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This has baffled me for two summers now. When the truck is hot - not the engine, but the truck itself - I cannot engage cruise control. If it is a relatively cool day, I can stop after a few miles, turn the ignition off and on and most time it will then engage.
So when it is all hot, the rubber tubing is more pliable proving you have a vacuum leak showing up only then. When it is cold, the hose is more brittle and less leakage.