Squirrelmail Server replied: 530 5.7.0 Must issue a STARTTLS command first

Question

I am setting up squirrelmail to access it from anywhere from internet. I have installe postfix and dovecot on ubuntu 16.04. I am able to send mail to [email protected] from [email protected] with ms-outlook on my desktop. but when I try it from https://squirrelmail.mydomain.com I get

ERROR
Message not sent.
Authentication required
Server replied: 530 5.7.0 Must issue a STARTTLS command first

When I try if from https://roundcube.mydomain.com I get

SMTP Error (220): Authentication failed.

/etc/postfix/master.cf:

#
# Postfix master process configuration file.  For details on the format
# of the file, see the master(5) manual page (command: "man 5 master" or
# on-line: http://www.postfix.org/master.5.html).
#
# Do not forget to execute "postfix reload" after editing this file.
#
# ==========================================================================
# service type  private unpriv  chroot  wakeup  maxproc command + args
#               (yes)   (yes)   (no)    (never) (100)
# ==========================================================================
smtp      inet  n       -       n       -       -       smtpd
#smtp      inet  n       -       y       -       1       postscreen
#smtpd     pass  -       -       y       -       -       smtpd
#dnsblog   unix  -       -       y       -       0       dnsblog
#tlsproxy  unix  -       -       y       -       0       tlsproxy
submission inet n       -       n       -       -       smtpd
  -o smtpd_enforce_tls=yes
  -o smtpd_sasl_auth_enable=yes
  -o smtpd_client_restrictions=permit_mynetworks,permit_sasl_authenticated,reject
#  -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=$mua_sender_restrictions
#  -o smtpd_recipient_restrictions=
#  -o smtpd_relay_restrictions=permit_sasl_authenticated,reject
#  -o milter_macro_daemon_name=ORIGINATING
smtps     inet  n       -       n       -       -       smtpd
  -o syslog_name=postfix/smtps
  -o smtpd_tls_wrappermode=yes
  -o smtpd_sasl_auth_enable=yes
  -o smtpd_reject_unlisted_recipient=no
#  -o smtpd_client_restrictions=$mua_client_restrictions
  -o smtpd_client_restrictions=permit_mynetworks,permit_sasl_authenticated,reject
#  -o smtpd_helo_restrictions=$mua_helo_restrictions
#  -o smtpd_sender_restrictions=$mua_sender_restrictions
#  -o smtpd_recipient_restrictions=
#  -o smtpd_relay_restrictions=permit_sasl_authenticated,reject
#  -o milter_macro_daemon_name=ORIGINATING
#628       inet  n       -       y       -       -       qmqpd
pickup    unix  n       -       y       60      1       pickup
cleanup   unix  n       -       y       -       0       cleanup
qmgr      unix  n       -       n       300     1       qmgr
#qmgr     unix  n       -       n       300     1       oqmgr
tlsmgr    unix  -       -       y       1000?   1       tlsmgr
rewrite   unix  -       -       y       -       -       trivial-rewrite
bounce    unix  -       -       y       -       0       bounce
defer     unix  -       -       y       -       0       bounce
trace     unix  -       -       y       -       0       bounce
verify    unix  -       -       y       -       1       verify
flush     unix  n       -       y       1000?   0       flush
proxymap  unix  -       -       n       -       -       proxymap
proxywrite unix -       -       n       -       1       proxymap
smtp      unix  -       -       y       -       -       smtp
relay     unix  -       -       y       -       -       smtp
#       -o smtp_helo_timeout=5 -o smtp_connect_timeout=5
showq     unix  n       -       y       -       -       showq
error     unix  -       -       y       -       -       error
retry     unix  -       -       y       -       -       error
discard   unix  -       -       y       -       -       discard
local     unix  -       n       n       -       -       local
virtual   unix  -       n       n       -       -       virtual
lmtp      unix  -       -       y       -       -       lmtp
anvil     unix  -       -       y       -       1       anvil
scache    unix  -       -       y       -       1       scache
#
# ====================================================================
# Interfaces to non-Postfix software. Be sure to examine the manual
# pages of the non-Postfix software to find out what options it wants.
#
# Many of the following services use the Postfix pipe(8) delivery
# agent.  See the pipe(8) man page for information about ${recipient}
# and other message envelope options.
# ====================================================================
#
# maildrop. See the Postfix MAILDROP_README file for details.
# Also specify in main.cf: maildrop_destination_recipient_limit=1
#
maildrop  unix  -       n       n       -       -       pipe
  flags=DRhu user=vmail argv=/usr/bin/maildrop -d ${recipient}
#
# ====================================================================
#
# Recent Cyrus versions can use the existing "lmtp" master.cf entry.
#
# Specify in cyrus.conf:
#   lmtp    cmd="lmtpd -a" listen="localhost:lmtp" proto=tcp4
#
# Specify in main.cf one or more of the following:
#  mailbox_transport = lmtp:inet:localhost
#  virtual_transport = lmtp:inet:localhost
#
# ====================================================================
#
# Cyrus 2.1.5 (Amos Gouaux)
# Also specify in main.cf: cyrus_destination_recipient_limit=1
#
#cyrus     unix  -       n       n       -       -       pipe
#  user=cyrus argv=/cyrus/bin/deliver -e -r ${sender} -m ${extension} ${user}
#
# ====================================================================
# Old example of delivery via Cyrus.
#
#old-cyrus unix  -       n       n       -       -       pipe
#  flags=R user=cyrus argv=/cyrus/bin/deliver -e -m ${extension} ${user}
#
# ====================================================================
#
# See the Postfix UUCP_README file for configuration details.
#
uucp      unix  -       n       n       -       -       pipe
  flags=Fqhu user=uucp argv=uux -r -n -z -a$sender - $nexthop!rmail ($recipient)
#
# Other external delivery methods.
#
ifmail    unix  -       n       n       -       -       pipe
  flags=F user=ftn argv=/usr/lib/ifmail/ifmail -r $nexthop ($recipient)
bsmtp     unix  -       n       n       -       -       pipe
  flags=Fq. user=bsmtp argv=/usr/lib/bsmtp/bsmtp -t$nexthop -f$sender $recipient
scalemail-backend unix  -   n   n   -   2   pipe
  flags=R user=scalemail argv=/usr/lib/scalemail/bin/scalemail-store ${nexthop} ${user} ${extension}
mailman   unix  -       n       n       -       -       pipe
  flags=FR user=list argv=/usr/lib/mailman/bin/postfix-to-mailman.py
  ${nexthop} ${user}

