Error Message: Could not connect to smtp host ‘ssl://smtp.office365.com’

See: https://locklizardkb.com/knowledge-base/error-message-could-not-connect-to-smtp-host-connection-timed-out-or-no-route-to-host/

If those suggestions don’t help then see http://stackoverflow.com/questions/24947434/setting-up-phpmailer-with-office365-smtp

You MUST set up a connector first (either an open SMTP relay or Client Send). Read this and it will tell you everything you need to know about allowing Office365 to send email: https://technet.microsoft.com/en-us/library/dn554323.aspx