You can start it in a new window.
https://winscp.net/eng/docs/ui_keepuptodate#buttons

You can also start the function from the command-line. So you can create a (desktop) shortcut to start everything on a single double-click:
https://winscp.net/eng/docs/commandline#operations

Thanks. I was looking for an option that would do this automatically rather than requiring me to select this option each time I start the app.

When I do select this option after connecting to a server, it displays a dialog of options and I click Start. It then leaves the modal dialog open over the UI and I can't access the rest of WinSCP.

Would this help?
https://winscp.net/eng/docs/task_keep_up_to_date

Hi,

I'm new to WinSCP and I've been able to edit a remote file and have it auto-update after saving the file, but I'm wondering if it's possible to edit a local copy of a file and have it update to the connected server after saving the local copy?

I saw the synchronization menu option but I don't want to synchronize everything so I'm really looking for uploading of the local file I just saved.

Thanks!