I have a 300SD 93 W140. I have only had it a few months after searching for months to find one. The engine seems to be going great (was replaced at 56k with the 'non-rodbender') with 143k. I changed the transmission oil recently hoping it would cure my problem but it has not.

Only on cold starts or after the car has sat outside when its say 40s or cooler a while the transmission going into 1st gear the first time likes to double engage. It also does it after a night in the garage which is prob in the 50s.

If I sit there and run the engine for a while (I normally let it run for at least a little bit-- say a 30-60 secs or so)and then rev the engine just a little and back up in reverse..then hold the brake down when I put it into drive and step on the gas just a little then it probably will not do the double engagement when going into first gear.

Also it may do a revving noise when going from 2nd to 3rd sometimes if its really cold out and the car has sit outside.

If I have already driven the car and its warmed up then the car goes straight into 1st and there normally isnt an issue with the 2-3rd gear bit.

I am not sure if the tranny oil was pumped out entirely.. it cost around 140 for the filter & oil. I will ask mechanic that did it (along with a greasecar conversion which is crazy how quite the engine runs on veggie oil)

Any ideas? Thanks!