I know this is simple, but have you checked your brake light switch at the pedal arm? It is the switch that kicks the cruise off, when you hit the brakes. It is a six wire switch and two are dedicated to the cruise control. The switch may be bad and need replacement or possibly adjustment. I just put one in my 86/92 retro. If it is adjustment, you can test, by putting your foot under the pedal and holding it up, while trying the cruise. If it works then, the switch is out of adjustment. May still need replacement if "barbs" are worn and won't hold it forward enough.
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86/92 Retro D-250, 5. 9 Cummins w/auto, 2wd - 256,000 / 96 Ram 1500 short bed, 318 w/auto, 4wd - 323,000 / 2000 Jeep Grand Cherokee, 4. 0 w/auto, 4wd - 251,000 Dodge/Chrysler all the way