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If you are seeing the front drive shaft turn,Then it is in four wheel drive, Your truck has automatic lock in hubs,The most common problem with Rangers is that the lock in hubs get worn and wont keep the axle engaged to the wheel, If you go to Auto zone they have new lock in hubs for around $50.00 Or you could up grade and get hubs that you manually turn and lock in.
Start out with buying yourself a $25 book from the Parts House. The I would go to the front HUBS, secure & safety vehicle before you do anything, Clean, Inspect, Lune & Repair front Hubs as required, get the brakes while you're there. Check your drive line, axles, u-joints etc. Clean , repair , replace as needed. Check for Tranfer case Operation. Is there power going to the front Axle when 4WD is engaged? do you feel a change when you engage the Transfer Case? Have you checked the Power on the circuits? Have you Manual or Auto-locking Front Hubs? Answer all those Questions & read before you do anything.
I had the same problem w/ my 99. If you have auto hubs, they work off a vacuum pump which is located under your air filter box..check to make sure it is working..is that is working it's on to the hubs..the locking hubs are the black caps in the center of each from wheel..they snap on and off..hard to take off without breaking a few tabs..the seal one or both may not be holding the vacuum created by the motor under the airfilter box. if one of the hubs has a vacuum leak neither side will work, it's all or nothing..aside from the electric parts on the dash and side of transmition that's about everything there is to know about 1999 ranger four wheel system.