Mercedes hard shifting is typical amongst the diesels, and can usually be fixed with some minor adjustments.
Have you ever flipped a car?
Bio Diesel Conversions
A common occurrence amongst Mercedes Diesels is Mercedes hard shifting between gears.
You hear the engine getting louder, and when the transmission shifts you feel like the car is being pushed backwards. It almost feels like a slight whiplash.
Shifting from 2nd into 3rd gear has to be done manually when the transmission starts to act up.
Mercedes hard shifting most of the time can be smoothed out with some adjustments. Before a mechanic try's to sell you on a rebuilt transmission try this. Take your Mercedes to a Mercedes specialist, and ask to try the following:
Tell the mechanic that your Mercedes is shifting hard between gears, and ask if an adjustment can be made. The Transmission Vacuum Modulator, Throttle pressure slide cable, or Throttle pressure cable all effect the way the transmission shifts. The transmission vacuum modulator is controlled by vacuum, and is located under the car.
If your vacuum system is out of whack it can strongly affect the way your transmission shifts. If the shift is too soft or too hard, you can change the quality of the shift by adjusting the modulator. Turning the adjustment "T" clockwise (right) will increase the pressure and harden the shift. Counter clockwise will drop the pressure and soften the shift. The throttle pressure cable is located under the hood on top of the valve cover. The throttle pressure cable tells the transmission when to shift.
If it still doesn't feel right have the mechanic continue to adjust it to your liking!