535 Authentication failed. Restarting authentication process. 535 Authentication failed...

Topic: 535 Authentication failed. Restarting authentication process.

Post 535 Authentication failed. Restarting authentication process.
by cowboy0629 on Thursday, August 31, 2017

I have been trying to solve this problem for 2 days now I can receive email from everywhere internal and external.... I can send email to my internal network I just can't send email to external networks such as Joe@somecompany.com

My Server is Linux based using Debian (stretch) on raspberry pi using the Postfix & Dovecot

my isp blocks port 25 incoming and outgoing so I am using

store/forward (working great)


Outbound SMTP Relay (SEEMS TO BE THE PROBLEM)

/var/log/mail.cf
(SASL authentication failed; server relay.dynu.com[199.233.237.19] said: 535 Authentication failed. Restarting authentication process.)


/etc/postfix/main.cf

# See /usr/share/postfix/main.cf.dist for a commented, more complete version


# Debian specific: Specifying a file name will cause the first
# line of that file to be used as the name. The Debian default
# is /etc/mailname.
#myorigin = /etc/mailname

smtpd_banner = $myhostname ESMTP $mail_name (Raspbian)
biff = no

# appending .domain is the MUA's job.
append_dot_mydomain = no

# Uncomment the next line to generate "delayed mail" warnings
#delay_warning_time = 4h

readme_directory = no

# See http://www.postfix.org/COMPATIBILITY_README.html -- default to 2 on
# fresh installs.
compatibility_level = 2

# TLS parameters
#smtpd_tls_cert_file=/etc/ssl/certs/ssl-cert-snakeoil.pem
#smtpd_tls_key_file=/etc/ssl/private/ssl-cert-snakeoil.key
smtpd_tls_cert_file=/etc/letsencrypt/live/mail.mydomain.com/fullchain.pem
smtpd_tls_key_file=/etc/letsencrypt/live/mail.mydomain.com/privkey.pem
smtpd_use_tls=yes
smtpd_use_auth_only = yes
smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

smtpd_sasl_type = dovecot
smtpd_sasl_path = private/auth
smtpd_sasl_auth_enable = yes


smtpd_recipient_restrictions =
permit_sasl_authenticated,
permit_mynetworks,
reject_unauth_destination

## DYNU

smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
smtp_sasl_security_options =

# See /usr/share/doc/postfix/TLS_README.gz in the postfix-doc package for
# information on enabling SSL in the smtp client.

smtpd_relay_restrictions = permit_mynetworks permit_sasl_authenticated defer_unauth_destination
#myhostname = tilleys.mydomain.com
myhostname = mail.mydomain.com
alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
myorigin = /etc/mailname
mydestination = $myhostname, localhost.localdomain, localhost, mail.mydomain.com
#mydestination = localhost
relayhost = [relay.dynu.com]:26
smtp_generic_maps = hash:/etc/postfix/generic
mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128
mailbox_size_limit = 0
recipient_delimiter = +
inet_interfaces = all
inet_protocols = all


#Handing off local delivery to Dovecot's LMTP, and telling it where to store mail
virtual_transport = lmtp:unix:private/dovecot-lmtp

#Virtual domains, users, and aliases
virtual_mailbox_domains = mysql:/etc/postfix/mysql-virtual-mailbox-domains.cf
virtual_mailbox_maps = mysql:/etc/postfix/mysql-virtual-mailbox-maps.cf
virtual_alias_maps = mysql:/etc/postfix/mysql-virtual-alias-maps.cf


/etc/postfix/sasl_passwd
relay.dynu.com          relay@relay.mydomain.com:Password


/etc/postfix/generic (not sure if I actually need this or not??


miked@mydomain miked@mydomain.com
miked@mydomain.com miked@mydomain.com

root@mydomain miked@mydomain.com
root@mydomain.com miked@mydomain.com



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Post Re: 535 Authentication failed. Restarting authentication process.
by vesey on Thursday, August 31, 2017

Looks like an authentication issue on outbound relay service. Did you try resetting the password?

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Monday, December 18, 2017 3:23 PM