I worked at a company where

One of the board members would hold checks and give them to his assistant to deposit maybe a couple times a year. The bank (don’t know if it was his or or the company’s) wouldn’t cash anything over six months old, so his assistant would have to ask us to replace the old checks. This happened several times. It would have been easier on all concerned if he had given them to his assistant even once every 3-4 months.

Same company. Our bank paid a check that was about ten years old and had long since been removed from the outstanding check list. We didn’t ask the bank why they honored such an old check simply because it was for less than $20 and we didn’t have time to bother with such a small amount.

At another company, we had a check cashing business try to collect on a check that had a stop payment on it. When we pointed out that the check had “Void After 90 Days” printed on it, they dropped their claim since they had cashed it well after the 90 days.