Well, I got my firs Mac ever for Christmas, ironically I have been an adamant PC fanatic since the dawn of the 486 DX66, however since the fauxpau of Vista I have decided to venture into the Mac world. Not sure if it matters but I am running a new MacBook purchased yesterday from the Mac store. Not sure what OS but I am guessing the newest. My challenge: I am trying out Parallels as I HAVE to run Outlook 2003 for work. We use ShareCalendar synchronization software for our company calendar. The problem I have run into is that I have set up the e-mail account I use to sync and can receive all day long but it will not send. I get the following error Task â€˜JBShare - Sendingâ€™ reported error (0x800CCC7D) : â€˜Your outgoing (SMTP) server does not support SSL-secured connections. If SSL-secured connections have worked in the past, contact your server administrator or Internet service provider (ISP).â€™ I know the account is set up correctly as I am using settings from my server. Just for kicks I tried setting up my gmail account as well and it get the same error regardless of what I do. I am using my home wireless network on a Linksys wireless router. There are 3 other PCâ€™s on the same network and are turned on.