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I feel like I get thrown around when I ask questions on these sites (superuser/stackoverflow/serverfault) so please excuse me if my question is in the wrong place and point it out to me and I'll be glad to move it else where.

I can't for the life of me receive any emails I send from my gmail account to my ubuntu server. I'm using postfix as my MTA and at first I precisely followed these instructions because they seemed to be the most straight forward and general approach, but I could never seem to even send email to my gmail account with these instructions(failed): https://help.ubuntu.com/lts/serverguide/postfix.html

After many, many hours of searching and retrying I randomly happened to come across this question, and many people in the comments to the answer claimed it really helped them so I thought I would give it a shot. When his instructions didn't work, I received similar error messages to his and eventually, I got these instructions to work (somewhat): https://serverfault.com/questions/119278/configure-postfix-to-send-relay-emails-gmail-smtp-gmail-com-via-port-587

Unfortunately - the above instructions only send email (from my linux/ubuntu) to my gmail. My biggest desire is to receive emails sent from my gmail to my linux/ubuntu. It might be helpful to note that my Ubuntu is a local web server being run off my macintosh laptop.

EDIT: I think it's important to state that I'm using ubuntu on a VM that is pointed to by a dynamic dns (freedns.afraid.org) service because I don't have a static ip given that this is a dev setup.

Here are my main.cf and master.cf files for you to pick at, any help you would like to offer me would be greatly appreciated.

main.cf :

NOTE: you will notice my #smtpd_tls_key_file and #smtpd_tls_cert_file lines are commented out. I was weary of this at first but the answer-er in the instructions that I followed explains why they can be left out for simplicity.

His explanation is the following:

Now having shown my 13 years as a systems administrator are not wasted I have email sending from my laptop through Gmail without having any need to generate a self-signed x.509 certificate as others would tell you. The key addition to the /etc/postfix/main.cf is the smtp_tls_security_level setting to may to tell Postfix that it is okay to issue the STARTTLS command when connecting to another MTA if it supports TLS.

I'm not attached to having those commented out and I'm willing to use keys and certs but it works without them for the time being and it keeps things simple. I was just going with what worked.

# 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/ssl/certs/ssl-cert-snakeoil.pem
#smtpd_tls_key_file=/etc/ssl/private/ssl-cert-snakeoil.key
#smtpd_use_tls=yes
#smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache
smtp_tls_security_level = may

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

myhostname = < my FQDN >
alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
mydestination = < my FQDN >
relayhost = smtp.gmail.com:587
mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128
mailbox_size_limit = 0
recipient_delimiter = +
inet_interfaces = all
smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
smtp_sasl_security_options =

Here is my master.cf file, the only change I made in this file is

smtp      inet  n       -       n       -       -       smtpd

that line ^ was originally this

smtp      inet  n       -       -       -       -       smtpd

to be completely honest, I don't know too much about what that small difference makes but it was recommended in many of the instructions I looked at and made no difference yet in the combination of sending/receiving mail.

so as promised, my master.cf file:

#
# 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)   (yes)   (never) (100)
# ==========================================================================
smtp      inet  n       -       n       -       -       smtpd
#smtp      inet  n       -       -       -       1       postscreen
#smtpd     pass  -       -       -       -       -       smtpd
#dnsblog   unix  -       -       -       -       0       dnsblog
#tlsproxy  unix  -       -       -       -       0       tlsproxy
#submission inet 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=$mua_sender_restrictions
#  -o smtpd_recipient_restrictions=
#  -o smtpd_relay_restrictions=permit_sasl_authenticated,reject
#  -o milter_macro_daemon_name=ORIGINATING
#smtps     inet  n       -       -       -       -       smtpd
#  -o syslog_name=postfix/smtps
#  -o smtpd_tls_wrappermode=yes
#  -o smtpd_sasl_auth_enable=yes
#  -o smtpd_reject_unlisted_recipient=no
#  -o smtpd_client_restrictions=$mua_client_restrictions
#  -o smtpd_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       -       -       -       -       qmqpd
pickup    unix  n       -       -       60      1       pickup
cleanup   unix  n       -       -       -       0       cleanup
qmgr      unix  n       -       n       300     1       qmgr
#qmgr     unix  n       -       n       300     1       oqmgr
tlsmgr    unix  -       -       -       1000?   1       tlsmgr
rewrite   unix  -       -       -       -       -       trivial-rewrite
bounce    unix  -       -       -       -       0       bounce
defer     unix  -       -       -       -       0       bounce
trace     unix  -       -       -       -       0       bounce
verify    unix  -       -       -       -       1       verify
flush     unix  n       -       -       1000?   0       flush
proxymap  unix  -       -       n       -       -       proxymap
proxywrite unix -       -       n       -       1       proxymap
smtp      unix  -       -       -       -       -       smtp
relay     unix  -       -       -       -       -       smtp
#       -o smtp_helo_timeout=5 -o smtp_connect_timeout=5
showq     unix  n       -       -       -       -       showq
error     unix  -       -       -       -       -       error
retry     unix  -       -       -       -       -       error
discard   unix  -       -       -       -       -       discard
local     unix  -       n       n       -       -       local
virtual   unix  -       n       n       -       -       virtual
lmtp      unix  -       -       -       -       -       lmtp
anvil     unix  -       -       -       -       1       anvil
scache    unix  -       -       -       -       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}

Any help or enlightenment on what may have worked for you would be great, thanks!

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