Let's say you use a Bitnami Redmine

Let’s say you use a Bitnami Redmine (version 3.3.3) image hosted by AWS:

Environment:
  Redmine version                3.3.3.stable
  Ruby version                   2.3.4-p301 (2017-03-30) [x86_64-linux]
  Rails version                  4.2.7.1
  Environment                    production
  Database adapter               Mysql2                   
Redmine plugins:
  no plugin installed

Edit configureation.yml by adding the following config block:

bitnami@ip-172-31-21-183:~/apps/redmine/htdocs/config$ sudo vi configuration.yml

default:
  email_delivery:
    delivery_method: :smtp
    smtp_settings:
      enable_starttls_auto: true
      address: smtp.gmail.com
      port: 587
      domain: example.net
      authentication: :login
      user_name: "yourusername@gmail.com"
      password: "yourpassword"

If you want to use GMail/Google Apps and other TLS-requiring SMTP servers, you’ll have to add some TLS-related settings:

production:
  email_delivery:
    delivery_method: :smtp
    smtp_settings:
      enable_starttls_auto: true
      address: "smtp.gmail.com" 
      port: 587
      domain: "smtp.gmail.com" 
      authentication: :plain
      user_name: "your_email@gmail.com" 
      password: "your_password"

Restart Redmine by the following command:

bitnami@ip-172-31-21-183:~$ sudo /opt/bitnami/ctlscript.sh restart

A little bit weird though, the Google account needs some tuning otherwise error occurs:
https://support.google.com/mail/answer/14257

You have to:
Login to your gmail account.
[1]Go to https://www.google.com/settings/security/lesssecureappsand Turn On this feature
[2]Go to https://accounts.google.com/DisplayUnlockCaptcha and click Continue

Then you can authenticate your Additional Email Address from your Gmail Account.

Useful link:
[1]http://www.redmine.org/boards/1/topics/37402
[2]https://community.bitnami.com/t/test-notification-mail-send-results-in-broken-error-message-error-sending-534-5-7-14/20719/6
[3]http://www.redmine.org/projects/redmine/wiki/EmailConfiguration