Use Transfer each file individually option:
https://winscp.net/eng/docs/ui_copy

This only works with multiple files selected.

Not with one directory with many subdirs as stated above. :(

Use Transfer each file individually option:
https://winscp.net/eng/docs/ui_copy

A request to do this recursively is tracked here:
https://winscp.net/tracker/875

Hi, is there any way to have Win SCP automatically transfer multiple files from the same subfolder?

Most frequently I am uploading folders with multiple tiers of subfolders and files. The process is greatly extended when only one file per subfolder is uploaded at a time. Individually starting a separate upload per subfolder is also inconvenient.