Looks like you're right. Issue is open here: 
https://github.com/prometheus/alertmanager/issues/3244


On Friday, 9 May 2025 at 08:05:14 UTC+1 [email protected] wrote:

> 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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>>
>

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