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What you're describing seems almost to be a a converter lock up problem...(I'm no transmission expert but we all see stuff from time to time). I would start focusing in on your valve body electronics. The solenoids my be going goofy. Find a reputable transmission shop in your area and have them check it out. Typically they'll give it a look for free to give you an idea of what's up. If the valvebody solenoids are messed up (fairly typical in early 4l60e's 93-97), the ecm may not be letting the cruise engage because it sees the the transmission in limp mode.
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