and_send_email/attempt=1.log"]
[2025-09-22, 09:14:08] INFO - DAG bundles loaded: dags-folder:
source="airflow.dag_processing.bundles.manager.DagBundlesManager"
[2025-09-22, 09:14:08] INFO - Filling up the DagBag from
/opt/airflow/dags/email_test_dag.py: source="airflow.models.dagbag.DagBag"
[2025-09-22, 09:14:08] ERROR - Task failed with exception: source="task"
ValueError: Teste de falha de e-mail do Airflow!
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/execution_time/task_runner.py",
line 920 in run
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/execution_time/task_runner.py",
line 1215 in _execute_task
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/bases/operator.py",
line 397 in wrapper
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/bases/decorator.py",
line 251 in execute
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/bases/operator.py",
line 397 in wrapper
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/providers/standard/operators/python.py",
line 216 in execute
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/providers/standard/operators/python.py",
line 239 in execute_callable
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/execution_time/callback_runner.py",
line 81 in run
File "/opt/airflow/dags/email_test_dag.py", line 27 in
raise_error_and_send_email
[2025-09-22, 09:14:08] WARNING -
/home/airflow/.local/lib/python3.12/site-packages/airflow/models/connection.py:471:
DeprecationWarning: Using Connection.get_connection_from_secrets from
`airflow.models` is deprecated.Please use `get` on Connection from
sdk(`airflow.sdk.Connection`) instead
warnings.warn(
: source="py.warnings"
[2025-09-22, 09:14:08] INFO - Email alerting: attempt 1:
source="airflow.utils.email"
[2025-09-22, 09:14:09] INFO - Sent an alert email to
['andre.hoffmann@****.com.br', 'augusto.hagemeier@****.com.br']:
source="airflow.utils.email"
[2025-09-22, 09:14:10] INFO - Email alerting: attempt 1:
source="airflow.utils.email"
[2025-09-22, 09:14:10] INFO - Sent an alert email to
['andre.hoffmann@****.com.br', 'augusto.hagemeier@****.com.br']:
source="airflow.utils.email"
[2025-09-22, 09:14:11] ERROR - Top level error: source="task"
SMTPSenderRefused: (530, b'5.7.0 Authentication Required. For more
information, go to\n5.7.0
https://support.google.com/accounts/troubleshooter/2402620.
d9443c01a7336-2698030ee20sm131927125ad.109 - gsmtp', '***@****.com.br')
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/execution_time/task_runner.py",
line 1353 in main
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/execution_time/task_runner.py",
line 1330 in finalize
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/execution_time/task_runner.py",
line 1165 in _send_task_error_email
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/utils/email.py",
line 79 in send_email
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/utils/email.py",
line 154 in send_email_smtp
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/utils/email.py",
line 273 in send_mime_email
File "/usr/local/lib/python3.12/smtplib.py", line 876 in sendmail
SMTPSenderRefused: (530, b'5.7.0 Authentication Required. For more
information, go to\n5.7.0
https://support.google.com/accounts/troubleshooter/2402620.
d9443c01a7336-269802de979sm132468545ad.69 - gsmtp', '***@****.com.br')
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/execution_time/task_runner.py",
line 1163 in _send_task_error_email
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/utils/email.py",
line 79 in send_email
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/utils/email.py",
line 154 in send_email_smtp
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/utils/email.py",
line 273 in send_mime_email
File "/usr/local/lib/python3.12/smtplib.py", line 876 in sendmail
[2025-09-22, 09:14:11] WARNING - Process exited abnormally: exit_code=1:
source="task"
```
tried switching between ports 587 and 465, between SSL and TLS, and I also
tried adding all the configurations from airflow.cfg into docker-compose.yaml
as environment variables, but the error persisted.
