It can’t hurt.
Of course, reason has to prevail in settlement negotiations, but unless you’re sure you’re at a solid impasse, it doesn’t hurt to ask yourself, Could one more move get me the finality I came for?
Ask yourself, Will the difference between the last and next offer be more or less than my expenditures between now and my next negotiation opportunity?
Carefully quantify and evaluate the results of things not playing out as you expect them to.
Factor in a decision-maker who could be contrary to an element of your burden of proof or defense.
The trick to making a satisfying last attempt is to make one that really counts. Make it something the other party would find difficult to refuse, even if it’s slightly beyond your reach, but still within reason.
Thinking past what you think is the harm in making one more move could make the difference, and the deal.