SBS 2008 and the RWW issue
Install the cumulative update KB3197954 released on 10/27/2016 (in addition to the flash update that also came out out of band)
If you are STILL having issues connecting via RWW AFTER this update PLEASE let me know.
Addressed connectivity issue from a 32-bit application to a Remote Desktop Gateway that doesn’t have HTTP tunneling enabled.
October 27, 2016—KB3197954 (OS Build 14393.351)