Given some function of proper time which expresses the rate at which the string is being unreeled, there will be a time \tau_{crit} after which no signal from the point of unreeling can reach the object at the end of the string before it passes through the horizon.
After \tau_{crit}, the only way to keep the string from eventually breaking (assuming it hasn't broken already) will be to continue to feed it out at an increasing rate. Clamping the string, attempting to pull the object back up, or even just feeding out the string at a constant rate, will all ultimately cause the string to break, though the exact time when that happens will depend on the physical properties of the string.