Even when testing via Python and importing send_email_smtp, I was not able
to succeed:
```
>>> from airflow.utils.email import send_email_smtp
>>> send_email_smtp( ... to="andre.hoffmann@****.com.br", subject="Test SMTP
Airflow", html_content="Test")
[2025-09-22T11:52:58.491+0000] {email.py:261} INFO - Email alerting: attempt
1
[2025-09-22T11:52:59.304+0000] {email.py:272} INFO - Sent an alert email to
['andre.hoffmann@****.com.br']
Traceback (most recent call last):
File "<stdin>", line 1, in <module>
File
"/home/airflow/.local/lib/python3.12/site-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
"/home/airflow/.local/lib/python3.12/site-packages/airflow/utils/email.py",
line 273, in send_mime_email smtp_conn.sendmail(e_from, e_to,
mime_msg.as_string()) File "/usr/local/lib/python3.12/smtplib.py", line 876, in
sendmail raise SMTPSenderRefused(code, resp, from_addr)
smtplib.SMTPSenderRefused: (530, b'5.7.0 Authentication Required. For more
information, go to\n5.7.0
https://support.google.com/accounts/troubleshooter/2402620.
d9443c01a7336-26980053201sm131546055ad.17 - gsmtp', '***@****.com.br')
>>>
```
Only after defining a default SMTP connection in the environment variables,
it worked:
> AIRFLOW_CONN_SMTP_DEFAULT:
"smtp://***%40****.com.br:[email protected]:587?secure=starttls"
Airflow task test:
```
Log message source details:
sources=["/opt/airflow/logs/dag_id=email_test_dag/run_id=manual__2025-09-22T13:09:36.683154+00:00/task_id=raise_error_and_send_email/attempt=1.log"]
::group::Log message source details:
sources=["/opt/airflow/logs/dag_id=email_test_dag/run_id=manual__2025-09-22T13:09:36.683154+00:00/task_id=raise_error_and_send_email/attempt=1.log"]
[2025-09-22, 10:09:51] INFO - DAG bundles loaded: dags-folder:
source="airflow.dag_processing.bundles.manager.DagBundlesManager"
[2025-09-22, 10:09:51] INFO - Filling up the DagBag from
/opt/airflow/dags/email_test_dag.py: source="airflow.models.dagbag.DagBag"
[2025-09-22, 10:09:51] ERROR - Task failed with exception: source="task"
ValueError: Teste de falha de e-mail do Airflow!
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/execution_time/task_runner.py",
line 920 in run
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/execution_time/task_runner.py",
line 1215 in _execute_task
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/bases/operator.py",
line 397 in wrapper
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/bases/decorator.py",
line 251 in execute
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/bases/operator.py",
line 397 in wrapper
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/providers/standard/operators/python.py",
line 216 in execute
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/providers/standard/operators/python.py",
line 239 in execute_callable
File
"/home/airflow/.local/lib/python3.12/site-packages/airflow/sdk/execution_time/callback_runner.py",
line 81 in run
File "/opt/airflow/dags/email_test_dag.py", line 27 in
raise_error_and_send_email
[2025-09-22, 10:09:52] WARNING -
/home/airflow/.local/lib/python3.12/site-packages/airflow/models/connection.py:471:
DeprecationWarning: Using Connection.get_connection_from_secrets from
`airflow.models` is deprecated.Please use `get` on Connection from
sdk(`airflow.sdk.Connection`) instead
warnings.warn(
: source="py.warnings"
[2025-09-22, 10:09:52] WARNING - empty cryptography key - values will not be
stored encrypted.: source="airflow.models.crypto"
[2025-09-22, 10:09:52] INFO - Connection Retrieved 'smtp_default':
source="airflow.hooks.base"
[2025-09-22, 10:09:52] INFO - Email alerting: attempt 1:
source="airflow.utils.email"
[2025-09-22, 10:09:53] INFO - Sent an alert email to
['andre.hoffmann@****.com.br']: source="airflow.utils.email"
```
### What you think should happen instead?
It should work just by setting the environment variables or the airflow.cfg.
### How to reproduce
By filling in the SMTP information in the airflow.cfg and/or in the .env
file and running a task that fails.
### Operating System
apache/airflow:3.1.0rc1
### Versions of Apache Airflow Providers
_No response_
### Deployment
Docker-Compose
### Deployment details
_No response_
### 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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