300E, 4matic, 1991, 131K miles. Transmission will not shift into 4th and sometimes it won't shift into 3rd. If you place selector into 2nd and return it to 4th before starting off, it consistently shifts from 1st to 2nd. Neutral and reverse can be selected and work appropriately. I've checked fluid level and vacuum connection. Fluid had a normal color and smell. I was going to drop pan next and check for metal. What are the probable causes. What should I try or check next?

The exact same thing happened to me, and It was the clutch pack on 4th gear. 3rd was on its way out. The car would shift into Reverse, drive, and 1/2/3 fine, but 4th would just not engage. 3rd would also occasionally not engage while this was happening.

My mechanic dropped the pan, and found the clutch packs were gone for fourth gear and third was on its way out.

Unfortunately My mechanic had to rebuild the tranny.

IT was not too expensive compared to the MB Dealer, and I had other stuff done. I figured the tranny apart from the other stuff was around $1500 to get done.

I hate to be the bearer of bad news, but you just might be in need of a tranny rebuild.

Alon

What did you get done to your tranny? My tranny is out too. Doesn't go into any gears above 1st. Any suggestions where to get my tranny rebuilt?