Sending e-mails not possible (Authentication unsuccessful)

Hello,

since I switched from the official Bitwarden to Vaultwarden, my mail delivery unfortunately doesn’t work anymore. I get the following output

[2021-10-04 10:09:25.915][request][INFO] POST /admin/test/smtp/
[2021-10-04 10:09:26.024][lettre::transport::smtp::client::connection][DEBUG] << 220 mx.mydomain.de<CRLF>
[2021-10-04 10:09:26.024][lettre::transport::smtp::client::connection][DEBUG] Wrote: EHLO bitwarden-censored<CRLF>
[2021-10-04 10:09:26.025][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>
[2021-10-04 10:09:26.025][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>
[2021-10-04 10:09:26.025][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>
[2021-10-04 10:09:26.025][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>
[2021-10-04 10:09:26.026][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>
[2021-10-04 10:09:26.026][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>
[2021-10-04 10:09:26.026][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>
[2021-10-04 10:09:26.026][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>250-AUTH NTLM<CRLF>
[2021-10-04 10:09:26.027][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>250-AUTH NTLM<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>
[2021-10-04 10:09:26.027][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>250-AUTH NTLM<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>
[2021-10-04 10:09:26.027][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>250-AUTH NTLM<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>
[2021-10-04 10:09:26.027][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>250-AUTH NTLM<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>
[2021-10-04 10:09:26.028][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>250-AUTH NTLM<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>250-SMTPUTF8<CRLF>
[2021-10-04 10:09:26.028][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>250-AUTH NTLM<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>250-SMTPUTF8<CRLF>250 XRDST<CRLF>
[2021-10-04 10:09:26.028][lettre::transport::smtp::client::connection][DEBUG] server AB-S-EX.mydomain.de with {StartTls, EightBitMime, SmtpUtfEight}
[2021-10-04 10:09:26.029][lettre::transport::smtp::client::connection][DEBUG] Wrote: STARTTLS<CRLF>
[2021-10-04 10:09:26.030][lettre::transport::smtp::client::connection][DEBUG] << 220 2.0.0 SMTP server ready<CRLF>
[2021-10-04 10:09:26.054][lettre::transport::smtp::client::connection][DEBUG] connection encrypted
[2021-10-04 10:09:26.055][lettre::transport::smtp::client::connection][DEBUG] Wrote: EHLO bitwarden-6c84549946-9ztjc<CRLF>
[2021-10-04 10:09:26.056][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>
[2021-10-04 10:09:26.056][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>
[2021-10-04 10:09:26.056][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>
[2021-10-04 10:09:26.056][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>
[2021-10-04 10:09:26.056][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>
[2021-10-04 10:09:26.056][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH NTLM LOGIN<CRLF>
[2021-10-04 10:09:26.056][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH NTLM LOGIN<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>
[2021-10-04 10:09:26.056][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH NTLM LOGIN<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>
[2021-10-04 10:09:26.056][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH NTLM LOGIN<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>
[2021-10-04 10:09:26.056][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH NTLM LOGIN<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>
[2021-10-04 10:09:26.057][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH NTLM LOGIN<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>250-SMTPUTF8<CRLF>
[2021-10-04 10:09:26.057][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH NTLM LOGIN<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>250-SMTPUTF8<CRLF>250 XRDST<CRLF>
[2021-10-04 10:09:26.057][lettre::transport::smtp::client::connection][DEBUG] Wrote: AUTH LOGIN<CRLF>
[2021-10-04 10:09:26.058][lettre::transport::smtp::client::connection][DEBUG] << 334 CENSORED<CRLF>
[2021-10-04 10:09:26.058][lettre::transport::smtp::commands][DEBUG] auth encoded challenge: CENSORED
[2021-10-04 10:09:26.058][lettre::transport::smtp::commands][DEBUG] auth decoded challenge: Username:
[2021-10-04 10:09:26.058][lettre::transport::smtp::client::connection][DEBUG] Wrote: CENSORED==<CRLF>
[2021-10-04 10:09:26.059][lettre::transport::smtp::client::connection][DEBUG] << 334 CENSORED<CRLF>
[2021-10-04 10:09:26.059][lettre::transport::smtp::commands][DEBUG] auth encoded challenge: CENSORED
[2021-10-04 10:09:26.059][lettre::transport::smtp::commands][DEBUG] auth decoded challenge: Password:
[2021-10-04 10:09:26.059][lettre::transport::smtp::client::connection][DEBUG] Wrote: CENSORED<CRLF>
[2021-10-04 10:09:31.190][lettre::transport::smtp::client::connection][DEBUG] << 535 5.7.3 Authentication unsuccessful<CRLF>
[2021-10-04 10:09:31.190][lettre::transport::smtp::client::connection][DEBUG] Wrote: QUIT<CRLF>
[2021-10-04 10:09:31.191][lettre::transport::smtp::client::connection][DEBUG] << 221 2.0.0 Service closing transmission channel<CRLF>
[2021-10-04 10:09:31.191][vaultwarden::mail][ERROR] SMTP 5xx error: lettre::transport::smtp::Error { kind: Permanent(Code { severity: PermanentNegativeCompletion, category: Unspecified3, detail: Five }) }
[2021-10-04 10:09:31.237][response][INFO] POST /admin/test/smtp (test_smtp) => 400 Bad Request

It seems that the connection is being established. However, the login does not seem to work? I used the data and logged into the web portal of the email server, this worked without any problems, so the data is correct.

Does anyone have any ideas?

Greetings
Schmandre

Try to change the auth method from login to plain and see what happens.

