What do you mean by "pull"? It is typically used for download, while you are seem to be trying to upload the latest file. Actually, why are you first downloading and then uploading? Is that intentional? Anyway, if you have problems, please attach a full session log file showing it (using the latest version of WinSCP).
To generate the session log file, use
/log=C:\path\to\winscp.logcommand-line argument. Submit the log with your post as an attachment. Note that passwords and passphrases not stored in the log. You may want to remove other data you consider sensitive though, such as host names, IP addresses, account names or file names (unless they are relevant to the problem). If you do not want to post the log publicly, you can mark the attachment as private.