Email - could not initialize transporter

Operating system

Linux

Joplin version

3.3.3

What issue do you have?

I am running Joplin Server on a Synology NAS in a Docker container. I have configured the Mailer as follows:

 MAILER_ENABLED: true
 MAILER_HOST: mail.temp.com
 MAILER_PORT: 465
 MAILER_SECURITY: starttls
 MAILER_AUTH_USER: fred@temp.com
 MAILER_AUTH_PASSWORD: *********
 MAILER_NOREPLY_NAME: fred@temp.com
 MAILER_NOREPLY_EMAIL: fred@temp.com

When I start the container, I can not send emails. I have looked in the log file and can see these error messages.

11:27:03 0|app | 2025-05-28 11:27:03: TaskService: Running #12 (Process emails) (scheduled)...
11:27:03 0|app | 2025-05-28 11:27:03: EmailService: Starting maintenance...
11:27:33 0|app | 2025-05-28 11:27:33: [error] EmailService: Could not run maintenance: Error: Could not initialize transporter. Service will be disabled: Greeting never received
11:27:33 0|app | at SMTPConnection._formatError (/home/joplin/packages/server/node_modules/nodemailer/lib/smtp-connection/index.js:798:19)
11:27:33 0|app | at SMTPConnection._onError (/home/joplin/packages/server/node_modules/nodemailer/lib/smtp-connection/index.js:784:20)
11:27:33 0|app | at Timeout. (/home/joplin/packages/server/node_modules/nodemailer/lib/smtp-connection/index.js:718:22)
11:27:33 0|app | at listOnTimeout (node:internal/timers:569:17)
11:27:33 0|app | at processTimers (node:internal/timers:512:7) {
11:27:33 0|app | code: 'ETIMEDOUT',
11:27:33 0|app | command: 'CONN'
11:27:33 0|app | }
11:27:33 0|app | 2025-05-28 11:27:33: EmailService: Maintenance completed in 30123ms
11:27:34 0|app | 2025-05-28 11:27:34: TaskService: Completed #12 (Process emails) in 32299ms

I would appreciate it if someone can help me decode and resolve this error message.

Thanks in advance.

@jmapoz welcome to the forum.

MAILER_ENABLED is marked as true, is this correct?

In my .env file it is MAILER_ENABLED=1

Does MAILER_ENABLED: 1 make any difference?

Hi @dpoulton, thanks for your welcome and suggestion. I have tried that but it has the same error message which I'll reproduce here.

13:44:40 0|app | 2025-05-28 13:44:40: [error] EmailService: Could not run maintenance: Error: Could not initialize transporter. Service will be disabled: Greeting never received
13:44:40 0|app | at SMTPConnection._formatError (/home/joplin/packages/server/node_modules/nodemailer/lib/smtp-connection/index.js:798:19)
13:44:40 0|app | at SMTPConnection._onError (/home/joplin/packages/server/node_modules/nodemailer/lib/smtp-connection/index.js:784:20)
13:44:40 0|app | at Timeout. (/home/joplin/packages/server/node_modules/nodemailer/lib/smtp-connection/index.js:718:22)
13:44:40 0|app | at listOnTimeout (node:internal/timers:569:17)
13:44:40 0|app | at processTimers (node:internal/timers:512:7) {
13:44:40 0|app | code: 'ETIMEDOUT',
13:44:40 0|app | command: 'CONN'
13:44:40 0|app | }
13:44:40 0|app | 2025-05-28 13:44:40: EmailService: Maintenance completed in 30797ms
13:44:41 0|app | 2025-05-28 13:44:41: TaskService: Completed #12 (Process emails) in 39383ms