The error "dial tcp 74.125.206.108:587: i/o timeout" suggests that your 
container can't even make an outbound network connection. Try logging into 
the container and running "telnet smtp.gmail.com 587" or "nc 
smtp.gmail.com:587".  You should get a banner back like this:

220 smtp.gmail.com ESMTP t26-2002.............1 - gsmtp

If you don't, then you have a networking/firewalling issue to investigate 
on your k8s cluster - it's nothing to do with alertmanager.

As for your config, I observe that your 'receivers' section doesn't look 
like what Alertmanager requires:
https://prometheus.io/docs/alerting/latest/configuration/#email_config
For example, you have "emailConfigs" whereas alertmanager requires 
"email_configs".

Presumably, therefore, you are using some middleware which is munging the 
config before giving it to alertmanager (I guess this is something provided 
by "monitoring.coreos.com"?)

If you're able to find the alertmanager config *as deployed* by this 
middleware, e.g. by entering the running container and printing it, then 
you can post that here - or it may be obvious what the problem is. Note 
that auth_password is *not* base64 encoded in the alertmanager config file 
- I don't know if your middleware base64-decodes it as part of deployment.

On Sunday, 30 April 2023 at 09:12:20 UTC+1 Zikou wrote:

> I'm testing to trigger alert manager to send email but It doesnt work logs 
> that I got from the pod of alert manager
>
> ts=2023-04-18T17:35:15.453Z caller=dispatch.go:352 level=error 
> component=dispatcher msg="Notify for alerts failed" num_alerts=1 
> err="monitoring/main-rules-alert-config/email/email[0]: notify retry 
> canceled after 4 attempts: establish connection to server: dial tcp 
> 74.125.206.108:587: i/o timeout"
> and here is the content of my alertmanagerconfig
>
> apiVersion: monitoring.coreos.com/v1alpha1
> kind: AlertmanagerConfig
> metadata:
>   name: main-rules-alert-config
>   namespace: monitoring
> spec:
>   route:
>     receiver: 'email'
>     repeatInterval: 30m
>     routes:
>     - matchers:
>       - name: alertname
>         value: HostHighCPULoad
>     - matchers:
>       - name: alertname
>         value: KuberenetesPodCrashLooping
>       repeatInterval: 30m
>   receivers:
>     - name: 'email'
>       emailConfigs:
>       - to: "zikou...@gmail.com"
>         from: "zikou...@gmail.com"
>         smarthost: 'smtp.gmail.com:587'
>         authIdentity: "zikou...@gmail.com"
>         authUsername: "zikou...@gmail.com"
>         authPassword:
>           name: gmail-auth
>           key: password
> I created a secret named gmail-auth (in the same namespace as alert) 
> before apply the alert config the secret contain password of my gmail but 
> since 2FA is enabled I put app passwors in the secret base64 of course but 
> I dont know where is the issue why I dont receive any mail
>

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