set no bouncemail
poll outlook.office365.com with protocol imap
port 993
auth password
user user@domain.com password password
ssl
sslfingerprint "<Correct Fingerprint - not sure if I should copy this here>"
sslcertpath /Users/myuser/.certs
keep
no rewrite
mda "/usr/local/bin/procmail -f %F -d %T";

VERBOSE=yes
:0
! myusername@gmail.com

procmail: Executing "/usr/sbin/sendmail,-oi,myusername@gmail.com"

$ sudo port install ssmtp
...

root=FIXME@gmail.com
mailhub=smtp.gmail.com:587
rewriteDomain=gmail.com
hostname=localhost
UseTLS=Yes
UseSTARTTLS=Yes
AuthUser=FIXME@gmail.com
AuthPass=Hunter2
FromLineOverride=no

...
mda "/opt/local/sbin/ssmtp FIXME"

mydomain_fallback = localhost
mail_owner = _postfix
setgid_group = _postdrop
relayhost = smtp.gmail.com:587
smtp_sasl_auth_enable = yes
smtp_sasl_password_maps=hash:/etc/postfix/sasl_passwd
smtp_sasl_security_options = noanonymous
smtp_use_tls = yes
#smtp_tls_security_level = encrypt
#tls_random_source = dev:/dev/urandom
smtp_sasl_mechanism_filter = login
smtp_sasl_mechanism_filter = login

smtp.gmail.com:587 username@gmail.com:password

date | mail -s test test@testdomain.com