My setup is Windows 2008 server, with locally hosted Exchange 2007. I'm trying to migrate to Office 365 Business Essentials on a cutover migration. To do this, I've learned I need to enable Outlook Anywhere. To do that I need an SSL. Right now our email addresses are email@example.com Webdomain is registered through GoDaddy who also hosts our web site. We have a MX record that directs our email to mail.webdomain.org and an A record for host mail that points to our static IP. We currently have no SSL certificate anywhere that I can find. I don't know how many SSL's I need, and I don't know how to make sure I'm requesting them correctly to make sure I'm covered for the migration. I don't even know if I will need one for any longer than it takes to migrate to Office 365. Can someone help point me in the right direction?