Okey i installed opensmtpd-extra and tried a cleaner smtpd.conf file: 
dpaste.com/255DGXH.txt

Same authentication failed when i try in mutt

On March 7, 2018 9:25:18 PM UTC, ed...@pettijohn-web.com wrote:
>You have to install opensmtpd-extras package to use the passwd table.
>On Mar 7, 2018 3:21 PM, flipchan <flipc...@riseup.net> wrote:
>>
>> Yeah, they are encrypted using smtpctl and the syntax with space
>doesnt work and in other ppls configurations they have passwd instead
>of file but its not supported anymore it seems like
>>
>> On March 7, 2018 3:19:18 PM UTC, trondd <tro...@kagu-tsuchi.com>
>wrote:
>> >On Wed, March 7, 2018 10:06 am, flipchan wrote:
>> >> smtpctl encrypt mypassword
>> >>
>> >> Then syntax
>> >> user:password ?
>> >>
>> >> On March 6, 2018 9:46:26 PM UTC, trondd <tro...@kagu-tsuchi.com>
>> >wrote:
>> >>>On Tue, March 6, 2018 1:48 pm, flipchan wrote:
>> >>>> Hello,
>> >>>> im trying to create a mail server and i keep getting opensmtpd
>> >>>> authentication fail
>> >>>>
>> >>>>
>> >>>> i tried using neomutt and regular mutt, but no success
>> >>>>
>> >>>>
>> >>>> tail -f /var/log/maillog
>> >>>> Mar  6 18:15:37 mail dovecot: imap-login: Login:
>> >>>user=<u...@mysite.com>,
>> >>>> method=PLAIN, rip=homeip, lip=server, mpid=54071, TLS,
>> >>>> session=<GUjwbcJm/VRe/m7Z>
>> >>>> Mar  6 18:15:48 mail dovecot: imap-login: Login:
>> >>>user=<u...@mysite.com>,
>> >>>> method=PLAIN, rip=homeip, lip=server, mpid=11081, TLS,
>> >>>> session=<LwGSbsJm7oRe/m7Z>
>> >>>> Mar  6 18:15:55 mail smtpd[77144]: 7b289a2a8f3efe40 smtp
>> >>>event=connected
>> >>>> address=homeip host=homeip
>> >>>> Mar  6 18:15:55 mail smtpd[77144]: 7b289a2a8f3efe40 smtp
>> >>>event=starttls
>> >>>> address=homeip host=homeip ciphers="version=TLSv1.2,
>> >>>> cipher=ECDHE-RSA-AES256-GCM-SHA384, bits=256"
>> >>>> Mar  6 18:15:55 mail smtpd[77144]: 7b289a2a8f3efe40 smtp
>> >>>> event=authentication user=user address=homeip host=homeip
>> >>>result=permfail
>> >>>> Mar  6 18:15:56 mail smtpd[77144]: 7b289a2a8f3efe40 smtp
>> >>>> event=failed-command address=homeip host=homeip command="AUTH
>PLAIN
>> >>>(...)"
>> >>>> result="535 Authentication failed"
>> >>>> Mar  6 18:15:57 mail smtpd[77144]: 7b289a2a8f3efe40 smtp
>> >event=closed
>> >>>> address=homeip host=homeip reason=disconnect
>> >>>>
>> >>>>
>> >>>>
>> >>>>
>> >>>>
>> >>>> dovecot works so i can get imap but opensmtpd does work
>> >>>>
>> >>>> im using openbsd6.2
>> >>>>
>> >>>>
>> >>>> # cat /etc/mail/smtpd.conf
>> >>>> pki mail.mysite.com certificate "/etc/ssl/mail.mysite.com.crt"
>> >>>> pki mail.mysite.com key "/etc/ssl/private/mail.mysite.com.key"
>> >>>>
>> >>>> # tables setup
>> >>>> table aliases file:/etc/mail/aliases
>> >>>> table domains file:/etc/mail/domains
>> >>>> table passwd file:/etc/mail/passwd
>> >>>> table virtuals file:/etc/mail/virtuals
>> >>>>
>> >>>> # listen ports setup
>> >>>> #listen on lo0
>> >>>> listen on vio0 port 25 tls-require pki mail.mysite.com
>> >>>> #listen on vio0 port 587 tls-require pki mail.mysite.com auth
>> >>><passwd>
>> >>>> listen on vio0 port 587 smtps pki mail.mysite.com auth <passwd>
>> >>>> # special case for gmail to avoid ipv6 here
>> >>>> #limit mta for domain gmail.com inet4
>> >>>>
>> >>>> # allow local messages
>> >>>> accept from local for local alias <aliases> deliver to lmtp
>> >>>> "/var/dovecot/lmtp" rcpt-to
>> >>>> # allow virtual domains
>> >>>> accept from any for domain <domains> virtual <virtuals> deliver
>to
>> >>>lmtp
>> >>>> "/var/dovecot/lmtp" rcpt-to
>> >>>> # allow outgoing mails
>> >>>> accept from local for any relay
>> >>>> #reject from ! source <other-relays> sender "@mysite.com" for
>any
>> >>>>
>> >>>>
>> >>>>
>> >>>> both dovecot and smtpd reads passwd's from /etc/mail/passwd and
>> >only
>> >>>> dovecot works, think its some kind of smtpd config that is
>wrong...
>> >>>>
>> >>>
>> >>>Is the password encrypted properly?
>> >>>
>> >>>   In a listener context, the credentials are a mapping of
>username
>> >and
>> >>>     encrypted passwords:
>> >>>
>> >>>           user1
>> >>>$2b$10$hIJ4QfMcp.90nJwKqGbKM.MybArjHOTpEtoTV.DgLYAiThuoYmTSe
>> >>>           user2
>> >>>$2b$10$bwSmUOBGcZGamIfRuXGTvuTo3VLbPG9k5yeKNMBtULBhksV5KdGsK
>> >>>
>> >>>     The passwords are to be encrypted using the smtpctl(8)
>encrypt
>> >>>     subcommand.
>> >>
>> >> --
>> >> Take Care Sincerely flipchan layerprox dev
>> >>
>> >
>> >This comes from the table(5) man page.
>> >
>> >The file will be:
>> >username encryptedpassword
>>
>> -- 
>> Take Care Sincerely flipchan layerprox dev

-- 
Take Care Sincerely flipchan layerprox dev

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