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If it's not the micro switch issue I suspect if you look closely that you will find on the door side that the latch has been tripped to the closed position hence when you close the window it hits the closed latch. IIRC this happened, don't recall why, on stoutdog's 06 and we had to fiddle around a bit to get the latch to flip back to the open position so it would engage when you closed the window. I vaguely recall that the fiddling around involved applying some minor force to the latch in the open direction but am not at all sure that's a correct memory. I do know we did not have to replace the micro switch.
_________________ Sold to LOST member my 05 Ltd, GDE Stg II turbo + TCM tune, SunCoast TC w. Transgo kit, Steiger window regulators, Samcos, Fumoto valve, 2nd gen filter head with Lub. Spec. bleeder, Hayden clutch & 11 blade fan, inverted spare, P-1 battery, BF Goodrich Long Trail TAs, Etecno1 glow plugs, timing belt at 50K miles/8 yrs
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