WinSCP preserves timestamps of original files by default. So their timestamps are not times of the transfer. If you want that, use -nopreservetime:
https://winscp.net/eng/docs/scriptcommand_put#nopreservetime

Thanks not what I'm finding.
The date/time stamp of the TIF file once to the SFTP site is later than the date/time stamp of the TXT file, even when the put for the TIF is executed first (as in my example).

That's what it does. WinSCP executes the commands one-by-one. No parallel transfers (or anything else) ever happens in WinSCP scripting.

Thanks for all your input Martin!

I am running a script that has the following commands:

The tif file in question is considerably larger than the text file, so it takes longer to upload to the SFTP site in question. However, the tif file is needed in order to process the text tile successfully.

Is there a command for the script to wait until the first command is successful prior to the second commend executing?
Or a confirmation command of some sort?

Thanks.