My E300 shifts hard when it's in S mode, specially from 1st to 2nd. sometimes when I'm slowing down it shifts really bad from 2nd to 1st (when first time this happened i thought got hit from the back!) like horse kick.
I'm not sure if it has anything to do with oil service. I wasnt able to check the oil cause it has no dip stick.
when I switch it to W mode it shifts fine like No signs of shifting hard at all.
I searched about it but i couldn't find anything. I'm having this problem since last year. help me out guys I don't wanna visit Stealer.

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1999 W210 E300 Turbodiesel

Totally normal. Everything you described, mine has done and does. When it doesn't shift crisply - or shift at all - then start worrying.

Our 1998 car shifts normally, up and down, in both S mode and W mode. No hard shifts at any time.

King, you are going to need to verify the trans fill level. You've got to start somewhere.

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1998 W210 diesel (wiped out by a texter)
Baum spring compressor "for rent"

one of my customers was having the same issue a while back and he brought me a spring and a check valve, "ball bearing". I pulled the oil pan and on the side of the valve body there was a plate that houses a series of these check valves. I belive it was the third one back, sure enough the spring was broken. I replaced the spring, ball valve and it shifted fine.
I have not been able to find the article that he found the information in and Peach Parts was not aware of what I was looking for. Also, be carefull to get the right spring, as I understood it there were different tensions on the springs in the various positions

In W (winter) you eliminate 1st gear. In S(summer) that includes 1st gear. So yes you have a problem with 1st gear. Drive it in W till you can fix it. Stubborn66 is on the right track.

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1979 240D Caledonia Green/cream gone
1982 240D stick Ivory/Palimino
1999 E300D White/grey

Sweet! That's all it is?

I've just left mine in 'W'. Now I know how to fix this annoyance. This isn't really a big problem for me and doesn't happen often. Just wile in parking lots and in 'S' mode and only every third blue moon.

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2013 Volkswagen Jetta Hybrid SEL Premium (Sparky)
http://badges.fuelly.com/images/smallsig-us/193500.png

It's a car not a science experiment! Open the throttle!

Strictly going by my personal experience driving mine for 14-years/129K miles:

It really depends on how you are driving the car THROUGH YOUR THROTTLE-CONTROL at those low parking lots speeds. I would say that the car is acting totally normally, reacting as to how it is being driven. At least that's what my car has evidenced since day one of owning it from new. I may be totally wrong on the 5-speed AT being electronically shift-controlled, so that may be why it seems to act up to some, when it's acting as designed. About the W - I have read that some claim much higher mpg returns using W mode too, (color me as very 0_o skeptical as to increased mpg) as well as getting rid of the OCCASIONAL/"SOMETIMES" low-speed 'whams' of 1st gear kicking-in - all contingent as to how the driver is throttling it.

As far as maintenance goes with the dipstickless '99 E300TD, I changed-out the fluid @ 100K miles, as well as replacing the sending unit that was making a corner of the pan start weeping trans fluid. If there is no fluid loss detected visually (on the ground or wet trans. assy.) then you have to rely on the trans being filled to it's correct, full level - by whoever changed it last.

It's been a bulletproof trans, just as all the MB AT trans have been in all our MB diesels dating back to '69. I'm very pleased with being able to actually feel how it shifts in this '99.

I have to say that sometimes it does shift smooth.
I dont think this problem is normal cause i remember my 98 never shifted hard.
While back I found in forums a w210 with same problem, dealer just re program the transmission computer and it worked just fine.

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1999 W210 E300 Turbodiesel

my 210 Trans shifts normally gently in W or S

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hum.....
1987 300TD 311,000M Stolen. Presumed destroyed