My '99 E300D turbo had a couple odd shifts and had some flaring 1-2 regardless of mode.
I took it to my friend and excellent mechanic who has vastly more knowledge than I. He spotted a leak on the connector to the transmission and noticed it was the old style, which had been upgraded by the factory. He ordered the new connector and replaced gaskets and I supplied OE fluid of the correct type also noted it has a drain plug on the torque converter, now its fixed and shifts properly 1-2 no flaring!
Also the computer readout was flaky the first time he hooked it up and following the new connector it was solid.
Incidentally look for any signs of a coke or coffee having been spilt into the shift gate on the console, mine was not one of those death spirals that have been described as a result of liquids getting into the circuit board that is located just under there, its a bad design as its not sealed well.

Awesome car, I love the '99 turbodiesel! I hope you get yours fixed properly.

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'95 E320 Wagon my favorite road car. '99 E300D wolf in sheeps body, '87 300D Sportline suspension, '79 300TD w/ 617.952 engine at 367,750 and counting!

I took liberty of highlighting the words COMPLETE STOP in tjts1's text because I was told, when I was getting an education from someone more knowledgeable than myself on these electronic trannies, that a guaranteed way to crap up your transmission in these babies was to shift gears while the car was moving, even if barely rolling that's enough to cost you thousands...it places a tremendous force on internal parts that give up and go bye-bye!
DDH

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'95 E320 Wagon my favorite road car. '99 E300D wolf in sheeps body, '87 300D Sportline suspension, '79 300TD w/ 617.952 engine at 367,750 and counting!

Thanks Zulfigar! I will look into that wiring plate you discussed!.. I have been changin out the ATF on this 'sealed for life' transmission regulalry at about 60,000 miles. I too, come to a complete stop after it won't shift into 2nd or 3rd and just let things calm down.

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dtf
1994 E320 Wagon (Died @ 308,669 miles)
1995 E300 Diesel (228,000)
1999 E300 Turbodiesel ( died @ 255,000)
2006 Toyota Tundra SR5 AC 4X4 (115,000 miles) rusted frame - sold to chop shop
2011 Audi A4 Avant (165,000 miles) Seized engine - donated to Salvation Army
BMW 330 xi 6 speed manual (175,034 miles)
2014 E350 4Matic Wagon 128,000 miles
2018 Dodge Ram 21,000 miles

The 722.6 is all electronic control, no vacuum involved.

I would get to a MB dealer or Indy and have them connect diagnostics and pull codes.

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The OM 642/722.9 powered family
Still going strong
2014 ML350 Bluetec (wife's DD)
2013 E350 Bluetec (my DD)

both my kids cars went to junkyard in 2023
2008 ML320 CDI (Older son’s DD) fatal transmission failure, water soaked/fried rear SAM, numerous other issues, just too far gone to save (165k miles)
2008 E320 Bluetec (Younger son's DD) injector failed open and diluted oil with diesel, spun main bearings (240k miles)

1998 E300DT sold to TimFreeh
1987 300TD sold to vstech

Yes, I plan to get codes pulled at next oil change in 2 weeks.
Meanwhile car is driving and shifting perfectly.
Thank you guys for all the input and comments.
Much appreciated.
jz