Thank you for the fast reply. Already tried this. The result is, that I got an error with “No compatible authentication mechanism was found”

Here the “complete” log:

[2021-10-04 15:57:09.231][lettre::transport::smtp::client::connection][DEBUG] << 220 mx.mydomain.de<CRLF>
[2021-10-04 15:57:09.231][lettre::transport::smtp::client::connection][DEBUG] Wrote: EHLO bitwarden-6c84549946-9ztjc<CRLF>
[2021-10-04 15:57:09.232][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>
[2021-10-04 15:57:09.232][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>
[2021-10-04 15:57:09.232][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>
[2021-10-04 15:57:09.232][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>
[2021-10-04 15:57:09.232][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>
[2021-10-04 15:57:09.232][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>
[2021-10-04 15:57:09.232][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>
[2021-10-04 15:57:09.232][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>250-AUTH NTLM<CRLF>
[2021-10-04 15:57:09.232][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>250-AUTH NTLM<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>
[2021-10-04 15:57:09.232][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>250-AUTH NTLM<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>
[2021-10-04 15:57:09.233][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>250-AUTH NTLM<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>
[2021-10-04 15:57:09.233][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>250-AUTH NTLM<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>
[2021-10-04 15:57:09.233][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>250-AUTH NTLM<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>250-SMTPUTF8<CRLF>
[2021-10-04 15:57:09.233][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-X-ANONYMOUSTLS<CRLF>250-AUTH NTLM<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>250-SMTPUTF8<CRLF>250 XRDST<CRLF>
[2021-10-04 15:57:09.233][lettre::transport::smtp::client::connection][DEBUG] server AB-S-EX.mydomain.de with {StartTls, SmtpUtfEight, EightBitMime}
[2021-10-04 15:57:09.233][lettre::transport::smtp::client::connection][DEBUG] Wrote: STARTTLS<CRLF>
[2021-10-04 15:57:09.234][lettre::transport::smtp::client::connection][DEBUG] << 220 2.0.0 SMTP server ready<CRLF>
[2021-10-04 15:57:09.259][lettre::transport::smtp::client::connection][DEBUG] connection encrypted
[2021-10-04 15:57:09.260][lettre::transport::smtp::client::connection][DEBUG] Wrote: EHLO bitwarden-censored<CRLF>
[2021-10-04 15:57:09.261][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>
[2021-10-04 15:57:09.261][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>
[2021-10-04 15:57:09.261][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>
[2021-10-04 15:57:09.261][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>
[2021-10-04 15:57:09.261][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>
[2021-10-04 15:57:09.261][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH NTLM LOGIN<CRLF>
[2021-10-04 15:57:09.261][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH NTLM LOGIN<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>
[2021-10-04 15:57:09.261][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH NTLM LOGIN<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>
[2021-10-04 15:57:09.261][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH NTLM LOGIN<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>
[2021-10-04 15:57:09.261][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH NTLM LOGIN<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>
[2021-10-04 15:57:09.261][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH NTLM LOGIN<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>250-SMTPUTF8<CRLF>
[2021-10-04 15:57:09.261][lettre::transport::smtp::client::connection][DEBUG] << 250-AB-S-EX.mydomain.de Hello [192.168.0.120]<CRLF>250-SIZE 37748736<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH NTLM LOGIN<CRLF>250-X-EXPS GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>250-SMTPUTF8<CRLF>250 XRDST<CRLF>
[2021-10-04 15:57:09.261][vaultwarden::mail][ERROR] SMTP Client error: internal client error: No compatible authentication mechanism was found

Seems your mail server only supports login.
And looking at the previous message you got it really says a wrong user or pass.

Does your password use any special characters?
If so, look here: SMTP Configuration · dani-garcia/vaultwarden Wiki · GitHub

Thank you again for the quick feedback. The username is the email address and contains an “@” sign. The password only consists of letters and numbers. The login to the mail server itself does not cause any problems here either, so I am definitely using the correct login data.

Does the “@” character in the user name also have to be escaped?

No, the @ shouldn’t be escaped.
Though, i can’t make more out of it the the credentials are not ok.

I saw you are using the debug function already.

It also outputs the username and password it sends as a base64 string. I would suggest to extract those values use echo -n 'base64-string' | base64 -d and match what you inputted.

The result from decrypt is matching the original input. So credentials are correct :frowning:
Password is 24 characters long. Is this maybe too much?

That isn’t to much, at least not if other clients do except it. But still, the server says no.
So, both username and password are correct?

It just is strange. Do other clients you use also use login as the method or ntlm?

If you are able, you could try to lower and even increase the password length and see what happens.

Else try it manually your self, some pointers here: Sending Email with SMTP Authentication via Telnet or OpenSSL | Windows OS Hub

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Thank you very much.

After checking the whole thing via telnet, I saw that auth ntlm is offered instead of auth login. Is it possible to use this login method anyway?

Screenshot is attached.

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ntlm is not supported by the library we use.
It’s also not very wide supported.

Also, it could be that when not using starttls login auth could not be supported.

See GitHub - steveliles/manual-ntlm: node.js scripts to help with manually testing NTLM auth via telnet / openssl

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Okay. Thank you.

So correct me if Iam wrong. I have no chance to get this working using ntlm and must setup login method?

Well, using starttls the LOGIN auth is available, so that is the only way.

NTLM is not possible.

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Many thanks for your support! I was able to finally solve the problem. After I created a new receive connector on the Exchange and set the permissions accordingly, it was possible to send emails via the Admin Portal. Thank you very much for your support in finding the solution!

Problem is solved!

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A great to hear.
Glad you got it to work.