SMTP Connection Difficulties

[truthsword]

I'm trying to run a docker instance on RPi which is email notification only. I'm presently trying a "@live.com" email without success. My most recent error message is:

time="2022-07-15T19:25:30-04:00" level=error msg="Failed to send shoutrrr notification" error="error getting SMTP client: error connecting to server: dial tcp :25: connect: connection refused" index=0 notify=no service=smtp

My docker compose is:

version: '3.8'
services:
  watchtower:
    image: containrrr/watchtower
    container_name: watchtower
    restart: unless-stopped
    volumes:
        - /var/run/docker.sock:/var/run/docker.sock
    environment:
        - WATCHTOWER_MONITOR_ONLY=true
        - WATCHTOWER_NOTIFICATIONS=email
        - WATCHTOWER_NOTIFICATION_EMAIL_FROM=abcdefg@live.com
        - WATCHTOWER_NOTIFICATION_EMAIL_TO=qwerty@login.com
        - WATCHTOWER_NOTIFICATION_EMAIL_SERVER:smtp-mail.outlook.com
#        - WATCHTOWER_NOTIFICATION_EMAIL_SERVER_TLS_SKIP_VERIFY=true
        - WATCHTOWER_NOTIFICATION_EMAIL_SERVER_PORT:587
        - WATCHTOWER_NOTIFICATION_EMAIL_SERVER_USER=abcdefgf@live.com
        - WATCHTOWER_NOTIFICATION_EMAIL_SERVER_PASSWORD=secretpwd
        - WATCHTOWER_NOTIFICATION_EMAIL_SUBJECTTAG:Docker Container Updates
        - WATCHTOWER_SCHEDULE=0 0 5 * * *
        - WATCHTOWER_CLEANUP=true
        - WATCHTOWER_DEBUG=true
        - WATCHTOWER_NOTIFICATION_EMAIL_DELAY=30
        - WATCHTOWER_TIMEOUT=30s
        - WATCHTOWER_NOTIFICATIONS_LEVEL=info
        - TZ=America/Chicago

I've tried '=' and ':' for server and port and had no success either way.

I'd welcome any suggestions.

[piksel]

If you run it with --trace or WATCHTOWER_TRACE=true you can see what e-mail setting URL it constructed:

watchtower  | time="2022-07-16T02:53:11-05:00" level=trace msg="created Shoutrrr URL from legacy notifier" URL="smtp://abcdefgf%40live.com:secretpwd@smtp-mail.outlook.com:587/?auth=Plain&fromaddress=abcdefg%40live.com&fromname=Watchtower&subject=Docker+Container+Updates+Watchtower+updates+on+330fe9182436&toaddresses=qwerty%40login.com"

(this is from your posted docker-compose.yml, but with : separators replaced with =)

But the main problem is that the authentication mode that the outlook mail servers need is not supported by the go smtp library. I would suggest using another mail provider that is better aimed at this type of usage, like Sendgrid or Mailgun.

Ref: #474

[truthsword]

If you run it with --trace or WATCHTOWER_TRACE=true you can see what e-mail setting URL it constructed:

watchtower  | time="2022-07-16T02:53:11-05:00" level=trace msg="created Shoutrrr URL from legacy notifier" URL="smtp://abcdefgf%40live.com:secretpwd@smtp-mail.outlook.com:587/?auth=Plain&fromaddress=abcdefg%40live.com&fromname=Watchtower&subject=Docker+Container+Updates+Watchtower+updates+on+330fe9182436&toaddresses=qwerty%40login.com"

That matches what I see here.

time="2022-07-16T10:49:12-04:00" level=trace msg="created Shoutrrr URL from legacy notifier" URL="smtp://abcdefg%40live.com:secretpwd@smtp-mail.outlook.com:587/?auth=Plain&fromaddress=abcdefg%40live.com&fromname=Watchtower&subject=Watchtower+updates+on+a8c99306c3f6&toaddresses=qwerty@login.com"

Apart from subject line changes. So apparently, this is a mail provider (Microsoft) issue. Unfortunately, I have this similar situation with my ISP's mail server. I hoped not to create a new email account for Watchtower notifications. Gotta think this through. Thanks!

[piksel]

What error message do you get in the logs? It should be something like:

watchtower  | time="2022-07-18T04:00:08-05:00" level=error msg="Failed to send shoutrrr notification" error="failed to send using smtp: timed out"

(the timeout is because the microsoft SMTP servers are really slow to respond when you use the incorrect authentication. probably dos/brute force protection. if the internal timeout is increased, it responds with 504 5.7.4 Unrecognized authentication type)

[truthsword]

(the timeout is because the microsoft SMTP servers are really slow to respond when you use the incorrect authentication.

Then, that maybe a Watchtower issue, as I have a notification app using the identical credentials w/o issue. I'll look for another solution. Thank you.

[nfp0]

I am also afflicted by this issue. I get the timed out error message.

Using these same credentials, for example for Nextcloud notifications, works without issue.

[jhmc93]

having the same issue can someone help with this?