I have 97 Audi A4 2.8(Auto).
I've been to dealer too many times to find out the problem of my car and even done a transmission service for $275 although I still have warrenty on my car. Here is the problem if any smart person can help me.
In the morning, when the car is cooled down there is very hard-shift from 1st. to 2nd., and little better at 2nd. to 3rd. Thereafter, it operates perfectly wheather you stop and run again. The hard-shift happens only once or twice in a few minute when engin(may be transmission) gets cold.
Several dealer has test drove the car but they are keep telling me "NO PROBLEM!" So, they recommended me to have transmission service even the transmission does not require any service for a life time. So, I payed $275 for it. It got just little better. Definitely there is some problem.
It seems like it's not getting enough pressure.
May be valve type problem? Or some kind of sensor problem? I don't know~

Oh~ and even I warm-up the car for like 10 minutes in the morning, it's still the same. I guess over 15 minute of warm up will eliminate the problem for the morning which is crazy. And also, if you warm-up the car about 3-4 minute, and drive the car just little bit(10 feet) and stop for about 20 second will also eliminate the problem.
Thank you so much for reading this message and I'll really appreciate if someone can help me.
"PLEASE HELP!"
Thank you again!!!

 

your problem might be become even worse. It sounds like a cold operating temp problem. Perhaps then the dealer will try to fix it and you can get your $275 back.
Other thoughts: change all transmission/axle fluids to redline. I did mine and shifting SEEMED a bit smoother. Now that I think back 3 years, I did a trip to Indiana in winter and parked the A4 outside - 0 degrees in the morning. I couldn't get the car in 1st for 5 mins and had to wait for the engine to warm up. It was really notchy for a while after that. Brought it to the dealer after the trip (Texas)...and they used the famous unable to duplicate excuse on me. Someone hit my car before I could really resolve the issue and replaced it with an S4 (no problems with the 6 speed). Issues: If you change the fluids on your own, and it gets to a point the transmission problem becomes a warranty issue, Audi might try to blame it on the fluids. But I don't see how the can as long as you get the right weight and spec oil. (Just thinking out loud).

 

I also had a '99 A6 2.8 (Tiptronic). So basically the same car...

Anyway my A6 did exactly the same thing. I had it checked once at a dealer and was told it was "normal"... I also spoke to other Audi owners who had similar experiences. So I decided it wasn't a "big deal" and just forgot about it...

I am the KING of don't-know-a-thing about engines/transmitions but I think this may simply be an "idiosyncrasy" of Audi - A little "rough" when cold. Even now with my new allroad I drive it very "easy" and shift using the Tip until the needle moves out of the "cold"...