The low side probably has warped plates or the clutch is otherwise binding and won't release. When you shift it to high you're trying to engage the high along with the low that won't release. The sooner you tear it down and fix it, likely the less it will cost to fix... Right now it might just be plates and seals. Eventually... someone will engage the high when it's got some inertia behind it and something will grenade to allow one of them to turn. That will be expensive.
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