Looks like a simple auth & security layer issue. Start by checking if you have sasl abstraction library and modules installed:
dpkg -l | grep sasl
Use this checklist to see if your postfix is setup correctly:
$ nano /etc/postfix/master.cf
Look up at the beginning if you have these directives:
#
# Postfix master process configuration file. For details on the format
# of the file, see the master(5) manual page (command: "man 5 master").
#
# Do not forget to execute "postfix reload" after editing this file.
#
# ==========================================================================
# service type private unpriv chroot wakeup maxproc command + args
# (yes) (yes) (yes) (never) (100)
# ==========================================================================
smtp inet n - n - - smtpd
# @josephgodwinke says: if you are using spamassissin this directive will be set automatically. If you do not have it ignore this part
# smtp inet n - n - - smtpd -o content_filter=spamassassin
#smtp inet n - n - 1 postscreen
#smtpd pass - - n - - smtpd
#dnsblog unix - - n - 0 dnsblog
#tlsproxy unix - - n - 0 tlsproxy
submission inet n - n - - smtpd
-o syslog_name=postfix/submission
-o smtpd_tls_security_level=encrypt
-o smtpd_sasl_auth_enable=yes
-o smtpd_reject_unlisted_recipient=no
-o smtpd_client_restrictions=$mua_client_restrictions
-o smtpd_helo_restrictions=$mua_helo_restrictions
-o smtpd_sender_restrictions=$mua_sender_restrictions
-o smtpd_recipient_restrictions=permit_sasl_authenticated,reject
-o milter_macro_daemon_name=ORIGINATING
smtps inet n - n - - smtpd
-o syslog_name=postfix/smtps
-o smtpd_tls_wrappermode=yes
-o smtpd_sasl_auth_enable=yes
-o smtpd_reject_unlisted_recipient=no
-o smtpd_client_restrictions=$mua_client_restrictions
Now check $ nano /etc/postfix/main.cf || vi /etc/postfix/main.cf
smtpd_sasl_type = dovecot
smtpd_sasl_path = private/auth
smtpd_sasl_auth_enable = yes
broken_sasl_auth_clients = yes
smtpd_sasl_authenticated_header = yes
smtpd_recipient_restrictions = permit_mynetworks, permit_sasl_authenticated, reject_unauth_destinat>
smtpd_use_tls = yes
smtpd_tls_cert_file = /etc/pki/dovecot/certs/dovecot.pem
smtpd_tls_key_file = /etc/pki/dovecot/private/dovecot.pem
If you just added either of these you will need to restart postfix sudo service postfix restart || sudo systemctl restart postfix
If you dont mind post your mailserver domain we see if there is an issue with ssl certificate validity