Hi guy, I’ve managed to get bitwarden up and running in a docker instance as per the instructions provided by bitwarden here.

Its up and available inside and outside the local network but I can’t figure out how to get it to connect to an email provider so it can send verification emails and invitations. I used my Microsoft hosted email, lets call it [email protected] (domain provided by a 3rd party).

I’ve edited the global.override.env file to suit the values given by Microsoft and opened port 587 in my router, (unclear whether they want SSL or TLS but I’ve tried both)

I’ve also tried to connect with my gmail but no luck. When I try to verify my email I just get “An unhandled server error has occurred”

Bitwarden is also accessed through bitwarden.mydomain.com.au in this example.

Can anyone point me in the right direction, or even let me know where I might find relevant logs. the stuff in the /bwdata/ folder hasn’t been very helpful.

The only thing I can think of is that when I run “docker ps” in the terminal, none of the bitwarden related containers seem to be specifically passing port 587 through, but that was never mentioned in the guide, and I don’t know which container would need it.

Thanks

EDIT: I’ve closed port 587. I also ran the recommended telnet commands to check if I could get to the STMP server and got back a response including STARTTLS so that all good

I found these log entries in the api folder.

With my Microsoft account info

2023-09-10 12:12:42.840 +00:00 [Information] Api started.
2023-09-10 12:13:36.357 +00:00 [Error] 535: 5.7.139 Authentication unsuccessful, the request did not meet the criteria to be authenticated successfully. Contact your administrator>

MailKit.Security.AuthenticationException: 535: 5.7.139 Authentication unsuccessful, the request did not meet the criteria to be authenticated successfully. Contact your administrator>

 ---> MailKit.Net.Smtp.SmtpCommandException: 5.7.139 Authentication unsuccessful, the request did not meet the criteria to be authenticated successfully. Contact your administrator>
   --- End of inner exception stack trace ---

With google info

2023-09-10 12:00:34.585 +00:00 [Error] 534: 5.7.9 Application-specific password required. Learn more at
5.7.9  https://support.google.com/mail/?p=InvalidSecondFactor i8-20020a17090a2ac800b002696aeb72e5sm6280939pjg.2 - gsmtp

MailKit.Security.AuthenticationException: 534: 5.7.9 Application-specific password required. Learn more at
5.7.9  https://support.google.com/mail/?p=InvalidSecondFactor i8-20020a17090a2ac800b002696aeb72e5sm6280939pjg.2 - gsmtp

 ---> MailKit.Net.Smtp.SmtpCommandException: 5.7.9 Application-specific password required. Learn more at
5.7.9  https://support.google.com/mail/?p=InvalidSecondFactor i8-20020a17090a2ac800b002696aeb72e5sm6280939pjg.2 - gsmtp

I then followed the link supplied by google, it leads to a page about two factor authentication and app passwords. After enabling two factor authentication, generating an app password through gmail and using that password in the global.override.env file it’s now all working.

Thanks for your help guys.

Still can’t figure out how to get an app password from Microsoft though.

  • BrickfrogEnglish
    4•1 year ago

    and opened port 587 in my router

    Agreed with the other comment, you definitely don’t need or want to do that on your end. Note that your self hosted instance is trying to establish an outgoing connection with a random port to port 587 at wherever your hosted email is e.g. yourdockeripaddress:randomport --> mydomain.com.au:587

    I don’t have Bitwarden self hosted so can’t offer much advice on a solution but…

    I’ve also tried to connect with my gmail but no luck. When I try to verify my email I just get “An unhandled server error has occurred”

    This makes me think there’s something off with your environment, or the Bitwarden instance itself. Is there a way for you to verify that you can actually use those SMTP servers outside of Bitwarden? This sounds silly but in the past I’ve done a test installation of an email client with ability to connect to 3rd party SMTP servers e.g. Thunderbird just to verify my own internet connection can actually initiate an SMTP connection to an external server. You want to at least rule out that the hosted email server isn’t blocking you and/or have some over-active firewall on your end blocking things.

    This is all in the absence of more verbose logging (not sure if Docker or Bitwarden can give you that, something worth checking).