I have had this problem on my 1986 190E 2.3-16 a number of times. I first blamed it on the German mechanic who did the first oil change on the car. The next time there was no one to blame but me. This car has a very long threaded section on the drain plug and I decided it was too much trouble and bought a device to suck the old oil out the dipstick tube. Works great. I still have a spare plug in the glove box, but I doubt I will ever need it. Jim

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Own:
1986 Euro 190E 2.3-16 (291,000 miles),
1998 E300D TurboDiesel, 231,000 miles -purchased with 45,000,
1988 300E 5-speed 252,000 miles,
1983 240D 4-speed, purchased w/136,000, now with 222,000 miles.
2009 ML320CDI Bluetec, 89,000 miles

Owned:
1971 220D (250,000 miles plus, sold to father-in-law),
1975 240D (245,000 miles - died of body rot),
1991 350SD (176,560 miles, weakest Benz I have owned),
1999 C230 Sport (45,400 miles),
1982 240D (321,000 miles, put to sleep)