Redmine

We have recently upgraded to office365 for our email platform and hadn't realised that our version of Redmine didn't support tls. I've gone through the process of setting up a new version of redmine on a new server and I'm in the process of testing before switching over. I've configured the email settings in configuration.yml as per the gmail tls example but with the relevant office365 settings. However email is still not sending.

I went through various email settings and even setup a very basic local smtp server but even this didn't work.

I've turned on logging for emails using the settings in production.rb

#config.action_mailer.logger = nil
config.log_level = :debug
config.action_mailer.perform_deliveries = false

but this didn't produce any logs

I then installed tshark on the Redmine server and tried sending a test email, the server didn't even try to send an email there was no traffic generated and sent to the email server. So it appears Redmine isn't even attempting to send an email.

I'm not sure where else to go from here, I've got full access to the server so if any more information is needed please just let me know

Environment:
  Redmine version                3.2.0.stable.15072
  Ruby version                   2.1.5-p273 (2014-11-13) [x86_64-linux-gnu]
  Rails version                  4.2.5
  Environment                    production
  Database adapter               Mysql2
SCM:
  Subversion                     1.8.10
  Filesystem
Redmine plugins:
  no plugin installed