Hello ntozierThanks for the direction. I will repost below with more info:osTicket Versionv1.10.1 (9ae093d) Web Server SoftwareMicrosoft-IIS/8.5MySQL Version5.6.36PHP Version5.6.35I've been able to setup osTickets on our server( OS Windows 2012 R2). But when trying to configure the osticket email SMTP settings (for use with gmail), I keep getting this error below:Failed to connect to smtp.gmail.com I am at a loss as to what else to do.Please help me find a solution.RegardsTesmond