One problem related to transmission not engage has been reported for the 1999 Dodge Ram 2500. The most recently reported issues are listed below.
While driving my Dodge Ram 2500 pickup towing my horse trailer at highway speed, the overdrive 5th gear on the manual transmission disengaged and would not re-engage. I was lucky that this incident occurred when I was not in heavy traffic and could maneuver safely out of traffic to assess the situation. All other gears would engage and I had to complete my trip is 4th gear. After an inspection of transmission was completed, it was determined that the nut that holds the 5th gear in place on the transmission out-put shaft had backed off, causing 5th gear to slide rearward and disengage. Dodge has circulated a service bulletin concerning this problem (21-10-98a) and has developed a repair kit to fix the problem. Dodge failed to notify me of this potential problem. After reseaching complaints filed with NHTSA on this situation, I quickly found 10 complaints that relate to this problem. Also after talking with local transmission mechanics, I found that several similar repairs have been done locally on Dodge pickup 5-speed transmissions. This is a major safety issue and all owners of Dodges with this transmission should be made aware of the problem.