/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 (Ubuntu)
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

# TLS parameters
smtpd_tls_cert_file=/etc/letsencrypt/live/mydomain.com/cert.pem
smtpd_tls_key_file=/etc/letsencrypt/live/mydomain.com/privkey.pem
smtp_tls_CAfile=/etc/letsencrypt/live/mydomain.com/fullchain.pem
smtpd_use_tls=yes
smtpd_tls_security_level=encrypt
smtpd_tls_auth_only=yes
smtp_tls_note_starttls_offer   = yes
smtpd_tls_loglevel = 1
smtpd_tls_received_header   = yes
smtpd_tls_session_cache_timeout   = 3600s
tls_random_source =   dev:/dev/urandom
smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

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

smtpd_sasl_type = dovecot
smtpd_sasl_path = private/auth
smtpd_sasl_auth_enable = yes
smtpd_sasl_security_options = noanonymous
smtpd_relay_restrictions = permit_mynetworks permit_sasl_authenticated defer_unauth_destination
myhostname = mail.mydomain.com
alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
myorigin = /etc/mailname
mydestination = $myhostname, mydomain.com, ec2.mydomain.com, localhost.mydomain.com, localhost
relayhost = 
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

/usr/share/squirrelmail.devel/config/config.php:

<?php

/**
 * SquirrelMail Configuration File
 * Created using the configure script, conf.pl
 */

$config_version = '1.5.0';
$config_use_color = 2;

$org_name      = "SquirrelMail";
$org_logo      = SM_PATH . 'images/sm_logo.png';
$org_logo_width  = '308';
$org_logo_height = '111';
$org_title     = "SquirrelMail";
$signout_page  = '';
$frame_top     = '_top';

$provider_uri     = '';

$provider_name     = '';

$motd = "";

$squirrelmail_default_language = 'en_US';
$default_charset          = 'iso-8859-1';
$show_alternative_names   = false;
$aggressive_decoding   = false;
$lossy_encoding        = false;

$domain                 = 'ferryfair.com';
$imapServerAddress      = 'localhost';
$imapPort               = 143;
$useSendmail            = false;
$smtpServerAddress      = 'localhost';
$smtpPort               = 25;
$sendmail_path          = '/usr/sbin/sendmail';
$sendmail_args          = '-i -t';
$pop_before_smtp        = false;
$pop_before_smtp_host   = '';
$imap_server_type       = 'dovecot';
$invert_time            = false;
$optional_delimiter     = 'detect';
$encode_header_key      = '';

$default_folder_prefix          = '';
$trash_folder                   = 'INBOX.Trash';
$sent_folder                    = 'INBOX.Sent';
$draft_folder                   = 'INBOX.Drafts';
$default_move_to_trash          = true;
$default_move_to_sent           = true;
$default_save_as_draft          = true;
$show_prefix_option             = false;
$list_special_folders_first     = true;
$use_special_folder_color       = true;
$auto_expunge                   = true;
$default_sub_of_inbox           = true;
$show_contain_subfolders_option = false;
$default_unseen_notify          = 2;
$default_unseen_type            = 1;
$auto_create_special            = true;
$delete_folder                  = false;
$noselect_fix_enable            = false;

