You can use synchronization for the purpose. You can automate that with scripting or /synchronize option.

A really cool feature would be to allow WinSCP to associate
a particular remote directory tree with a particular
local directory and thus allow one-click path-adjusted
transfers of files within those directories.


So if for example, if I associate:

sftp://website.com/public_html/site_a

with

c:\webprojects\site_a


I can update the file

sftp://website.com/public_html/site_a/info/info-1.html

with just one click on:

c:\webprojects\site_a\info\info-1.html

without bothering to specify exactly where under

sftp://website.com/public_html/site_a/

I want to upload to.


Right now, using Send To integration you still have to
specify the directory you wish to upload to for each and
every time you upload.