SMTP stopped working after Docker tag 2020626 #2907

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MrUnknownDE · 2026-04-06T04:17:21+02:00

MrUnknownDE commented

2026-04-06 04:17:21 +02:00

Originally created by @RainmakerRaw on 6/26/2020

Subject of the issue

I run Synology Docker with bitwardenrs. My SMTP provider is iCloud, and the settings work fine (emails are successfully delivered, testing in the Admin page works). As soon as I upgrade the container from 2020626 to latest, emails no longer deliver. There are 'smtp error', 400 errors, and complaints about a self-signed certificate in the chain. If I revert back to 2020626 (same Docker config file, same settings, same data dir etc) things work fine again and I can send mail perfectly.

Your environment

Bitwarden_rs version: 1.15.1-b34d5482

Install method: Synology Docker using bitwardenrs/server:latest
Clients used:
Reverse proxy and version:
Version of mysql/postgresql:
Other relevant information:

Steps to reproduce

The container is launched with the following SMTP settings for iCloud (which work in 2020626):

Host: smtp.mail.me.com
Enable SSL: true
Explicit TLS: false
Port: 587
From address: My iCloud email address
From name: Bitwarden_RS
Username: My iCloud email address
Password: My secret password
Json form auth mechanism: (blank)
SMTP connection timeout: 15

Expected behaviour

A test email delivered to my own address should be sent and deliver successfully.

Actual behaviour

SMTP error.

The logs include 400 errors, and a complaint that there's a self-signed cert in the chain (this is Apple, and it doesn't complain on the older version. Other apps send mail just fine also).

As I said above, moving back to 2020626 resolves the issue immediately.

Relevant logs

Log file attached (HTML saved as PDF).
bitwardenrs-latest-log.pdf

*Originally created by @RainmakerRaw on 6/26/2020*  ### Subject of the issue I run Synology Docker with bitwardenrs. My SMTP provider is iCloud, and the settings work fine (emails are successfully delivered, testing in the Admin page works). As soon as I upgrade the container from 2020626 to latest, emails no longer deliver. There are 'smtp error', 400 errors, and complaints about a self-signed certificate in the chain. If I revert back to 2020626 (same Docker config file, same settings, same data dir etc) things work fine again and I can send mail perfectly. ### Your environment  * Bitwarden_rs version: 1.15.1-b34d5482  * Install method: Synology Docker using bitwardenrs/server:latest * Clients used:  * Reverse proxy and version:  * Version of mysql/postgresql:  * Other relevant information: ### Steps to reproduce  The container is launched with the following SMTP settings for iCloud (which work in 2020626): **Host**: smtp.mail.me.com **Enable SSL**: true **Explicit TLS**: false **Port**: 587 **From address**: My iCloud email address **From name**: Bitwarden_RS **Username**: My iCloud email address **Password**: My secret password **Json form auth mechanism**: (blank) **SMTP connection timeout**: 15 ### Expected behaviour  A test email delivered to my own address should be sent and deliver successfully. ### Actual behaviour  SMTP error. The logs include 400 errors, and a complaint that there's a self-signed cert in the chain (this is Apple, and it doesn't complain on the older version. Other apps send mail just fine also). As I said above, moving back to 2020626 resolves the issue immediately. ### Relevant logs  Log file attached (HTML saved as PDF). [bitwardenrs-latest-log.pdf](https://github.com/dani-garcia/bitwarden_rs/files/4834868/bitwardenrs-latest-log.pdf)

MrUnknownDE closed this issue

2026-04-06 04:17:21 +02:00

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Reference: github/vaultwarden#2907