Is it possible to run the AnywhereUSB 2 Plus on a Server 2008 R2 system

The current driver / Anywhere USB Manager Application download does not indicate that it will work with 2008 R2 64-bit.

legacy Windows versions not supported by Microsoft are not supported, see release notes:

SUPPORTED Operating systems

  • Microsoft Windows 7
  • Microsoft Windows 8.1
  • Microsoft Windows 10
  • Microsoft Windows Server 2012-R2
  • Microsoft Windows Server 2016
  • Microsoft Windows Server 2019

Try to update your 2008 system, or use the obsolete 2nd generation (G2) AW-USB-2 product, which uses different drivers.