Defect #37158: SMTP authentication failed - Redmine

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Defect #37158

closed

SMTP authentication failed

Added by Thijs Thiessens over 2 years ago. Updated over 2 years ago.

Status:

Closed

Priority:

Normal

Assignee:

Category:

Email notifications

Target version:

Start date:

Due date:

% Done:

Estimated time:

Resolution:

Invalid

Affected version:

4.2.5

Description

Hello all,

Sending notification has always worked for us but suddenly stopped working. The only thing that has changed is that our ISP stopped service TLS < 1.2 with smtp SSL

n-redmine | I, [2022-05-25T17:15:06.158707 #1] INFO -- : Completed 200 OK in 1455ms (Views: 444.9ms | ActiveRecord: 928.2ms)
redmine | E, [2022-05-25T17:15:07.195104 #1] ERROR -- : Email delivery error: 535 5.7.8 Error: authentication failed:
redmine |
redmine | I, [2022-05-25T17:15:07.195536 #1] INFO -- : Performed ActionMailer::DeliveryJob (Job ID: 7f01d079-8b20-4f4f-aef8-b034b54855f4) from Async(mailers) in 2505.75ms

Using openssl s_client -connect on the same host and same credentials:

220 submission10.mail.****.nl ESMTP
EHLO *
250-submission10.mail.**
250-PIPELINING
250-SIZE 37033449
250-AUTH PLAIN LOGIN
250-AUTH=PLAIN LOGIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN
AUTH LOGIN
334 VXNlcm5hbWU6
a2FudG9vckBmaWpudGh1aXN6b3JnLm5s
334 UGFzc3dvcmQ6
V2FzdDN3cnllcmMu
235 2.7.0 Authentication successful

How can I debug or progress this issue further?

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Updated by Thijs Thiessens over 2 years ago

We are using docker-compose with image: redmine:4.2.6

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Updated by Thijs Thiessens over 2 years ago

And this is a snippet from our docker-compose:

- SMTP_ENABLED=true
    - SMTP_METHOD=:smtp
    #-SMTP_DOMAIN=**
    - SMTP_HOST=smtp.**.email
    - SMTP_PORT=465
    - SMTP_USER=**
    - SMTP_PASS=**
    - SMTP_SSL=true
    - SMTP_AUTHENTICATION=:login

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Updated by Holger Just over 2 years ago

Status changed from New to Needs feedback

The authentication error you are observing there is likely unrelated to the change in TLS versions. If the TLS change would be the cause, you would get a transport-level exception, rather than an SMTP error code.

As such, it's more likely that you are using a wrong username or password in your Redmine configuration. You may verify this by checking the generated configuration.yml file within your running docker instance.

Please note that the Redmine docker image at https://hub.docker.com/_/redmine is not maintained by the Redmine project but the docker community. As such, configuration issues with this docker image can likely not be addressed by the Redmine project but must be handled by the (external) team maintaining the Redmine image at docker, e.g. at https://github.com/docker-library/redmine/issues.

(With that being said: in the openssl s_client session you have posted in your issue description, you have apparently posted your actual base64 encoded password. As this password is now publicly visible, you should consider it leaked and I strongly encourage you to change it as soon as possible.)

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