Thanks for your post.

This issue is being tracked already:
https://winscp.net/tracker/588

Hi,

I would love this behavior:

1. I turn on synchronized browsing in "automatic mode"
2. I go to directory, that does not exist on the other side
3. Winscp temporarily disables automatic browsing, but it remains turned on
4. I browse not-matching dirs (while winscp is waiting for dirs to match again)
5. I return to dirs that match on both sides
6. Winscp detects matching dirs and re-enables synchronized browsing again
7. Synchronized browsing is on and enabled
8. I browse matching dirs and synchronized browsing behaves as normal

So I don't have to turn it on/off manually when I go out of matching dir structure and than back to it.

Does this make sense to you?
Is this "automatic mode" implementable?