Does the shudder normally happen overnight? I mean literally overnight. One day smooth and the next a distinct shudder.

If it does then what are the ramifications? Catastrophic failure or a slow loss of reverse?

Right now it will put plenty of tq to the pavement in reverse.

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1984 300 SD, 2 tank WVO
1996 Ram Cummins, 2 tank WVO,
2004.5 Ram Cummins, 2 tank WVO