The /upload switch does not support wildcards.
For wildcards you need to use scripting.
See https://winscp.net/eng/docs/guide_automation

This has two parts. Here is the test line I am using to try and upload files to a remote FTP Server:


When I run this in the commandline I will get a window open that tells me it cannot find the file specified (*.txt)

How do I specify a wildcard set of files on the command line for I really do not want to create scripts to manage along with bat files. I have looked through the documentation but did not see any specific example that addresses this question.