Updates Tab (Preferences Dialog)

Select how often should WinSCP automatically check for application updates. Select Never to disable automatic check. Note that you can instruct WinSCP to do check on your request.

WinSCP connects to the WinSCP site using HTTP protocol to check for updates. By default WinSCP will try to automatically detect what is your proxy settings for HTTP protocol. If the detection fails, you need to check Use proxy server and fill your Proxy host name and Port number.