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2nd Gen Ram Tech1994-2001 Rams: This section is for TECHNICAL discussions only, that involve the 1994 through 2001 Rams. For any non-tech discussions, please direct your attention to the "General discussion/NON-tech" sub sections.
It turned out to be one of the E-clips on the plunger that holds the fork in place was missing, letting the fork stay in place when the plunger pushed out to engage the 4wd.
It wound up costing me $13 for a package of random E-clips and a quart of gear lube.