$data_dir                 = '/var/local/squirrelmail/data/';
$attachment_dir           = '/var/local/squirrelmail/attach/';
$dir_hash_level           = 0;
$default_left_size        = '150';
$force_username_lowercase = false;
$default_use_priority     = true;
$hide_sm_attributions     = false;
$default_use_mdn          = true;
$edit_identity            = true;
$edit_name                = true;
$edit_reply_to            = true;
$hide_auth_header         = false;
$disable_thread_sort      = false;
$disable_server_sort      = false;
$allow_charset_search     = true;
$allow_advanced_search    = 0;

$time_zone_type           = 0;

$config_location_base     = '';

$disable_plugins          = false;
$disable_plugins_user     = '';


$user_theme_default = 0;
$user_themes[0]['PATH'] = 'none';
$user_themes[0]['NAME'] = 'Default';
$user_themes[1]['PATH'] = SM_PATH . 'css/blue_gradient/';
$user_themes[1]['NAME'] = 'Blue Options';

$icon_theme_def = 1;
$icon_theme_fallback = 3;
$icon_themes[0]['PATH'] = 'none';
$icon_themes[0]['NAME'] = 'No Icons';
$icon_themes[1]['PATH'] = 'template';
$icon_themes[1]['NAME'] = 'Template Default Icons';
$icon_themes[2]['PATH'] = SM_PATH . 'images/themes/default/';
$icon_themes[2]['NAME'] = 'Default Icon Set';
$icon_themes[3]['PATH'] = SM_PATH . 'images/themes/xp/';
$icon_themes[3]['NAME'] = 'XP Style Icons';

$templateset_default = 'default';
$templateset_fallback = 'default';
$rpc_templateset = 'default_rpc';
$aTemplateSet[0]['ID'] = 'default';
$aTemplateSet[0]['NAME'] = 'Default';
$aTemplateSet[1]['ID'] = 'default_advanced';
$aTemplateSet[1]['NAME'] = 'Advanced';

$default_fontsize = '';
$default_fontset = '';

$fontsets = array();
$fontsets['comicsans'] = 'comic sans ms,sans-serif';
$fontsets['serif'] = 'serif';
$fontsets['verasans'] = 'bitstream vera sans,verdana,sans-serif';
$fontsets['tahoma'] = 'tahoma,sans-serif';
$fontsets['sans'] = 'helvetica,arial,sans-serif';

$default_use_javascript_addr_book = false;
$addrbook_dsn = '';
$addrbook_table = 'address';

$prefs_dsn = '';
$prefs_table = 'userprefs';
$prefs_user_field = 'user';
$prefs_user_size = 128;
$prefs_key_field = 'prefkey';
$prefs_key_size = 64;
$prefs_val_field = 'prefval';
$prefs_val_size = 65536;

$addrbook_global_dsn = '';
$addrbook_global_table = 'global_abook';
$addrbook_global_writeable = false;
$addrbook_global_listing = false;

$abook_global_file = '';
$abook_global_file_writeable = false;

$abook_global_file_listing = true;

$abook_file_line_length = 2048;

$no_list_for_subscribe = false;
$smtp_auth_mech        = 'plain';
$smtp_sitewide_user    = '';
$smtp_sitewide_pass    = '';
$imap_auth_mech        = 'login';
$use_imap_tls          = 0;
$use_smtp_tls          = 0;
$display_imap_login_error = false;
$session_name          = 'SQMSESSID';
$only_secure_cookies     = true;
$disable_security_tokens = false;
$check_referrer          = '';
$use_transparent_security_image = true;

$use_iframe = false;
$ask_user_info = true;
$use_icons = true;

$use_php_recode = false;
$use_php_iconv = false;

$buffer_output = false;

$allow_remote_configtest = true;
$secured_config = true;
$sq_https_port = 443;
$sq_ignore_http_x_forwarded_headers = true;
$sm_debug_mode = SM_DEBUG_MODE_OFF;

outlook settings:

Answer 1

There are some settings you have to make!

Please edit the roundcube file /usr/share/roundcubemail/config/defaults.inc.php and replace the line $config['smtp_conn_options'] = ''null'; with this:

$config['smtp_conn_options'] = array(
 'ssl' => array(
    'verify_peer'      => false,
    'verify_peer_name' => false,
 ),
);

Since you are using system users and not virtual users, from what I was able to see in your configuration you have to login in roundcube using username/password and not username@domain / password. So in the same above file you have to replace this:

$config['mail_domain'] = 'ferryfair.com';

with:

$config['mail_domain'] = '';

Also in /etc/postfix/main.cf replace:

smtpd_tls_security_level=encrypt

with:

smtpd_tls_security_level=may

Then issue a systemctl restart postfix