Every automatic I've every driven was reluctant to shift cold. It's a result of the higher viscosity of the oil before it heats up.

Don't push it, just let it wind out a bit more. Synthetic tranny fluid will help, and will reduce the harshness of the shifts cold, too.

If your dipstick has a kink in it, it may be very difficult to get around the first bend in the tube -- try inserting it in different rotational orientations until you find the easiest, then leave it there. That's what I have to do with the 280.

Peter

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1972 220D ?? miles
1988 300E 200,012
1987 300D Turbo killed 9/25/07, 275,000 miles
1985 Volvo 740 GLE Turobodiesel 218,000
1972 280 SE 4.5 165, 000 - It runs!