Hi,

Do you get any errors using ’doas smtpd -n’?

Can you tried to add this ‘listen’ statement in your smtpd.conf -  (This is how 
I have my setup)

listen on egress mask-src port submission tls-require pki mail.example.com auth

Another option is to try a different password.
Now, test the login credentials using the ‘openssl’ command as noted by Edgar 
in a previous email.

Converting the plain text data to a ‘base64’, I use the following command on my 
MacBook. 

echo -n u...@example.com  | base64
Base64 Output

echo -n password | base64
Base64 Output

openssl s_client -connect mail.example.com:587 -starttls smtp
…….(SSL Output)
250 HELP

Within the smtp session I enter the commands ‘ehlo’ and ‘auth login’ 
respectively;

ehlo mail.example.com
250-mail.example.com Hello mail.example.com [x.x.x.x], pleased to meet you
250-8BITMIME
250-ENHANCEDSTATUSCODES
250-SIZE 36700160
250-DSN
250-AUTH PLAIN LOGIN
250 HELP

auth login
334 VXNlcm5hbWU6
Base64 Username (As noted above from the conversion of plain text to base64)
334 UGFzc3dvcmQ6
Base64 Password (As noted above from the conversion of plain text to base64)
235 2.0.0: Authentication succeeded

Nino



> On 14 Jan 2019, at 10:47 am, Flipchan <flipc...@riseup.net> wrote:
> 
> I changed mask-src and tried some other stuff still without success when 
> using openssl ehlo test and auth login , all i get is authentication failed , 
> i have verified that the password is legit but no luck
> 
> On January 12, 2019 11:37:42 PM GMT+01:00, Carlin Bingham <c...@walcyrge.org> 
> wrote:
>> On Sat, Jan 12, 2019 at 05:36:11PM +0100, Flipchan wrote:
>>> Hey, am tryin to upgrade my opensmtpd 
>>> email server running on openbsd 6.3 towards a new one on 6.4, 
>>> i have used a simple config with the new syntax:
>>> cat /etc/mail/smtpd.conf 
>>> 
>>> table aliases file:/etc/mail/aliases 
>>> 
>>> #table other-relays file:/etc/mail/other-relays 
>>> 
>>> pki mail.example.com cert "/etc/ssl/mail.example.com.crt" 
>>> pki mail.example.com key "/etc/ssl/private/mail.example.com.key" 
>>> 
>>> listen on lo0 
>>> listen on vio0 port 587 hostname example.com tls-require pki
>> mail.example.com auth mask-source 
>> 
>> mask-source was changed to mask-src 
>> 
>> I think because mask-source is no longer a valid keyword its being
>> interpreted as a parameter to auth.
>> 
>> 
>> --
>> Carlin
> 
> -- 
> Sent from my Android device with K-9 Mail. Please excuse my brevity.

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