# echo -e "Subject:Hello World nn Testing emailn" | sendmail root
# echo "testing" | mail -s "test message" root

Dec 29 12:56:13 pve postfix/pickup[32080]: DB1E662DFA: uid=0 from=<root>
Dec 29 12:56:13 pve postfix/cleanup[32097]: DB1E662DFA: message-id=<20171229175613.DB1E662DFA@pve.home.com>
Dec 29 12:56:13 pve postfix/qmgr[32081]: DB1E662DFA: from=<root@pve.home.com>, size=390, nrcpt=1 (queue active)
Dec 29 12:56:13 pve postfix/cleanup[32097]: E13A162DF8: message-id=<20171229175613.DB1E662DFA@pve.home.com>
Dec 29 12:56:13 pve postfix/local[32099]: DB1E662DFA: to=<root@pve.home.com>, orig_to=<root>, relay=local, delay=0.04, delays=0.03/0.01/0/0, dsn=2.0.0, status=sent (forwarded as E13A162DF8)
Dec 29 12:56:13 pve postfix/qmgr[32081]: E13A162DF8: from=<root@pve.home.com>, size=515, nrcpt=1 (queue active)
Dec 29 12:56:13 pve postfix/qmgr[32081]: DB1E662DFA: removed
Dec 29 12:56:13 pve postfix/smtp[32100]: connect to smtp.gmail.com[2607:f8b0:4001:c1d::6c]:587: Network is unreachable
Dec 29 12:56:14 pve postfix/smtp[32100]: E13A162DF8: to=<someone@icloud.com>, orig_to=<root>, relay=smtp.gmail.com[74.125.126.109]:587, delay=0.85, delays=0/0.03/0.37/0.45, dsn=2.0.0, status=sent (250 2.0.0 OK 1514570174 f126sm11045770ioa.84 - gsmtp)
Dec 29 12:56:14 pve postfix/qmgr[32081]: E13A162DF8: removed

Dec 29 12:59:40 pve postfix/pickup[32080]: D6C9362DFA: uid=0 from=<root>
Dec 29 12:59:40 pve postfix/cleanup[32429]: D6C9362DFA: message-id=<20171229175940.D6C9362DFA@pve.home.com>
Dec 29 12:59:40 pve postfix/qmgr[32081]: D6C9362DFA: from=<root@pve.home.com>, size=280, nrcpt=1 (queue active)
Dec 29 12:59:40 pve postfix/cleanup[32429]: DDD4D62DF8: message-id=<20171229175940.D6C9362DFA@pve.home.com>
Dec 29 12:59:40 pve postfix/local[32431]: D6C9362DFA: to=<root@pve.home.com>, orig_to=<root>, relay=local, delay=0.05, delays=0.03/0.01/0/0.01, dsn=2.0.0, status=sent (forwarded as DDD4D62DF8)
Dec 29 12:59:40 pve postfix/qmgr[32081]: DDD4D62DF8: from=<root@pve.home.com>, size=405, nrcpt=1 (queue active)
Dec 29 12:59:40 pve postfix/qmgr[32081]: D6C9362DFA: removed
Dec 29 12:59:41 pve postfix/smtp[32432]: connect to smtp.gmail.com[2607:f8b0:4001:c1d::6c]:587: Network is unreachable
Dec 29 12:59:41 pve postfix/smtp[32432]: DDD4D62DF8: to=<someone@icloud.com>, orig_to=<root>, relay=smtp.gmail.com[74.125.126.109]:587, delay=0.93, delays=0.01/0.02/0.52/0.38, dsn=2.0.0, status=sent (250 2.0.0 OK 1514570381 a69sm13573861itc.18 - gsmtp)
Dec 29 12:59:41 pve postfix/qmgr[32081]: DDD4D62DF8: removed

root: aaron.sullivan@icloud.com

postmaster: root
nobody: root
hostmaster: root
webmaster: root
www:root

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

myhostname=pve.home.com

smtpd_banner = $myhostname ESMTP $mail_name (Debian/GNU)
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

alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
myorigin = /etc/mailname
mydestination = $myhostname, localhost.$mydomain, localhost
#relayhost =
mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128
mailbox_size_limit = 0
inet_interfaces = loopback-only
recipient_delimiter = +

# sets gmail as relay
relayhost = [smtp.gmail.com]:587

#  use tls
smtp_use_tls=yes

# use sasl when authenticating to foreign SMTP servers
smtp_sasl_auth_enable = yes

# path to password map file
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd

# list of CAs to trust when verifying server certificate
smtp_tls_CAfile = /etc/ssl/certs/Equifax_Secure_CA.pem
smtp_tls_session_cache_database = btree:/var/lib/postfix/smtp_tls_session_cache
smtp_tls_session_cache_timeout = 3600s

# eliminates default security options which are imcompatible with gmail
smtp_sasl_security_options =

127.0.0.1 localhost.localdomain localhost
127.0.1.1 pve.home.com pve pvelocalhost

# The following lines are desirable for IPv6 capable hosts

::1     ip6-localhost ip6-loopback
fe00::0 ip6-localnet
ff00::0 ip6-mcastprefix
ff02::1 ip6-allnodes
ff02::2 ip6-allrouters
ff02::3 ip6-allhosts

pve.home.com