The primary purpose of the "Time" column is to show estimated time.
It says only "Time", not "Estimated", because it shows only elapsed time, when user explicitly turns off calculating total transfer size:
https://winscp.net/eng/docs/ui_transfer_custom
So the user knows, what it shows. The title can be possibly updated depending on the above setting state. It's just that if you change the option in the middle of a transfer, the column value meaning will indeed differ among transfers. But just temporarily.
I have updated the documentation to include this:
https://winscp.net/eng/docs/ui_queue
Also, I do not think that anyone really needs to see both elapsed and estimated time at the same time.
Anyway, if it shows 00:00:00 all the time for you, it's indeed wrong. Can you possibly record a video of what you are doing? E.g. using screenr.com or similar service.