You could change the mail server configuration to allow 
PLAIN/LOGIN/CRAM-MD5 like you said, or to allow relaying with no 
authentication from your alertmanager's IP address.  That would be simplest.

Or you could install a local mail server (e.g. postfix), point alertmanager 
at it (localhost:25), and configure it to send all outgoing mail via the 
upstream mailserver with NTLM authentication.

https://www.postfix.org/postconf.5.html#relayhost
https://www.postfix.org/postconf.5.html#smtp_sasl_password_maps
https://www.linuxquestions.org/questions/linux-newbie-8/configure-postfix-to-relay-to-exchange-server-with-ntlm-authentication-4175410961/

On Tuesday 5 November 2024 at 17:28:43 UTC Prabhu ilamathi wrote:

> Hi Brian,
>
> Thanks for your reply and I had identified that my mail server is having 
> NTLM auth type and alert manager is not supporting for NTLM. Do you have 
> any suggestion for this scenario than changing the mail server itself ?
>
> Thanks 
>
> On Tue, 5 Nov 2024 at 6:13 PM, 'Brian Candler' via Prometheus Users <
> [email protected]> wrote:
>
>> What makes you think the problem would be fixed by a proxy - what *exact* 
>> error message are you seeing? And what sort of proxy are you thinking of?
>>
>> If it's an SMTP proxy then you just point alertmanager at it for sending 
>> mails. If it's a SOCKS5 proxy then that functionality is not built-in to 
>> alertmanager, so you'd have to run a standalone proxy that listens on a 
>> port on localhost and makes an outbound TCP connection via the proxy. 
>> (Maybe nc or socat could do that). If it's some other sort of proxy then 
>> you'd have to explain what you mean.
>>
>> It might make more sense to put your alertmanager in a position in the 
>> network where it can make the necessary network connections it needs.
>>
>> On Tuesday 5 November 2024 at 16:30:10 UTC Prabhu ilamathi wrote:
>>
>>> Hi All,
>>>
>>> Right now am using the alertmanager.yml configured to use the smtp 
>>> server details. but am unable to send the emails, so i am thinking proxy 
>>> would be resolving it , could you please help me with some examples on 
>>> implementing the same ?
>>>
>>> Thanks,
>>> Prabhu
>>>
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