A toolholder assembly includes a toolholder body having a coolant passage and a cutting insert seated within a recess of the body. The cutting insert includes an insert orifice extending between a top face and a bottom face that aligns with the coolant passage. A lock pin includes a lock pin orifice that aligns with and is in fluid communication with the coolant passage of the body. The lock pin orifice has an outlet port to allow the fluid to flow through the lock pin orifice and exit through the outlet port. A lock pin ring includes a coolant port in fluid communication with the outlet port of the lock pin to effectively discharge cooling fluid in the direction of a cutting area of the cutting insert.