Vaultwarden Office365 SMTP Relay Configuration

Help
1

I am facing issues when attempting to utilise Office365’s SMTP relay with Vaultwarden.

My configuration is as below:

{
  "_enable_smtp": true,
  "use_sendmail": false,
  "smtp_host": "smtp.office365.com",
  "smtp_security": "force_tls",
  "smtp_port": 587,
  "smtp_from": "***@***.com",
  "smtp_from_name": "Vaultwarden",
  "smtp_username": "***@***.com",
  "smtp_password": "*******",
  "smtp_auth_mechanism": "Login",
  "smtp_timeout": 15,
  "smtp_embed_images": true,
  "smtp_accept_invalid_certs": true,
  "smtp_accept_invalid_hostnames": true,
  "_enable_email_2fa": false,
  "email_token_size": 6,
  "email_expiration_time": 600,
  "email_attempts_limit": 3
}

When attempting to send a test mail, I get the following error message:

Error sending SMTP test email
SMTP error: Connection error: Connection error: error:0A00010B:SSL routines:ssl3_get_record:wrong version number: …/ssl/record/ssl3_record.c:354:

Any support in resolving this to get mail sending successfully would be greatly appreciated.

Many thanks.

2

You need to use starttls instead of force_tls

3

Thanks for the feedback. However, using starttls as opposed to force_tls results in the error message:

Error sending SMTP test email
Undefined

This results in the email not even being attempted to be sent at all, so it is not the solution.

Any further advice?

4

Check the logs.
Also see

5

Enabling debugging was very helpful, thank you.

It was 2FA being dumb after changing to starttls

Thanks for your help.