Have you looked at the joint where the tube joins the the top of the housing, any cracking or other defects there? May have to leak test it by pulling it off; cap off the outlet to the engine and the top tube and shove it down in a drum of water upside down to see if it leaks in. Or if you have an old tire tube you could cut it near the valve stem and hose clamp it over the housing where the cup goes on. Double over the tube and clamp it shut past the valve stem. Plug off as stated above and apply pressure through the valve stem and look for leaks with soapy water. This way would not require removal.
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Today's Featured Article - Product Review: Black Tire Paint - by Staff. I have been fortunate in that two of my tractors have had rear tires that were in great shape when I bought the tractor. My model "H" even had the old style fronts with plenty of tread. My "L" fronts were mismatched Sears Guardsman snow tires, which I promptly tossed. Well, although these tires were in good shape as far as tread was concerned, they looked real sad. All were flat, but new tubes fixed that. In addition to years and years of scuffing and fading, they had paint splattered on
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