Maybe when the last 20 year old cash register or scanner breaks, when the last 20 year old inventory scanning device breaks, that 30 year old shelf tag system finally bites the dust, the last sign paper with a red K logo is used, when the last store printed logo shopping bag is used- they will finally call it quits.
Not to mention those 20+ year old price scanners on the sales floor with a little green two line screen attached - those actually work quite well. Better than most of the modern fancy price scanners at Wal Mart, Macys, Target, etc. that are often broken and slow to load all the graphics, etc.
I am amazed these cash registers, inventory guns, shelf label systems, etc. even still work. I don't think they work too well but they do work... they even managed to do something with their system that it can take orders from the website and fulfill in the store using all this old equipment.
Sears technology has been updated a bit more over the years than Kmart but still not much in the past decade.