I had my step-son pull his car into the garage when we first picked up his '86 420SEL with just over 100K miles. When he pulled out, there was a HUGE puddle of Transmission fluid. Turned out the pan gasket needed replacing (don't know why it went all of a sudden like that...). Anyway, flushed the old oil out and replaced the filter and gasket. No problem since.

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2003 E500
2002 C230 Kompressor
1986 420SEL