I am a newbie to RPi and been hacking at Arduino for about a year, came across your post while researching interfacing them for wireless data transfer.
I recently set up SAMBA and accomplished SMB file transfer TO
the RPi. This was done from a Copier/Scanner device with SMB Send scripted into it's functionality. The share on the RPi is easy to get files into, but the sharename wasn't as expected, in case you try, browsing the share will help determine that.
However, using the SMBClient, you may be able to go the other way INTO a Windows share, barring any protocol conflict with what SMB dialects Windows will accept. It may help to create a Windows user with the same credentials as the RPi login with Full Read/Write rights to the shared folder. Otherwise you may need to explicitly provide UName/PWrd credentials of the Windows User in your script.
As for the 'Automatic' part, I imagine you would need to write that into a shell script along with the transfer command i.e.:
$ smbclient //server/share -c 'cd c:/remote/path ; put local-file remote-file'
Here is the link with info I used to set up SAMBA on the RPi:
http://raspberrypihq.com/how-to-share-a ... pberry-pi/
If you run into this subject in an FTP post(like I did), you can do all this with FTP as well over your local network
, but setting up FTP on Windows is an extra step, best accomplished with third party FTP software, a whole different topic.