Please disregard. It was user error. I think what happened is that while I was trying to get the filemask right, I was inadvertently debugging the wrong script. I went back to generate the log when I noticed, and now my filemask is working as expected.

*hangs head in shame*

Thanks so much for the reply and attentiveness though!

Your syntax looks good.

Please attach a full log file showing the problem (using the latest version of WinSCP).

I am setting up an automated backup for a remote server. I want to have a complete backup first, but then subsequent synchronizations should skip certain directories. It appears though that as long as the directory exists on the local side, it will still scan the directory on the remote server – even with the -filemask="|*/largedirectory/"

If I delete the local version, it will skip scanning it as expected.

Is there any way to keep the local copy but force it to skip scanning the remote folder?

My command looks like:
synchronize local -criteria=Both -filemask="| */largedirectory/"

Cheers!