this post was submitted on 29 Nov 2025
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Joplin

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Official community of Joplin - the secure open-source note-taking app.

Capture your thoughts and securely access them from any device.

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Can't send Emails from Joplin Server (feddit.org)
submitted 2 weeks ago* (last edited 2 weeks ago) by kachelkaiser@feddit.org to c/joplinapp@sopuli.xyz
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Hi,

I set up a Joplin Server on Docker om my Synology NAS. Unfortunately I can't sent any email

Here is the mailing part of my Docker Compose

Spoiler

MAILER_ENABLED: ssl MAILER_HOST: server.provider.net MAILER_PORT: 465 MAILER_SECURITY: true MAILER_AUTH_USER: xxx@example.com MAILER_AUTH_PASSWORD: totallysecure MAILER_NOREPLY_NAME: Joplin Server MAILER_NOREPLY_EMAIL: xxx@example.com

In the logs I can find this

Spoiler

[error] EmailService: Could not run maintenance: Error: Could not initialize transporter. Service will be disabled: Greeting never received

23:39:30 1|app | at SMTPConnection._formatError (/home/joplin/packages/server/node_modules/nodemailer/lib/smtp-connection/index.js:809:19)

23:39:30 1|app | at SMTPConnection._onError (/home/joplin/packages/server/node_modules/nodemailer/lib/smtp-connection/index.js:795:20)

23:39:30 1|app | at Timeout. (/home/joplin/packages/server/node_modules/nodemailer/lib/smtp-connection/index.js:729:22)

23:39:30 1|app | at listOnTimeout (node:internal/timers:569:17)

23:39:30 1|app | at processTimers (node:internal/timers:512:7) {

23:39:30 1|app | code: 'ETIMEDOUT',

23:39:30 1|app | command: 'CONN'

23:39:30 1|app | }

Any Ideas?

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[โ€“] Deebster 3 points 2 weeks ago (1 children)

I don't know much about using the Synology, can you do the normal debugging things like docker exec -it joplincontainer sh to get a shell?

Are the security settings allowing outbound connections? Can the Joplin container resolve the DNS? I'm assuming you're using an externally provided SMTP server, or is it hosted on the NAS/on your LAN too?

And have you tried those exact connection details on a different device from your house, or ideally from the NAS (with the exec sh/bash command from earlier)?

openssl s_client -connect smtp.provider.net:465 is a handy command for testing the low level connection; you should see some SSL connection debug followed by something like 220 s1.provider.net ESMTP Postfix.

[โ€“] kachelkaiser@feddit.org 1 points 2 weeks ago* (last edited 2 weeks ago)

Thank you.

I tried these things. I can get a shell using the command you gave me.

Bute the second test withj openssl does not work within the container shell because of the missing openssl command.

But it worked directly on the NAS. i got

220 mxe83f.netcup.net ESMTP Postfix (Debian/GNU) as response from the server

[โ€“] fastfinge@rblind.com 2 points 2 weeks ago (1 children)

The connection to the SMTP server is timing out. Are you sure the port and SSL config is correct?

[โ€“] kachelkaiser@feddit.org 1 points 2 weeks ago

Yes this is correct. It works using betterbird with the same settings.