Its a 2001 1.8T FWD Tiptronic. If im in a driveway or somewhere similar, and let the car roll backward and get a little bit of speed (2 or 3mph) then put it into R from N, the car wont engage and keep rolling backward. Ive even revved it to to about 4k to see if its not engaging because of the rpms being too low, but nothing... then if it stops rolling, it engages. Also sometimes when I go to R the car seems to shutter (not the motor, but the driveline). Would this be an early sign of clutch or trans failure?

 

Update: The trans gurgles when its in D..

Wtf :/