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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