Yes, engine off. Does it build any pressure if you pump it a few times quickly (with bleeder closed)?

I ended up investing in a power bleeder for this job ... took a lot of the puzzle out of it. Without one I think the big key is not letting up the pedal while you have the bleeder open. Pump, pump pump pump pump, hold down pedal, open bleeder, let fluid out, close bleeder ... pump pump pump, etc.

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1987 300D, arctic white/palomino--314,000 miles
1978 240D 4-speed, Euro Delivery, light ivory/bamboo--370,000 miles
2005 Jeep Liberty CRD Limited, light khaki/slate--140,000 miles
2018 Chevy Cruze diesel, 6-speed manual, satin steel metallic/kalahari--19,000 miles
1982 Peugeot 505 diesel, 4-speed manual, blue/blue, 130,000 miles
1995 S320, black/parchment--34,000 miles (Dad's car)