[server] SMTP connection with STARTTLS does not work

[kc9jud]

Environment

Joplin version: Joplin Server v2.2.7-beta
Platform: Linux amd64
OS specifics: Ubuntu 18.04 + Docker

Steps to reproduce

1. Set MAILER_SECURE=0 in environment configuration.
2. Restart Docker container.
3. EmailService maintenance fails.

Describe what you expected to happen

Setting secure=false for nodemailer should cause it to use STARTTLS rather than an SSL socket. However, setting MAILER_SECURE=0 does not seem to be respected:

joplin/packages/server/src/config.ts

Line 93 in f611d77

secure: !!Number(env.MAILER_SECURE) || true,

In addition, the default value of true on that line is inconsistent with the default port on the line above:

joplin/packages/server/src/config.ts

Line 92 in f611d77

port: Number(env.MAILER_PORT || 587),

(The submission port 587 normally uses STARTTLS, where as port 465 is standard for SMTPS a.k.a SMTP over SSL.)

Logfile

2021-07-21 20:01:49: [error] EmailService: Could not run maintenance: [Error: Could not initialize transporter. Service will be disabled: 140262647203648:error:1408F10B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:332:
] {
  library: 'SSL routines',
  function: 'ssl3_get_record',
  reason: 'wrong version number',
  code: 'ESOCKET',
  command: 'CONN'
}
2021-07-21 20:01:49: EmailService: Maintenance completed in 130ms

[stale]

Hey there, it looks like there has been no activity on this issue recently. Has the issue been fixed, or does it still require the community's attention? This issue may be closed if no further activity occurs. You may comment on the issue and I will leave it open. Thank you for your contributions.

[kc9jud]

Yes, this is still an issue with 2.3.7-beta:

2021-08-22 18:25:26: [error] EmailService: Could not run maintenance: [Error: 139770672543680:error:1408F10B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:332:
] {
  library: 'SSL routines',
  function: 'ssl3_get_record',
  reason: 'wrong version number',
  code: 'ESOCKET',
  command: 'CONN'
}

[stale]

Hey there, it looks like there has been no activity on this issue recently. Has the issue been fixed, or does it still require the community's attention? This issue may be closed if no further activity occurs. You may comment on the issue and I will leave it open. Thank you for your contributions.

[kc9jud]

This is still waiting on #5369.

[jinnatar]

b5d792c has solved the immediate issue of not being able to override the secure parameter. Will test if STARTSSL is feasible now.

[jinnatar]

I am unable to confirm if email sending is now functional with STARTSSL since it seems to be completely broken: #5669

[jinnatar]

I can confirm that STARTTLS is now functional when setting MAILER_SECURE=0 and per Exim4 logs it's not just an unsecured connection but encrypted as expected:

2021-11-03 14:21:33 1miH8v-0002cX-Jl <= joplinadmin+noreply@example.com H=docker1.example.com ([127.0.0.1]) [10.0.10.3] P=esmtps X=TLS1.3:ECDHE_X25519__RSA_PSS_RSAE_SHA256__AES_256_GCM:256 CV=no S=1370 id=0ed2de42-308d-3341-05ce-a1f2f9e0d5a9@example.com