I have a Kubota B3300SU tractor/loader 33-horsepower with HST transmission.
If it is difficult to shift the range gear shift lever:
1. release the clutch pedal
2. slightly depress the speed control pedal to rotate the gears inside the transmission
3. release the speed control pedal to return engine speed to idle
4. depress the clutch pedal and then shift the range gear shift lever.
Above wording is from my Kubota B3300SU operator's manual. Instruction works perfectly on my machine.
B3300 was "tight" in respect to range shifting new, has loosened up at 100 hours and seldom requires "help" above to shift now.
A certain amount of shifting balkiness seems normal with HST transmissions. My little Kubota RTV500 gas utility vehicle, which has HST transmission, sometimes baulks in same manner. There are many posts on competitor tractor brand forums about baulkiness between HST shifts.
Do you have the operator's manual for your tractor?