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Are you connecting via FTP, or SFTP/FTPS?
Have you tried a different version of WinSCP? Either an older version, or the latest 5.6.4 RC ?
Download the "portable executables." They're zip files you can unzip and run it from anywhere; it won't replace the installed version.
If you're only using FTP, there's plenty of other free FTP programs. You can use the built-in Windows command-line FTP client to test:
Other free FTP clients for Windows include Cyberduck and Filezilla:
Are you moving or drag/dropping?
Do you get an error? If so, post that (screen shot).
Do you have commander or explorer interface in WinSCP?
What are your settings under Preferences->Transfer->Drag&Drop and Background?
Then I need to try another program and re-enter passwords; which I forget
Want to avoid the missteps to gaining all the benefits of the cloud? Learn more about the different assessment options from our Cloud Advisory team.