Early one Saturday morning, in Waterloo station, I used a machine to buy a cheap off peak day return to Southampton. I could not get through the barrier to the platform. The staff at the barrier explained that the ticket I had bought was valid only on the long route from London Bridge via Brighton to Southampton. That takes one hour longer than the direct route from Waterloo.
I asked why you can buy a ticket for what was, to my mind an obvious Waterloo Southampton route, from a machine in Waterloo, which does not allow me to depart from Waterloo. There was no answer.
I could not get a refund from a machine or exchange it for another ticket there and then.
The staff opened the barrier for me so that I could take the direct train which was leaving in 5 minutes, and he explained that I had better not be caught, and that I had better return on the Brighton route.
Fortunately (unfortunately for others) as my return time approached and I entered Southampton station, the Brighton London line was closed for an emergency, and my ticket became valid on "any reasonable route". That happened to be the direct train which was the one I wanted in the first place.
Waterloo, early morning, no ticket office staff and lousy unhelpful machines . . . and that was in 2004.
Saving grace - a real person with a touch of humanity.
Machines will only be any good when fare structures and routing are simplified, and they will never be as good as a human who knows the railways.