Matthew,

<< And if you can, don’t be using Windows 2008 as it is way too old.  >>

As Raul indicated, 2008 R2 still has support until 2020, and they have provided updated TLS implementations that you can turn on for various services so that one is using TLS 1.2 instead of older TLS/SSL implementations.  You can use something like this utility to make sure that you're running the optimal TLS and that you've got older cipher suites turned off:

https://www.nartac.com/Products/IISCrypto

Just make sure that you review which services/applications may be affected by such a configuration change before updating anything.  Anything that uses the built-in Windows Crypto API will be possibly affected.

Tim Young
Elevate Software
www.elevatesoft.com