I installed the Turnkey Redmine Streamable VMDK image with OVF, to my ESXi host, updated it and everything works just as i expected, however i would like to use this post to ask for support in changing: Postfix MTA (bound to localhost) to allow sending of email (e.g., password recovery) to using SMTP with a Google business email account i have so that mails send by this machine don't end up in the SPAM folder.

In this section i show what i did so far:

1. made a backup of file /var/www/redmine/config/configuration.yml that has following contents:

production:
  email_delivery:
    delivery_method: :sendmail
    smtp_settings:
      address: 127.0.0.1
      port: 25

and with this configuration emails are send OK but end up as spam on google

2. i then read up on and chose to use this piece of code:

# ==== SMTP server at using TLS (GMail)
#
# This might require some additional configuration. See the guides at:
# http://www.redmine.org/projects/redmine/wiki/EmailConfiguration
#
# production:
#   email_delivery:
#     delivery_method: :smtp
#     smtp_settings:
#       enable_starttls_auto: true
#       address: "smtp.gmail.com"
#       port: 587
#       domain: "smtp.gmail.com" # 'your.domain.com' for GoogleApps
#       authentication: :plain
#       user_name: "your_email@gmail.com"
#       password: "your_password"

from the configuration.yml.example

3 that i edited in to the configuration.yml as:

production:
email_delivery:
delivery_method: :smtp
smtp_settings:
enable_starttls_auto: true
address: "smtp.googlemail.com"
port: 465
domain: "********.com"
authentication: :plain
user_name: "********@********.com"
password: "********"

where ******** is personal information, and all configuration options mirror my Thunderbird configuration that works.

However this configuration doesn't do any email sending on  Turnkey Redmine Streamable VMDK image with OVF that i have and i don't know what to do next. Here is where i need your help if possible. Thanks

PS: what i think i need to do is install a SMTP client, but not sure how and if it's compatible with what i have so far.