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A good tip is to measure preload. Put the shank in the holder and very slowly tighten the hydraulic clamping screw until the shank stops rotating.
From that point you should be able to rotate the clamp screw 2 full rotations(or more) before coming to a dead stop.
If nose diameter is not a concern for me, when should I use an "on sized" hydraulic chuck without sleeves or get an "over sized" hydraulic chuck and use sleeves?
When finishing it is best to get an on size hydraulic chuck. If you are using a 1/2" shank finisher, try to use a 1/2" hydraulic chuck. You have less chance of having any runout (Our sleeves are dead nuts, but everything has a tolerance) and you will have the best dampening available.
When you are light to medium roughing it is best to jump 1 size larger with a hydraulic chuck and use a sleeve. So if you are using a 1/2" shank tool, try to use a 5/8" or 3/4" hydraulic chuck with a sleeve to reduce it. Runout isn't much of a concern when roughing and since you are using a larger hydraulic chuck your grip will be higher. Also roughing operations have a greater chance of a tool breaking so the sleeve can act as a wear item in case the broken carbide kicks back and hits the tool holder.