Beatles65: Did you have the brake drums on while you where bleeding the brakes??? It really looks like you bleed the brakes with the drums off. This would allow the cylinders to over extend and blow the cups out of the bores. Then they would leak. You need the drums on and the brakes adjusted to close to tight.
If you just removed the drum after bleeding them. Then I would take it back apart and hone the bore some more. I also would get two new cups for that cylinder. You can buy just the cups and they don't cost much at all. You may have damaged one getting it in the bore.
PS. Make sure you did not put one in back wards. I have done that before. Makes you feel like an idiot when you tear it all back down because of doing that.
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Today's Featured Article - A Cautionary Tale - by Ian Minshull. In the early 1950s my father bought an Allis Chalmers B and I used it for all the row crop work with the mangolds and potatoes, rolling and the haymaking on our farm. The farm and the Allis were sold and I have spent a lifetime working on farms throughout the country. I promised myself that one day I would own an Allis. That time event
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