Hi Bryan,

Rather, am I correct to say that it is *Prometheus that does not support
OAuth2 based authentication for SMTP email *configuration. I followed this
post for smpt_config. But despite giving the access_token the SMTP server
gives an error as below:

err="email-alert/email[0]: notify retry canceled after 4 attempts:
*email.loginAuth auth: 535 5.7.139 Authentication unsuccessful,* basic
authentication is disabled.* [MA0****0074.INDPRD01.PROD.OUTLOOK.COM
2025-05-09T07:00:20.974Z ********]"

It seems that despite providing the access_token the SMTP server is *confusing
it as a basic authentication*. (?)

global:
  smtp_smarthost: 'smtp.office365.com:587'
  smtp_from: '[email protected]'
  *smtp_auth_username*: '[email protected]'
  smtp_auth_password: 'YOUR_ACCESS_TOKEN'
  smtp_require_tls: true

Regards,
Dipak.


On Thu, May 8, 2025 at 9:11 PM Bryan Boreham <[email protected]> wrote:

> You have added a token under http_config, but mail sending uses smtp not
> http.
>
> There are a few settings like smtp_auth_secret, but I have no idea whether
> Microsoft will accept them.
>
> Bryan
>
> On Thursday, 8 May 2025 at 16:37:00 UTC+1 [email protected] wrote:
>
>> Snippet of my alertmanager.yml file:
>>
>>     global:
>>       smtp_smarthost: "smtp.office365.com:587"
>>       smtp_from: "[email protected]"
>>       http_config:
>>        oauth2:
>>          client_id: "76214c65-6283-4368-abbe-987********"
>>          client_secret: "Vp_8Q~********~97~*********~b~D"
>>          token_url: "
>> https://login.microsoftonline.com/5d471751-917b-********/oauth2/v2.0/token
>> "
>>          scopes: ["https://outlook.office365.com/.default";]
>>          tls_config:
>>            insecure_skip_verify: true
>>          endpoint_params:
>>             grant_type: "client_credentials"
>>
>> But as I load the alert manager and wait for the emails being sent I get
>> the below error:
>>
>>  time=2025-05-08T15:16:47.536Z level=ERROR source=dispatch.go:360
>>  msg="Notify for alerts failed" component=dispatcher num_alerts=1
>>  err="email-alert/email[0]: notify retry canceled after 7 attempts:
>>  send MAIL command: 530 5.7.57 *Client not authenticated to send mail.*
>>  [*****.INDP287.***.OUTLOOK.COM 2025-05-08T15:16:42.409Z.****]"
>>
>> What is wrong with my configuration in prometheus? I have duly followed
>> the links here
>>
>>    -
>>    
>> https://prometheus.io/docs/prometheus/latest/configuration/configuration/#oauth2
>>    -
>>    
>> https://learn.microsoft.com/en-us/exchange/client-developer/legacy-protocols/how-to-authenticate-an-imap-pop-smtp-application-by-using-oauth
>>
>>
>>
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