Sounds like a good way to fill with oil. I bleed them by simply pushing the ram back into the cylinder until oil starts coming back out, and reinserting the plug.
If that doesn't help, then I have to ask if you know the history of these jacks. If they've been in the wet, they may have rust inside and need polished. Or they may need rubber seals replaced.
Dad has a big 5-foot-long trolly jack he calls Bertha. He and his dad brought it home from the landfill years and years ago, they sold it to him for 3 cents a pound. Cost $6, so I am under the impression Bertha weighs in at somewhere around 200lbs. I told you all that to say this--it had to be cleaned up and all the seals replaced in it before it would work, but it is an awesome jack.
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Today's Featured Article - Hydraulics - Cylinder Anatomy - by Curtis von Fange. Let’s make one more addition to our series on hydraulics. I’ve noticed a few questions in the comment section that could pertain to hydraulic cylinders so I thought we could take a short look at this real workhorse of the circuit. Cylinders are the reason for the hydraulic circuit. They take the fluid power delivered from the pump and magically change it into mechanical power. There are many types of cylinders that one might run across on a farm scenario. Each one could take a chapter in
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