Can you enable debug logging for Alertmanager? That should show whether it
is even trying to send an email.

How does SendGrid behave when you submit something with invalid
credentials? Do you expect that to explicitly fail?

>From this doc
<https://sendgrid.com/docs/API_Reference/SMTP_API/getting_started_smtp.html>,
SendGrid seems to use LOGIN not PLAIN. Try leaving out `smtp_auth_identity`
and only specifying user and password?

/MR


On Sat, Jun 13, 2020 at 8:14 PM Cristhian Rivera <[email protected]>
wrote:

> Hi I'm trying to send the alerts generated by Prometheus trough the
> SendGrid SMTP.
>
> Following the SendGrid docs:
> https://sendgrid.com/docs/API_Reference/SMTP_API/integrating_with_the_smtp_api.html
>
> I included the corresponding settings:
>
> global:
>   smtp_from: "AlertManager <[email protected]>"
>   smtp_smarthost: smtp.sendgrid.net:587
>   smtp_require_tls: true
>   smtp_auth_username: apikey
>   smtp_auth_identity: apikey
>   smtp_auth_password: "<MY API KEY>"
>
> route:
>   repeat_interval: 1m
>   receiver: default
>
> receivers:
>   - name: default
>     email_configs:
>       - to: [email protected]
>
> Then with a current alert active in prometheus I'm not receiving any
> emails. And in the SendGrid dashboard there is no activity either.
>
> Also in the logs of the container there is no indication that there is an
> issue:
>
> level=info ts=2020-06-13T20:03:47.844Z caller=main.go:231 msg="Starting 
> Alertmanager" version="(version=0.20.0, branch=HEAD, 
> revision=f74be0400a6243d10bb53812d6fa408ad71ff32d)"
>
>
> level=info ts=2020-06-13T20:03:47.844Z caller=main.go:232 
> build_context="(go=go1.13.5, user=root@00c3106655f8, date=20191211-14:13:14)"
>
>
> level=info ts=2020-06-13T20:03:47.845Z caller=cluster.go:161 
> component=cluster msg="setting advertise address explicitly" addr=172.19.0.4 
> port=9094
>
>
> level=info ts=2020-06-13T20:03:47.846Z caller=cluster.go:623 
> component=cluster msg="Waiting for gossip to settle..." interval=2s
>
>
> level=info ts=2020-06-13T20:03:47.872Z caller=coordinator.go:119 
> component=configuration msg="Loading configuration file" 
> file=/etc/alertmanager/alert-manager.yaml
>
>
> level=info ts=2020-06-13T20:03:47.872Z caller=coordinator.go:131 
> component=configuration msg="Completed loading of configuration file" 
> file=/etc/alertmanager/alert-manager.yaml
>
>
> level=info ts=2020-06-13T20:03:47.874Z caller=main.go:497 msg=Listening 
> address=:9093
>
>
> level=info ts=2020-06-13T20:03:49.848Z caller=cluster.go:648 
> component=cluster msg="gossip not settled" polls=0 before=0 now=1 
> elapsed=2.001599783s
>
>
> level=info ts=2020-06-13T20:03:57.857Z caller=cluster.go:640 
> component=cluster msg="gossip settled; proceeding" elapsed=10.010722253s
>
>
> I've tried with the other ports that SendGrid supports but the same result
>
> Only when the port is 25 and the smtp_require_tls: is set to false I
> receive a warning of
>
> level=error ts=2020-06-13T20:13:33.862Z caller=dispatch.go:301 
> component=dispatcher msg="Notify for alerts failed" num_alerts=1 
> err="*smtp.plainAuth auth: unencrypted connection"
>
>
> Any idea of what I'm missing here?
>
> Thanks!
>
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